IMIDAZOPYRIDINES AND IMIDAZOPYRIMIDINES AS HIV-I REVERSE TRANSCRIPTASE INHIBITORS

Title:

IMIDAZOPYRIDINES AND IMIDAZOPYRIMIDINES AS HIV-I REVERSE TRANSCRIPTASE INHIBITORS

Document Type and Number:

WIPO Patent Application WO/2010/032195

Kind Code:

Abstract:

The invention provides compounds of formula A or B which are useful in the treatment of a subject infected with HIV.

Inventors:

BODE, Moira, Leanne (581 Kyalami Estates, 1684 Midrand, ZA)
ROUSSEAU, Amanda, Louise (9 Hathersage Close, 13A Oxford Road, 2047 Bedford Gardens, ZA)
GRAVESTOCK, David (22 Sanford Glen, 2nd Avenue Ravenswood, 1459 Boksburg, ZA)
MOLEELE, Simon, Sana (1691 Mahlangu Street, Pretoria North, 1818 Soweto, ZA)
VAN DER WESTHUYZEN, Christiaan, Wynand (46 Appelgrein Street, Brackenhurst, 1448 Alberton, ZA)

Application Number:

IB2009/054021

Publication Date:

March 25, 2010

Filing Date:

September 15, 2009

Export Citation:

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Assignee:

CSIR (Scientia, 0002 Pretoria, ZA)
BODE, Moira, Leanne (581 Kyalami Estates, 1684 Midrand, ZA)
ROUSSEAU, Amanda, Louise (9 Hathersage Close, 13A Oxford Road, 2047 Bedford Gardens, ZA)
GRAVESTOCK, David (22 Sanford Glen, 2nd Avenue Ravenswood, 1459 Boksburg, ZA)
MOLEELE, Simon, Sana (1691 Mahlangu Street, Pretoria North, 1818 Soweto, ZA)
VAN DER WESTHUYZEN, Christiaan, Wynand (46 Appelgrein Street, Brackenhurst, 1448 Alberton, ZA)

International Classes:

C07D471/04; A61K31/437; A61K31/519; A61P31/18; C07D487/04

Attorney, Agent or Firm:

FORBES, Craig, Paul et al. (Adams & Adams, Adams & Adams Place1140 Prospect Street, Hatfield,PO Box 1014, Pretoria 0001, ZA)

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Claims:

CLAIMS

1. A compound selected from compounds of formula A or formula B

in which, for formula A,

R is selected from alkyl, branched alkyl, cycloalkyl, aryl, substituted aryl, naphthyl, benzyl, adamantyl and polycycloalkyl, R¹ is selected from alkyl, cycloalkyl, substituted alkyl, branched alkyl, phenyl, substituted phenyl, substituted benzyl, heteroaryl, substituted heteroaryl, oxacycloalkyl, bicycloalkyl, furyl, substituted furyl, thienyl and substituted thienyl, isoxazolyl, substituted isoxazolyl

R² - R⁵ are independently selected from H, halogen, cyano, alkoxy, aryloxy, substituted aryl, alkyl and substituted alkyl, or R² and R³ together form a carbocyclic ring or, independently, R⁴ and R⁵ together form a carbocyclic ring, R⁶ is H, alkyl or alkanoyl, provided that

(a) if R is cyclohexyl and R²-R⁶ are H, then R¹ is not 2-bromophenyl, 3- bromophenyl, 2-chlorophenyl, 3-chlorophenyl, 2-trifluoromethylphenyl, 2,4- dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 4-fluorophenyl, isopropyl, 2-furyl, 2-hydroxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl or 2-fluorophenyl;

(b) if R is cyclopentyl and R²-R⁶ are H, then R¹ is not 2-bromophenyl, 3- bromophenyl, 2-chlorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6- difluorophenyl, 2,4-difluorophenyl, 2-trifluoromethylphenyl or 2-fluorophenyl; (c) if R is cyclohexyl or cyclopentyl and R³, R⁴, R⁵ and R⁶ are H, and R² is methyl, then R¹ is not 2-chlorophenyl; (d) if R is cyclohexyl or cyclopentyl and R², R⁴, R⁵ and R⁶ are H, and R³ is methyl then R¹ is not 2-chlorophenyl;

(e) if R is cyclohexyl or cyclopentyl and R², R³, R⁵ and R⁶ are H, and R⁴ is methyl then R¹ is not 2-chlorophenyl; (f) if R is cyclohexyl or cyclopentyl, and R², R³, R⁴ and R⁶ are H, and R⁵ is methyl, ethyl or trifluoromethyl, then R¹ is not 2-chlorophenyl, 2-fluorophenyl, 2,6- difluorophenyl, 2-fluoro-5-methylphenyl, 2-fluoro-6-methoxyphenyl, 2,6-difluoro-4- methoxyphenyl, 2,4-difluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-pyridinyl, 2-fluoro-4-pyridinyl or 2-chloro-6-fluorophenyl; (g) if R is cyclohexyl, and R², R³ and R⁵ are H, and R⁴ is fluorine, chlorine or bromine, then R¹ is not 2-chlorophenyl;

(h) if R is cyclohexyl, and R³ and R⁵ are methyl and R², R⁴ and R⁶ are H R¹ is not 2-chlorophenyl; and in which, for formula B, R is cycloalkyl and R¹ is substituted aryl,

2. A compound as claimed in claim 1 , in which the alkyl and branched alkyl groups of R¹ are substituted by one or more heteroatoms selected from oxygen, nitrogen and sulphur.

3. A compound as claimed in claim 1 or claim 2, in which the phenyl group is substituted by one or more substituents selected from halogen, hydroxy, alkyl, alkoxy, cyano, substituted alkyl, halo or nitro.

4. A compound as claimed in any one of claims 1 to 3 inclusive, in which the heteroaryl group is selected from oxazolyl, isoxazolyl, substituted isoxazolyl, substituted furanyl, furanyl, and substituted thienyl groups.

5. A compound as claimed in any one of claims 1 to 4 inclusive, in which the halogen is selected from one or more of F, Cl and Br.

6. A compound as claimed in any one of claims 1 to 5 inclusive, in which the cycloalkyl group is selected from C3-C6 cycloalkyl groups, oxacycloalkyl groups and adamantane.

7. A compound as claimed in any one of claims 1 to 6 inclusive, in which the branched alkyl groups are selected from C₂ to C₁₂ branched alkyl groups.

8. A compound as claimed in any one of claims 1 to 7 inclusive, in which the compounds of formula A are selected from compounds in which:

(a) R is selected from ethyl, 2-morpholinoethyl, 1 -butyl, 2-pentyl, 1-pentyl, 1 ,1 ,3,3-tetramethylbutyl, isopropyl, cyclohexyl, cyclopropyl, 4-(3,4- dichlorophenoxy)butyl, 1-adamantyl, 4-methoxyphenyl, 2-naphthyl, benzyl, A- chlorobenzyl, 2-chloro-6-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, cyclopentyl; (b) R¹ is selected from ethyl, 2-(methylthio)ethyl, 1 -propyl, 2-butyl, 2-methyl-

1 -propyl, 2, 2-dimethyl-1 -propyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-pentyl, 2-pentyl, 3-pentyl, te/t-butyl, isopropyl, isobutyl, 1-octyl, 1-phenylethyl, 2-hydroxyphenyl, A- hydroxyphenyl, 4-methoxyphenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-nitrophenyl, 2-fluorophenyl, A- fluorophenyl, 3-ethoxy-4-hydroxy-phenyl, 4-dimethylaminophenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxy-4-hydroxyphenyl, 4-benzyloxyphenyl, 2,4-dimethoxyphenyl, 4-hydroxy-3- methoxy-phenyl, 3-hydroxy-4-methoxy-phenyl, 2,3,6-trichlorophenyl, 2-fluoro-(3- methoxy)phenyl, 3-chloro-2-fluoro-phenyl, 2-trifluoromethylphenyl, A- trifluoromethylphenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 2,5-dichlorophenyl, 2,6- dichlorophenyl, 2,6-difluorophenyl, 4-chloro-3-fluoro-phenyl, 2-chloro-6-fluoro-5-methyl- phenyl, 3-(5-methyl)isoxazolyl, 2-(5-hydroxymethyl)furanyl, 2-furanyl, 2-(5- chloro)furanyl, 2-(5-ethyl)thienyl, 2-(3-methyl)thienyl, 2,4,5-trifluorophenyl, 3-(2,5- dimethoxy)tetrahydrofuranyl, 4-cyanophenyl, 3-cyanophenyl, norpinenyl; (c) R² is selected from H, benzyloxy, methyl, chloro; (d) R³ is selected from H, methyl, chloro;

((ee)) RR⁴⁴ iiss sseelleecctteedd ffrroormr H, chloro, fluoro, methyl, bromo, nitrile, 2- methylphenyl, 4-methoxyphenyl,

((ff)) RR⁵⁵ iiss sseelleecctteedd ffrroomm H, methyl, chloro, bromo, 2-methylphenyl, phenyloxy, 4-methoxyphenyl, ethoxy, cyano; (g) R⁶ is selected from H, ethyl, acetyl,

(h) R⁴ and R⁵ together form an aromatic ring.

(i) R² and R³ together form an aromatic ring.

9. A compound as claimed in any one of claims 1 to 8 inclusive, which is selected from compounds 1 to 194 of Scheme 2.

10. A composition for use in treating a subject infected with HIV, the composition including a compound of any of claims 1 to 9 inclusive

11. Use of a compound of any of claims 1 to 9 inclusive, in the preparation of a medicament for the treatment of an HIV infection.

Description:

IMIDAZOPYRIDINES AND IMIDAZOPYRIMIDINES AS HIV-I REVERSE TRANSCRIPTASE INHIBITORS

THIS INVENTION relates to compounds and compositions having activity against the enzyme HIV-1 reverse transcriptase.

Highly active antiretroviral treatment (HAART) is a treatment regimen for HIV-

AIDS sufferers which combines a cocktail of antiretroviral drugs chosen from a number of different classes. One of these classes comprises the non-nucleoside reverse transcriptase inhibitors (NNRTIs). These drugs act by inhibiting the enzyme HIV-1 reverse transcriptase. This enzyme is a validated target for the development of anti-HIV drugs. There are a number of NNRTIs that are FDA approved and one of these drugs generally forms part of the first-line treatment regimen against HIV-AIDS. There are a number of advantages associated with this class. One of the advantages is the excellent selectivity index (ratio of 50% cytotoxic concentration to 50% antivirally effective concentration) displayed by these drugs, which is usually of the order of 10,000-100,000. This high selectivity makes the NNRTI class the least toxic of the clinically approved antiretrovirals and makes these drugs suitable for use in the prevention of mother to child transmission. The reason for the high selectivity is the fact that NNRTIs only recognise and bind to HIV-1 reverse transcriptase, not to any other RTs or DNA or RNA polymerases. These drugs act by binding to a lipophilic, non- substrate binding pocket located about 1θA from the substrate binding site. This binding results in conformational changes within the reverse transcriptase catalytic site that leads to a dramatic slowing down of the catalytic activity. The allosteric inhibitors of reverse transcriptase (RT) possess very different structural characteristics and as many as 50 diverse structural classes have been found to have activity against reverse transcriptase. The first generation of NNRTIs (exemplified by nevirapine and delavirdine) is sensitive to the development of drug resistance and even a single amino acid mutation in the NNRTI binding region of RT confers a high level of drug resistance. There is accordingly a requirement for NNRTIs which can inhibit as many different RT mutants as possible. The applicant is aware of PCT/US2008/082531 entitled "Non-nucleoside reverse transcriptase inhibitors" (filed on 5 November 2008) which claims the priority of

USSN 60/986,990 (filed on 9 November 2007). The generic structure disclosed in this document covers a very large number of compounds. The document specifically discloses about 1 1600 compounds. However, inhibition data are provided for only about 30 compounds. The generic disclosure of the present application covers a substantially smaller number of compounds and those compounds of

PCT/US2008/082531 which fall within the scope of the generic structure of the present application have been excluded by the introduction of provisos.

According to a first aspect of the invention there is provided a compound selected from compounds of the formula A or B

A B

in which, for formula A, R is selected from alkyl, branched alkyl, cycloalkyl, aryl, substituted aryl, naphthyl, benzyl, adamantyl and polycycloalkyl,

R ¹ is selected from alkyl, cycloalkyl, substituted alkyl, branched alkyl, phenyl, substituted phenyl, substituted benzyl, heteroaryl, substituted heteroaryl, oxacycloalkyl, bicycloalkyl, furyl, substituted furyl, thienyl and substituted thienyl, isoxazolyl, substituted isoxazolyl

R ² - R ⁵ are independently selected from H, halogen, cyano, alkoxy, aryloxy, substituted aryl, alkyl and substituted alkyl, or R ² and R ³ together form a carbocyclic ring or, independently, R ⁴ and R ⁵ together form a carbocyclic ring,

R ⁶ is H, alkyl or alkanoyl, provided that (a) if R is cyclohexyl and R ²-R ⁶ are H, then R ¹ is not 2-bromophenyl, 3- bromophenyl, 2-chlorophenyl, 3-chlorophenyl, 2-trifluoromethylphenyl, 2,4- dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 4-fluorophenyl, isopropyl, 2-furyl, 2-hydroxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl or 2-fluorophenyl;

(c) if R is cyclohexyl or cyclopentyl and R ³, R ⁴, R ⁵ and R ⁶ are H, and R ² is methyl, then R ¹ is not 2-chlorophenyl;

(d) if R is cyclohexyl or cyclopentyl and R ², R ⁴, R ⁵ and R ⁶ are H, and R ³ is methyl then R ¹ is not 2-chlorophenyl; (e) if R is cyclohexyl or cyclopentyl and R ², R ³, R ⁵ and R ⁶ are H, and R ⁴ is methyl then R ¹ is not 2-chlorophenyl;

(f) if R is cyclohexyl or cyclopentyl, and R ², R ³, R ⁴ and R ⁶ are H, and R ⁵ is methyl, ethyl or trifluoromethyl, then R ¹ is not 2-chlorophenyl, 2-fluorophenyl, 2,6- difluorophenyl, 2-fluoro-5-methylphenyl, 2-fluoro-6-methoxyphenyl, 2,6-difluoro-4- methoxyphenyl, 2,4-difluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-pyridinyl,

2-fluoro-4-pyridinyl or 2-chloro-6-fluorophenyl;

(g) if R is cyclohexyl, and R ², R ³ and R ⁵ are H, and R ⁴ is fluorine, chlorine or bromine, then R ¹ is not 2-chlorophenyl;

(h) if R is cyclohexyl, and R ³ and R ⁵ are methyl and R ², R ⁴ and R ⁶ are H R ¹ is not 2-chlorophenyl; and in which, for formula B, R is cycloalkyl and R ¹ is substituted aryl.

The alkyl and branched alkyl groups of R ¹ may be optionally substituted by one or more heteroatoms. The heteroatoms may be oxygen, nitrogen or sulphur. For example the alkyl group may be substituted by a thiomethyl group. The substituted alkyl group may, therefore, be a 2-thiomethylethyl group. The phenyl group may optionally be substituted by one or more substituents selected from halogen, OH, alkyl, alkoxy, cyano, amino, substituted alkyl, halo or nitro. The heteroaryl group may be an O, N or S heteroaryl group and may, for example, be selected from oxazolyl, isoxazolyl, substituted isoxazolyl, furanyl, and thiophenyl groups.

The halogen may be selected from one or more of F, Cl and Br. The cycloalkyl group may be selected from C3-C6 cycloalkyl groups and adamantane. For example, the cycloalkyl group may be a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or tetrahydrofuranyl group.

The alkyl and branched alkyl groups may be selected from C ₂ to C ₁₂ alkyl and branched alkyl groups. Preferred alkyl and branched alkyl groups include 2-pentyl, 1 -butyl, 2-propyl, 2-butyl and 1-pentyl and 1-octyl.

Examples of preferred compounds of the invention, of formula A are compounds in which:

(a) R is selected from ethyl, 2-morpholinoethyl, 1 -butyl, 2-pentyl, 1-pentyl, 1 ,1 ,3,3-tetramethylbutyl, isopropyl, cyclohexyl, cyclopropyl, 4-(3,4- dichlorophenoxy)butyl, 1-adamantyl, 4-methoxyphenyl, 2-naphthyl, benzyl, A- chlorobenzyl, 2-chloro-6-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, cyclopentyl; (b) R ¹ is selected from ethyl, 2-(methylthio)ethyl, 1 -propyl, 2-butyl, 2-methyl-

1 -propyl, 2, 2-dimethyl-1 -propyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-pentyl, 2-pentyl, 3-pentyl, te/t-butyl, isopropyl, isobutyl, 1-octyl, 1-phenylethyl, 2-hydroxyphenyl, A- hydroxyphenyl, 4-methoxyphenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-nitrophenyl, 2-fluorophenyl, A- fluorophenyl, 3-ethoxy-4-hydroxy-phenyl, 4-dimethylaminophenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxy-4-hydroxyphenyl, 4-benzyloxyphenyl, 2,4-dimethoxyphenyl, 4-hydroxy-3- methoxy-phenyl, 3-hydroxy-4-methoxy-phenyl, 2,3,6-trichlorophenyl, 2-fluoro-(3- methoxy)phenyl, 3-chloro-2-fluoro-phenyl, 2-trifluoromethylphenyl, A- trifluoromethylphenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 2,5-dichlorophenyl, 2,6- dichlorophenyl, 2,6-difluorophenyl, 4-chloro-3-fluoro-phenyl, 2-chloro-6-fluoro-5-methyl- phenyl, 3-(5-methyl)isoxazolyl, 2-(5-hydroxymethyl)furanyl, 2-furanyl, 2-(5- chloro)furanyl, 2-(5-ethyl)thienyl, 2-(3-methyl)thienyl, 2,4,5-trifluorophenyl, 3-(2,5- dimethoxy)tetrahydrofuranyl, 4-cyanophenyl, 3-cyanophenyl, norpinenyl; (c) R ² is selected from H, benzyloxy, methyl, chloro; (d) R ³ is selected from H, methyl, chloro;

((ee)) RR ⁴⁴ iiss sseelleecctteedd ffrroormr H, chloro, fluoro, methyl, bromo, nitrile, 2- methylphenyl, 4-methoxyphenyl,

((ff)) RR ⁵⁵ iiss sseelleecctteedd ffrroomm H, methyl, chloro, bromo, 2-methylphenyl, phenyloxy, 4-methoxyphenyl, ethoxy, cyano; (g) R ⁶ is selected from H, ethyl, acetyl,

(h) R ⁴ and R ⁵ together form an aromatic ring.

(i) R ² and R ³ together form an aromatic ring.

According to a second aspect of the invention there is provided a composition for use in treating a subject who has been infected with HIV, the composition including a compound selected from compounds of formula A or B as described above.

According to a third aspect of the invention there is provided a substance or composition for use in a method of treating a subject who has been infected by HIV, the substance or composition including a compound selected from compounds of formula A or B as described above.

According to a fourth aspect of the invention, there is provided the use of a compound selected from compounds of formula A or B as described above in the manufacture of a medicament for the treatment of a subject infected with HIV.

The compounds of the invention have been found to have activity against the enzyme reverse transcriptase in the μ-molar range. In addition these compounds have been found to be active against HIV in the whole cell PBMC or MAGI anti-HIV assay in the μM to nM range.

According to a fifth aspect of the invention there is provided a method of treating a subject who has been infected by HIV, the method including administering to a subject in need of treatment a compound selected from compounds of formula A or B as described above.

The compounds of the invention can readily be prepared in one step by an acid-catalysed three-component coupling reaction as shown in Scheme 1 in which a 2- aminopyridine or a substituted 2-aminopyridine, in which R, R ¹, R ², R ³, R ⁴ and R ⁵ are as hereinbefore described, is reacted with an aldehyde and an isonitrile in the presence of montmorillonite K-10 clay or any other suitable acid catalyst at 95-100 ⁰C for 5-8 hours under conventional heating or 15-30 min under microwave irradiation. The product is generally isolated by column chromatography.

Scheme 1. Preparation of imidazo[1 ,2-a]pyridines

Thus according to a sixth aspect of the invention, there is provided a method of synthesising a compound selected from compounds of formula A or B as described above, which includes the step of condensing a 2-aminopyridine or a substituted 2- aminopyridine of the formula

or 2-aminopyrimidine with an aldehyde of the formula R ¹CHO and an isocyanide of the formula RNC in which R, R ¹, R ², R ³, R ⁴, R ⁵ and R ⁶ are as described above.

Examples of the compounds of the invention are set out in Scheme 2. Scheme 2

13 14 15

MLB133-6D7B

17 18 19 20

21 22 23 24

MLB133-635A MLB133-634C MLB133-635B MLB133-636B

MLB133-650A

2-49694 DG 402-49700 DG 402-49702 DG 402-49704

93 94 95 96 SG389-812 SG389-834B SG389-816B SG389-816C

117 118 119 120 The invention is now described, by way of example with reference to the following Examples.

All compounds were prepared by one of four methods

Method 1

The appropriate 2-aminopyridine (1.33 mmol), aldehyde (1.33 mmol) and isocyanide (1.36 mmol) in dioxane (2.5 ml) were heated in the presence of montmorillonite K-10 clay (250 mg) for 5 - 8 h at 95 - 100 ⁰C. After reaction, the liquid was filtered from the clay and the clay was rinsed with dioxane or ethyl acetate (2 x 2.5 ml). The solvent was removed in vacuo and the residue purified by column chromatography (elution hexane: ethyl acetate) to afford the required product.

Method 1 applies to compounds: 1-15, 17-31 , 33-41 , 43, 49-64, 67-77, 106-1 10, 112- 115 and 117-183.

Method 2

As for method 1 , but instead of heating, the reaction was stirred at room temperature for 48 h.

Method 2 applies to compounds: 45-47

Method 3

As for method 1 , but instead of conventional heating, reaction components were reacted under microwave irradiation at 150W and 100 ⁰C for 15-30 min in a sealed pressure tube.

Method 3 applies to compounds: 42, 44, 48, 65, 66, 78-105, 1 11 , 1 16, 186-194. In the case of the pyrimidine 193, the appropriate 2-aminopyrimidine (1.33 mmol) and aldehyde (2.66 mmol) were microwaved at 150 W power and 150 ⁰C for 35 min without solvent. Isocyanide (1.60 mmol), dioxane (1.5 ml) and montmorillonite K-10 clay (250 mg) were then added and irradiated at 150W and 100 ⁰C for 25 min. After reaction, the liquid was filtered from the clay and the clay was rinsed with dioxane or ethyl acetate. The solvent was removed in vacuo and the residue purified by column chromatography (elution ethyl acetate) to afford the required product.

Method 4 lmidazo[1 ,2-a]pyridines prepared by method 1 or 3 were further modified to produce compounds 16, 32, 184 and 185. Preparations are described below.

N-butyl-N-(2-isopropylimidazo[1 ,2-a]pyridin-3-yl)acetamide 16

N-butyl-2-isopropylimidazo[1 ,2-a]pyridin-3-amine 5 (250 mg, 1.08 mmol) was reacted with acetyl chloride (2 eq., 2.16 mmol, 154μl) in the presence of K ₂CO ₃ (2 eq., 2.16 mmol, 299 mg) in acetonitrile (10 ml) at room temperature. The reaction progress was monitored by TLC. Purification of the product was achieved by column chromatography, eluting with ethyl acetate: hexane.

N-butyl-N-ethyl-2-isopropylimidazo[1 ,2-a]pyridin-3-amine 32

N-butyl-N-(2-isopropylimidazo[1 ,2-a]pyridin-3-yl)acetamide 16 (287 mg, 1.05 mmol) was reacted with LiAIH ₄ (2 eq., 2.10 mmol, 80 mg) in THF (10 ml) at room temperature. Progress of the reaction was monitored by TLC. Aqueous NaOH solution was used to quench the reaction. Solids were filtered and washed with ethyl acetate and the product was purified by column chromatography, eluting with ethyl acetate.

2-(2-chlorophenyl)-N-cyclohexyl-5-phenoxyimidazo[1 ,2-a]pyridin-3-amine 184 Phenol (40.43 mg, 0.687 mmol) was dissolved in DMF (5 ml) and sodium metal (10.31 mg, 0.687 mmol) was added portion-wise. 5-Bromo-2-(2-chlorophenyl)-N- cyclohexylimidazo[1 ,2-a]pyridin-3-amine 42 (139.1 mg, 0.344 mmol ) was added to this sodium phenoxide solution and heated at 90 ⁰C for 4 h. The reaction was quenched with water and extracted into ethyl acetate. The product was purified by column chromatography, elution ethyl acetate: hexane.

2-(2-chlorophenyl)-N-cyclohexyl-5-ethoxyimidazo[1 ,2-a]pyridin-3-amine 185

5-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine 42 (152 mg, 0.376 mmol) was added to sodium ethoxide [generated in situ by addition of sodium metal (17.32 mg) to absolute ethanol (10 ml)]. The mixture was heated under reflux for 8 h. Excess solvent was removed in vacuo and the resultant mixture was treated with water before been extracted into ethyl acetate, dried over magnesium sulphate and filtered. Excess solvent was removed under reduced pressure to give an oil that was purified by column chromatography, eluting with hexane: ethyl acetate.

The analytical data of compounds 1-194 are set out below.

1 MLB133-607A N-cyclohexyl-2-cyclopropylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.05 - 7.94 (m, 1 H), 7.46 - 7.33 (m, 1 H), 7.01 (ddd, J =

1.3, 6.7, 9.0, 1 H), 6.69 (td, J = 1.0, 6.7, 1 H), 3.07 - 2.67 (m, 2H), 2.1 1 - 1.82 (m, 3H), 1.82 - 1.67 (m, 2H), 1.67 - 1.48 (m, 1 H), 1.41 - 1.10 (m, 5H), 1.05 (dt, J = 4.1 , 5.2, 2H),

1.01 - 0.85 (m, 2H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.22, 140.49, 124.82, 122.67, 121.94, 1 16.62, 110.82,

57.24, 34.37, 25.85, 24.94, 8.18, 7.73.

HRMS (ESI): m/z 256.1810 (M+H) ⁺; calc. for Ci ₆H ₂₂N ₃: 256.1814.

2 MLB133-607C N-cyclohexyl-2-(2-(methylthio)ethyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.10 - 7.94 (m, 1 H), 7.48 - 7.38 (m, 1 H), 7.06 (ddd, J = 1.3, 6.6, 9.0, 1 H), 6.72 (td, J = 1.1 , 6.8, 1 H), 3.20 - 2.78 (m, 6H), 2.18 - 2.00 (m, 3H), 1.76 (ddt, J = 6.2, 10.2, 18.4, 5H), 1.41 - 1.03 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.43, 137.54, 125.25, 123.10, 122.53, 1 16.90, 111.11 , 57.16, 34.43, 34.35, 27.81 , 25.79, 24.91 , 15.87. HRMS (ESI): m/z 290.1684 (M+H) ⁺; calc. for Ci ₆H ₂₄N ₃S: 290.1691.

3 MLB133-608A 2-sec-butyl-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 8.14 - 7.93 (m, 1 H), 7.48 (dt, J = 1.3, 9.5, 1 H), 7.04 (ddd, J = 1.2, 6.7, 8.8, 1 H), 6.71 (td, J = 1.1 , 6.9, 1 H), 3.10 - 2.63 (m, 2H), 2.12 - 1.48 (m, 9H), 1.48 - 1.06 (m, 10H), 1.06 - 0.90 (m, 2H), 0.85 (t, J = 7.3, 3H). 1 ³C NMR (50 MHz, CDCI ₃) δ 143.77, 141.75, 124.39, 123.01 , 122.71 , 1 17.13, 111.12, 57.58, 34.55, 34.51 , 33.63, 30.16, 26.09, 25.23, 25.15, 21.07, 12.87. HRMS (ESI): m/z 272.2127 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

4 MLB133-609A N-cyclohexyl-2-(5-methylisoxazol-3-yl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) 58.01 (d, J =6.9, 1H), 7.52 (d, J = 9.1, 1H), 7.18- 7.05 (m, 1H), 6.78 (td, J =0.7, 6.8, 1H), 6.63 - 6.55 (m, 1H), 4.79 - 3.86 (m, 1H), 3.17 - 2.91 (m, 1 H), 2.48 (s, 3H), 2.03 - 1.46 (m, 5H), 1.46 - 0.91 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 168.61, 159.55, 141.64, 129.39, 123.54, 123.02, 117.87, 111.94, 100.67, 56.38, 34.07, 25.70, 25.08, 12.21.

HRMS(ESI): m/z 297.1701 (M+H) ⁺; calc. for Ci ₇H ₂iN ₄O: 297.1715.

5 MLB133-616C N-butyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.92 (d, J = 6.8, 1H), 7.56-7.30 (m, 1H), 6.97 (ddd, J = 0.9, 6.7, 8.6, 1H), 6.64 (td, J = 0.6, 6.7, 1H), 3.24 - 2.97 (m, 1H), 2.90 (t, J = 6.8, 3H),

1.65 - 1.34 (m, 4H), 1.30 (d, J= 6.9, 6H), 0.87 (t, J= 7.1, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.98, 141.19, 124.52, 122.64, 122.08, 117.08, 110.96,

48.96, 32.90, 26.45, 22.80, 20.22, 13.92.

HRMS(ESI): m/z 232.1808 (M+H) ⁺; calc. for Ci ₄H ₂₂N ₃: 232.1814.

6 MLB133-623B N-cyclohexyl-2-isopropylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.02 (d, J= 6.8, 1H), 7.49 (d, J= 8.9, 1H), 7.07- 6.95 (m, 1H), 6.72 (dd, J =3.7, 9.7, 1H), 3.31 -3.01 (m, 1H), 2.85 (ddd, J = 5.2, 7.7, 10.2, 2H), 2.00 - 1.51 (m, 5H), 1.36 (d, J = 6.9, 6H), 1.22 (dt, J = 7.3, 12.7, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 144.66, 141.40, 123.06, 122.76, 122.44, 117.00, 110.94, 57.23, 34.30, 26.20, 25.85, 24.95, 22.83. HRMS(ESI): m/z 258.1963 (M+H) ⁺; calc. for Ci ₆H ₂₄N ₃: 258.1970.

7 MLB133-624B β-chloro-N-cyclohexyl^-isopropylimidazoπ ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.11 - 7.98 (m, 1 H), 7.51 - 7.34 (m, 1 H), 7.00 (ddd, J =

0.7, 2.1 , 9.5, 1 H), 3.26 - 2.99 (m, 1 H), 2.99 - 2.65 (m, 2H), 2.11 - 1.52 (m, 5H), 1.48 -

1.28 (m, 6H), 1.28 - 1.07 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 146.07, 139.73, 124.02, 123.66, 120.39, 119.45, 117.36,

57.23, 34.26, 26.28, 25.78, 24.91, 22.72. HRMS(ESI): m/z 292.1581 (M+H) ⁺; calc. for Ci ₆H ₂₃N ₃CI: 292.1581.

8 MLB133-641 A 2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.17 (dt, J = 1.0, 6.9, 1H), 7.70 (dd, J = 3.0, 6.4, 1H), 7.62 -7.52 (m, 1H), 7.52-7.29 (m, 3H), 7.16 (ddd, J= 1.1, 6.6, 9.0, 1H), 6.82 (td, J= 0.9, 6.7, 1 H), 3.29 (d, J = 6.7, 1 H), 2.68 (s, 1 H), 1.88 - 1.31 (m, 5H), 1.30 - 0.77 (m, 5H). ¹³C NMR (50 MHz, CDCI ₃) δ 141.56, 135.04, 133.98, 132.56, 129.42, 129.07, 126.86, 126.33, 123.66, 122.83, 117.52, 111.55, 56.41, 33.87, 25.67, 24.60. HRMS (ESI): m/z 326.1440 (M+H) ⁺; calc. for Ci ₉H ₂i N ₃CI: 326.1424.

9 MLB133-628A N-cyclohexyl-2-ethylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.01 (d, J =6.8, 1H), 7.45 (d, J =9.2, 1H), 7.17- 6.89 (m, 1H), 6.71 (t, J= 6.8, 1H), 2.75 (m + dd, J= 7.6, 15.1, 4H), 2.08 - 1.46 (m, 5H), 1.34 (t, J

= 7.5, 3H), 1.27 - 1.02 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.52, 140.82, 124.27, 123.22, 122.67, 117.02, 111.34,

57.42, 34.55, 26.09, 25.18, 20.74, 14.26.

HRMS(ESI): m/z 244.1809 (M+H) ⁺; calc. for Ci ₅H ₂₂N ₃: 244.1814.

10 MLB133-616B 2-isopropyl-N-(2,4,4-trimethylpentan-2-yl)imidazo[1 ,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 8.15 (d, J =6.7, 1H), 7.47 (d, J =9.0, 1H), 7.17-6.91 (m, 1 H), 6.68 (t, J = 6.7, 1 H), 3.32 - 2.96 (m, 1 H), 2.96 - 2.37 (m, 1 H), 1.35 (d, J = 6.8, 6H), 1.15 (d, J= 8.1, 6H), 1.07 (d, J= 10.9, 10H).

¹³C NMR (50 MHz, CDCI ₃) δ 146.77, 142.18, 123.36, 122.99, 121.43, 116.91, 110.57,

59.26, 56.93, 31.97, 31.82, 29.23, 26.12, 22.89.

HRMS (ESI): m/z 288.2426 (M+H) ⁺; calc. for Ci ₈H ₃₀N ₃: 288.2440.

11 MLB133-616A 2-isopropyl-N-pentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.98 (d, J= 6.8, 1H), 7.48 (d, J= 9.0, 1H), 7.04 (dd, J = 6.5, 8.5, 1 H), 6.71 (t, J = 6.9, 1 H), 3.20 - 3.05 (m, 2H), 2.96 (t, J = 7.0, 2H), 1.58 (ddd, J = 3.7, 7.9, 14.3, 2H), 1.42 - 1.10 (m, 10H), 0.90 (t, J= 7.0, 3H). 1 ³C NMR (50 MHz, CDCI ₃) δ 143.89, 141.17, 124.52, 122.69, 122.08, 117.05, 111.00, 49.25, 30.50, 29.23, 26.44, 22.79, 22.55, 14.02.

HRMS (ESI): m/z 246.1950 (M+H) ⁺; calc. for Ci ₅H ₂₄N ₃: 246.1970.

12 MLB133-640A 4-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)-2-ethoxyph enol ¹H NMR (200 MHz, CDCI ₃) δ 8.09 (d, J = 6.9, 1H), 7.74 - 7.60 (m, 1H), 7.60 - 7.37 (m, 2H), 7.20 - 7.03 (m, 1 H), 6.98 (d, J = 8.2, 1 H), 6.75 (t, J = 7.1 , 1 H), 4.35 - 4.04 (m, 3H), 3.36 - 2.68 (m, 2H), 1.95 - 1.52 (m, 5H), 1.45 (t, J = 6.9, 3H), 1.37 - 0.97 (m, 5H). ¹³C NMR (50 MHz, CDCI ₃) δ 146.08, 145.42, 141.38, 136.83, 126.87, 124.06, 123.53, 122.54, 119.92, 117.13, 114.30, 111.34, 111.17, 64.60, 56.83, 34.24, 25.79, 24.85, 15.00. HRMS (ESI): m/z 352.2025 (M+H) ⁺; calc. for C ₂IH ₂₆N ₃O ₂: 352.2025.

13 MLB133-635C 2-cyclopropyl-5,7-dimethyl-N-(naphthalen-2-yl)imidazo[1,2-a] pyridin- 3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.73 (d, J =8.7, 2H), 7.55 (d, J =8.2, 1H), 7.46 - 7.07 (m,

3H), 6.94 (dd, J = 2.3, 8.8, 1 H), 6.73 (d, J = 1.4, 1 H), 6.26 (s, 1 H), 5.58 (s, 1 H), 2.62 (s,

3H), 2.33 (s, 3H), 1.94 (ddd, J = 5.1, 8.5, 13.5, 1H), 1.16-0.97 (m, 2H), 0.87 (ddd, J =

3.8,6.3, 11.8, 2H). 1 ³C NMR (50 MHz, CDCI ₃) δ 145.76, 145.18, 144.78, 135.27, 134.89, 134.43, 129.52,

128.25, 127.63, 126.48, 126.12, 122.70, 118.67, 116.19, 115.53, 113.68, 107.06, 20.93,

18.76,7.83,7.54.

HRMS (ESI): m/z 328.1803 (M+H) ⁺; CaICfOrC ₂₂H ₂₂N ₃: 328.1814.

14 MLB133-627A N-isopropyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.14 - 8.05 (m, 1H), 7.97 (d, J = 8.9, 2H), 7.51 (dd, J = 0.5, 8.9, 1H), 7.17-7.04 (m, 1H), 6.98 (d, J =8.9, 2H), 6.74 (td, J = 0.9, 6.7, 1H), 3.84 (s, 3H), 3.40 (td, J =7.2, 13.1, 1H), 3.16 - 2.79 (m, 1H), 1.08 (d, J= 6.3, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 158.95, 141.59, 138.21, 128.31, 127.21, 123.61, 122.54, 117.22, 113.95, 111.34, 55.28, 49.12, 23.45.

HRMS (ESI): m/z 282.1602 (M+H) ⁺; calc. for Ci ₇H ₂₀N ₃O: 282.1606.

15 MLB133-640C N-cyclohexyl-5,7-dimethyl-2-propylimidazo[1,2-a]pyridin-3-am ine ¹H NMR (200 MHz, CDCI ₃) δ 7.05 (s, 1H), 6.20 (s, 1H), 2.83 (s, 3H), 2.61 (dd, J= 8.7, 16.6, 4H), 2.28 (s, 3H), 1.98-1.50 (m, 7H), 1.16 (s, 5H), 0.98 (t, J= 7.3, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.53, 140.95, 135.08, 133.70, 125.46, 115.34, 113.67, 59.57, 33.61, 29.74, 26.01, 25.17, 22.71, 20.77, 19.51, 14.33. HRMS (ESI): m/z 286.2284 (M+H) ⁺; calc. for Ci ₈H ₂₈N ₃: 286.2283. 16 DG120-034 N-butyl-N-(2-isopropylimidazo[1,2-a]pyridin-3-yl)acetamide 1H NMR (200 MHz, DMSOd ₆) δ 8.13 (d, J = 6.3, 1H), 7.55 (d, J = 9.3, 1H), 7.45-7.19 (m, 1H), 6.96 (t, J =6.7, 1H), 3.73 - 3.26 (m, 11H), 3.10 - 2.78 (m, 1H), 2.65 - 2.42 (m, 1 H), 1.73 (s, 1 H), 1.63 (s, 2H), 1.54 - 1.32 (m, 3H), 1.26 (t, J = 6.7, 6H), 0.82 (t, J = 6.9, 3H).

¹³C NMR (50 MHz, DMSOd ₆) δ 175.26, 171.14, 170.96, 146.57, 141.97, 124.82, 122.51, 118.46, 116.80, 112.58, 47.01, 30.61, 29.99, 25.61, 24.08, 22.44, 22.01, 21.82, 21.74,20.74, 19.56, 13.59.

17 MLB133-628B N,2-bis(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, DMSOd ₆) δ 8.13 - 7.79 (m, 3H), 7.55 (dd, J = 8.8, 14.7, 1H), 7.39- 7.16 (m, 1H), 7.04 - 6.83 (m, 3H), 6.76 (d, J = 8.8, 2H), 6.45 (d, J = 8.8, 2H), 3.77 (s, 3H), 3.64 (s, 3H). 1 ³C NMR (50 MHz, DMSOd ₆) δ 158.66, 152.22, 141.40, 139.19, 139.12, 137.35, 127.65, 126.18, 124.64, 122.81, 116.70, 114.97, 113.79, 113.41, 111.83, 55.19, 55.03. HRMS (ESI): m/z 346.1548 (M+H) ⁺; CaICfOrC ₂IH ₂₀N ₃O ₂: 346.1556.

18 MLB133-615B N-benzyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.99 (d, J = 6.8, 1H), 7.52 (d, J = 8.9, 1H), 7.35 (s, 5H), 7.19- 6.97 (m, 1H), 6.72 (t, J = 6.7, 1H), 4.15 (d, J= 3.7, 2H), 3.35- 3.17 (m, 1H), 3.17

-2.94(m, 1H), 1.33 (d, J= 6.9, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.54, 141.34, 139.39, 128.60, 128.22, 127.54, 123.84,

122.89, 122.05, 117.14, 111.10, 53.33, 26.49, 22.74.

HRMS (ESI): m/z 266.1637 (M+H) ⁺; calc. for Ci ₇H ₂₀N ₃: 266.1657.

19 MLB133-607B N-cyclohexyl-2-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.01 (d, J =7.3, 1H), 7.49 (d, J =9.0, 1H), 7.17- 6.92 (m, 1 H), 6.71 (t, J = 6.8, 1 H), 3.34 - 3.03 (m, 1 H), 3.02 - 2.64 (m, 2H), 2.12 - 1.82 (m, 8H), 1.82 - 1.44 (m, 5H), 1.44 - 1.00 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 142.71, 141.52, 124.07, 122.63, 122.31, 116.99, 110.83, 57.19, 37.61, 34.33, 33.53, 26.04, 25.88, 25.00. HRMS (ESI): m/z 284.2125 (M+H) ⁺; calc. for Ci ₈H ₂₆N ₃: 284.2127.

20 MLB133-615C 2-isopropyl-N-(naphthalen-2-yl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.93 - 7.79 (m, 1 H), 7.73 (d, J = 8.7, 2H), 7.69 - 7.58 (m, 1H), 7.51 (d, J = 8.1, 1H), 7.43-7.12 (m, 3H), 6.95 (dd, J = 2.4, 8.8, 1H), 6.72 (td, J = 1.1, 6.8, 1H), 6.66 (d, J = 2.2, 1H), 5.73 (s, 1H), 3.37-3.03 (m, 1H), 1.37 (d, J = 6.9, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 148.20, 143.18, 142.59, 134.74, 129.56, 128.42, 127.63, 126.54, 126.07, 124.12, 122.90, 122.44, 117.36, 116.97, 116.27, 111.68, 106.69, 26.79, 22.31. HRMS (ESI): m/z 302.1640 (M+H) ⁺; calc. for C ₂₀H ₂₀N ₃: 302.1657.

21 MLB133-608C N-cyclohexyl-2-(2,5-dimethoxytetrahydrofuran-3-yl)imidazo[1, 2- a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.09 - 7.90 (m, 1H), 7.53 - 7.37 (m, 1H), 7.15 - 6.95 (m, 1H), 6.80 - 6.64 (m, 1H), 5.40 - 4.99 (m, 2H), 3.81 - 3.62 (m, 1H), 3.44 (dd, J = 4.2, 10.4, 6H), 3.04 (dd, J = 5.3, 10.8, 1H), 2.85 (td, J = 5.5, 9.5, 1H), 2.72-2.41 (m, 1H), 2.41 -2.19 (m, 1H), 1.99 - 1.37 (m, 5H), 1.17 (dq, J= 7.5, 13.3, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 147.44, 141.52, 138.14, 137.54, 136.67, 125.76, 123.16, 122.83, 122.49, 122.25, 117.18, 117.03, 116.85, 113.69, 111.51, 111.17, 109.68, 109.13, 105.97, 105.38, 104.83, 104.50, 57.13, 57.08, 56.13, 55.74, 54.92, 42.71, 41.75, 38.71, 36.36, 34.34, 34.18, 34.11, 25.73, 25.01, 24.89, 24.85. HRMS(ESI): m/z 346.2094 (M+H) ⁺; calc. for Ci ₉H ₂₈N ₃O ₃: 346.2131.

22 MLB133-623A N-cyclohexyl-6-fluoro-2-isopropylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.96 - 7.76 (m, 1H), 7.36 (dd, J = 5.0, 9.7, 1H), 6.99 - 6.70 (m, 1H), 3.22 - 2.93 (m, 1H), 2.77 (s, 2H), 1.92 - 1.41 (m, 5H), 1.28 (d, J = 6.9, 6H), 1.22 -0.87 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 155.15, 150.48, 146.47, 138.82, 138.11, 124.36, 117.28, 117.10, 114.49, 113.97, 109.17, 108.35, 57.01, 34.11, 26.20, 25.63, 24.75, 22.61. HRMS (ESI): m/z 276.1858 (M+H) ⁺; calc. for Ci ₆H ₂₃N ₃F: 276.1876.

23 MLB133-623C N-cyclohexyl-2-isopropyl-5,7-dimethylimidazo[1,2-a]pyridin-3 -amine ¹H NMR (200 MHz, CDCI ₃) δ 7.11 (s, 1H), 6.20 (s, 1H), 3.08 (dt, J = 6.9, 13.7, 1H), 2.83 (s, 3H), 2.64 (s, 1 H), 2.26 (s, 3H), 1.89 - 1.51 (m, 5H), 1.32 (d, J = 6.9, 6H), 1.26 - 0.97 (m, 5H). ¹³C NMR (50 MHz, CDCI ₃) δ 146.49, 143.95, 135.39, 133.92, 124.12, 1 15.64, 115.61 , 114.12, 114.09, 59.82, 33.80, 26.27, 26.19, 25.45, 22.99, 21.03, 19.85. HRMS (ESI): m/z 286.2277 (M+H) ⁺; calc. TOr Ci ₈H ₂₈N ₃: 286.2283.

24 MLB133-628C 2-cyclopropyl-N-pentylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.04 - 7.91 (m, 1 H), 7.48 - 7.34 (m, 1 H), 7.14 - 6.92 (m, 1 H), 6.83 - 6.60 (m, 1 H), 3.03 (t, J = 7.1 , 3H), 1.99 (ddd, J = 5.2, 8.4, 13.5, 1 H), 1.74 - 1.49 (m, 2H), 1.49 - 1.17 (m, 4H), 1.15 - 1.00 (m, 2H), 1.00 - 0.75 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.31 , 139.89, 126.43, 122.93, 121.98, 1 16.99, 111.18, 49.36, 30.81 , 29.51 , 22.83, 14.30, 8.33, 7.81.

HRMS (ESI): m/z 244.1819 (M+H) ⁺; calc. for Ci ₅H ₂₂N ₃: 244.1814.

25 MLB133-624A 8-(benzyloxy)-N-cyclohexyl-2-isopropylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.66 (dd, J = 1.0, 6.7, 1 H), 7.62 - 7.45 (m, 2H), 7.45 - 7.20 (m, 3H), 6.65 - 6.44 (m, 1 H), 6.44 - 6.20 (m, 1 H), 5.41 (s, 2H), 3.32 - 3.05 (m, 1 H), 3.05 - 2.58 (m, 2H), 2.03 - 1.54 (m, 5H), 1.42 (d, J = 6.9, 6H), 1.35 - 1.05 (m, 5H). ¹³C NMR (50 MHz, CDCI ₃) δ 147.73, 144.20, 137.20, 128.73, 127.95, 127.19, 124.30, 116.01 , 110.72, 102.01 , 70.82, 57.54, 34.55, 26.83, 26.13, 25.23, 23.07. HRMS (ESI): m/z 364.2351 (M+H) ⁺; calc. for C ₂₃H ₃₀N ₃O: 364.2389.

26 MLB133-627C 2-(4-methoxyphenyl)-N-(naphthalen-2-yl)imidazo[1 ,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 7.98 (d, J = 8.6, 2H), 7.87 - 7.57 (m, 4H), 7.57 - 7.10 (m, 4H), 6.99 (dd, J = 2.3, 8.7, 1 H), 6.86 (d, J = 8.6, 2H), 6.78 - 6.63 (m, 2H), 5.93 (s, 1 H), 3.78 (s, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 159.65, 143.04, 142.80, 139.81 , 138.46, 135.12, 130.15, 128.87, 128.59, 127.94, 126.87, 126.47, 126.27, 125.11 , 123.31 , 122.93, 1 17.65, 116.66, 114.29, 112.25, 107.30, 55.47. HRMS (ESI): m/z 366.1577 (M+H) ⁺; calc. for C ₂₄H ₂₀N ₃O: 366.1606.

27 MLB133-629B N-benzyl-2-(4-methoxyphenyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.00 - 7.85 (m, 3H), 7.60 - 7.45 (m, 1 H), 7.40 - 7.25 (m, 5H), 7.15 - 6.95 (m, 3H), 6.75 - 6.65 (m, 1 H), 4.20 (d, 2H), 3.85 (s, 3H), 3.50 - 3.35 (m, 1 H). ¹³C NMR (50 MHz, CDCI ₃) δ 159.02, 156.38, 141.43, 139.05, 129.60, 128.58, 128.23, 128.17, 128.09, 127.53, 123.59, 122.14, 117.21, 114.04, 111.37, 55.26, 52.37. HRMS (ESI): m/z 330.1591 (M+H) ⁺; calc. for C _2IH ₂₀N ₃O: 330.1606.

28 MLB133-634A N-cyclohexyl-2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en- 2- yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.18 - 7.78 (m, 1H), 7.57 - 7.26 (m, 1H), 7.10 - 6.82 (m, 1H), 6.63 (td, J = 0.9, 6.7, 1H), 6.11 (ddd, J = 1.3, 3.2, 4.7, 1H), 3.06 (td, J= 1.3, 5.8, 1 H), 3.01 - 2.72 (m, 2H), 2.61 - 2.30 (m, 3H), 2.25 - 2.03 (m, 1 H), 1.92 - 1.44 (m, 5H), 1.32(s, 3H), 1.30-1.01 (m, 6H), 0.90 (s, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.98, 138.46, 137.13, 123.36, 122.70, 121.85, 117.41,

111.35, 57.61, 44.20, 41.16, 38.12, 34.50, 34.39, 32.50, 32.12, 26.63, 26.10, 25.21,

21.54.

HRMS (ESI): m/z 336.2413 (M+H) ⁺; calc. for C ₂₂H ₃₀N ₃: 336.2440.

29 MLB133-627B N-butyl-2-cyclopropylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.06 - 7.92 (m, 1H), 7.45 - 7.36 (m, 1H), 7.02 (ddd, J = 1.3,6.7,9.0, 1H), 6.70 (td, J= 1.1, 6.8, 1H), 3.25-2.79 (m, 3H), 1.99 (ddd, J= 5.1, 8.3, 10.0, 1H), 1.73-1.31 (m, 5H), 1.15 - 0.73 (m, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.04, 139.62, 126.15, 122.71, 121.72, 116.72, 110.95, 48.81, 32.95, 20.22, 13.95, 8.05, 7.56. HRMS(ESI): m/z 230.1646 (M+H) ⁺; calc. for Ci ₄H ₂₀N ₃: 230.1657.

30 MLB133-615A 2-isopropyl-N-(4-methoxyphenyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.87 - 7.75 (m, 1H), 7.64 - 7.50 (m, 1H), 7.23 - 7.02 (m,

1H), 6.90 - 6.61 (m, 3H), 6.56 - 6.31 (m, 2H), 5.23 (s, 1H), 3.73 (s, 3H), 3.27 - 3.01 (m,

1H), 1.32 (d, J =6.9, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 153.24, 147.91, 142.37, 139.29, 123.85, 122.40, 117.83,

117.46, 115.05, 114.08, 111.51,55.70,26.70,22.33. HRMS(ESI): m/z 282.1582 (M+H) ⁺; calc. for Ci ₇H ₂₀N ₃O: 282.1606.

31 MLB133-640B N-cyclohexyl-2-octylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.01 (d, J = 6.8, 1 H), 7.44 (d, J = 8.4, 1 H), 7.12 - 6.92 (m, 1 H), 6.70 (t, J = 6.7, 1 H), 2.98 - 2.77 (m, 2H), 2.77 - 2.58 (m, 2H), 1.95 - 1.48 (m, 7H), 1.48 - 1.00 (m, 15H), 0.98 - 0.72 (m, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.35, 139.73, 124.40, 122.69, 122.37, 1 16.85, 110.89, 57.21 , 34.33, 31.91 , 29.85, 29.67, 29.50, 29.29, 27.51 , 25.86, 24.93, 22.68, 14.09. HRMS (ESI): m/z 328.2747 (M+H) ⁺; calc. for C ₂i H ₃₄N ₃: 328.2753.

32 DG120-036 N-butyl-N-ethyl-2-isopropylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.99 (d, J = 6.8, 1 H), 7.49 (d, J = 9.0, 1 H), 7.12 - 6.98 (m, 1 H), 6.72 (t, J = 6.3, 1 H), 3.16 (dt, J = 7.0, 13.8, 1 H), 2.99 (dd, J = 6.3, 12.5, 3H), 2.88 - 2.70 (m, 1 H), 1.74 - 1.40 (m, 5H), 1.38 (d, J = 6.9, 7H), 0.95 (t, J = 7.0, 4H).

33 MLB133-608B N-cyclohexyl-2-(4-(dimethylamino)phenyl)imidazo[1 ,2-a]pyridin-3- amine 1H NMR (200 MHz, CDCI ₃) δ 8.14 - 8.04 (m, 1 H), 7.94 (d, J = 8.7, 2H), 7.54 - 7.47 (m, 1 H), 7.07 (ddd, J = 1.3, 6.6, 8.9, 1 H), 6.81 (d, J = 8.9, 1 H), 6.73 (td, J = 0.9, 6.9, 2H), 3.01 (s, 8H), 1.93 - 1.43 (m, 5H), 1.43 - 0.93 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 149.65, 141.40, 137.26, 131.84, 127.83, 123.07, 122.78, 122.41 , 116.87, 112.33, 110.95, 56.80, 40.42, 34.15, 25.79, 24.83.

34 MLB133-629A 2-(4-methoxyphenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1 ,2- a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.21 (d, J = 6.9, 1 H), 7.79 (d, J = 8.9, 2H), 7.51 (d, J = 9.0, 1 H), 7.10 (dd, J = 7.2, 8.5, 1 H), 6.97 (d, J = 8.9, 2H), 6.75 (t, J = 6.8, 1 H), 3.85 (s, 3H), 3.34 - 2.95 (m, 1 H), 1.60 (s, 2H), 1.04 (s, 9H), 0.96 (s, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 159.21 , 142.18, 140.03, 129.78, 128.35, 123.91 , 123.70, 123.01 , 117.39, 113.94, 11 1.32, 60.88, 57.35, 55.53, 32.15, 32.02, 29.26. HRMS (ESI): m/z 352.2379 (M+H) ⁺; calc. for C ₂₂H ₃₀N ₃O: 352.2389.

35 MLB133-634B (5-(3-(cyclohexylamino)imidazo[1 ,2-a]pyridin-2-yl)furan-2-yl)methanol ¹H NMR (400 MHz, CDCI ₃) δ 8.07 - 8.02 (m, 1 H), 7.49 - 7.45 (m, 1 H), 7.14 - 7.08 (m, 1 H), 6.80 - 6.71 (m, 2H), 6.33 (d, 1 H), 4.66 (s, 2H), 3.49 (br s, 1 H), 2.95 - 2.90 (m, 2H), 1.87 - 1.82 (m, 2H), 1.75 - 1.68 (m, 2H), 1.60 - 1.55 (m, 1 H), 1.35 - 1.10 (m, 5H). ¹³C NMR (101 MHz, DMSO-d ₆) δ 154.38, 148.63, 140.53, 127.56, 125.49, 123.72, 123.10, 116.47, 111.52, 108.47, 106.98, 56.25, 55.81 , 33.54, 25.36, 24.48. HRMS (ESI): m/z 312.1679 (M+H) ⁺; calc. for Ci ₈H ₂₂N ₃O ₂: 312.1712.

36 MLB133-636A 6-chloro-N-cyclohexyl-2-cyclopropylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.10 - 7.93 (m, 1 H), 7.41 - 7.27 (m, 1 H), 7.08 - 6.89 (m, 1 H), 3.19 - 2.57 (m, 2H), 2.07 - 1.84 (m, 3H), 1.84 - 1.68 (m, 2H), 1.68 - 1.45 (m, 1 H), 1.44 - 1.11 (m, 5H), 1.11 - 0.80 (m, 4H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.94, 139.49, 125.32, 123.91 , 1 19.89, 1 19.36, 116.94, 57.21 , 34.34, 25.79, 24.91 , 8.20, 7.93.

HRMS (ESI): m/z 290.1408 (M+H) ⁺; calc. for Ci ₆H ₂i N ₃CI: 290.1424.

37 MR762-137.4 2-(3,4-dimethoxyphenyl)-N-(2-morpholinoethyl)imidazo[1 ,2-a]pyridin-3- amine 1H NMR (200 MHz, CDCI ₃) δ 8.16 (d, J = 7, 1 H), 8.10 (m, 2H), 7.60 (m, 2H), 7.14-7.32 (m, 1 H), 6.93 (br t, 1 H), 4.14 (br s, 1 H), 3. 98 (s, 3H), 3. 92 (s, 3H), 3.76 (t, 4H), 3.07- 3.10 (m, 2H), 2.52-2.58 (m, 2H), 2.44 (t, 4H).

¹³C NMR (50 MHz, CDCI ₃) δ 149.6, 148.9, 138.7, 126.2, 126.0, 124.1 , 122.5, 1 19.4, 117.3, 112.0, 11 1.4, 111.3, 1 10.0, 67.0, 58.7, 56.4, 56.2, 54.0, 44.3.

38 MLB133-649A N-cyclohexyl-2-(pentan-2-yl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.93 (dt, J = 1.0, 6.8, 1 H), 7.39 (dt, J = 0.9, 9.0, 1 H), 6.93 (ddd, J = 1.3, 6.7, 9.0, 1 H), 6.59 (td, J = 1.1 , 6.7, 1 H), 3.05 - 2.60 (m, 2H), 1.91 - 1.38 (m, 6H), 1.26 (d, J = 6.9, 3H), 1.22 - 0.93 (m, 7H), 0.80 (t, J = 7.2, 3H). 1 ³C NMR (50 MHz, CDCI ₃) δ 143.69, 141.28, 123.68, 122.40, 122.21 , 1 16.71 , 110.57, 57.10, 39.10, 34.09, 31.1 1 , 25.63, 24.75, 24.68, 20.86, 13.99. HRMS (ESI): m/z 286.2251 (M+H) ⁺; calc. for Ci ₈H ₂₈N ₃: 286.2283.

39 MLB133-648B N-cyclohexyl-2-(2,4-dimethoxyphenyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.09 (dt, J = 1.0, 6.7, 1 H), 7.76 (d, J = 8.5, 1 H), 7.53 (d, J

= 9.0, 1 H), 7.08 (ddd, J = 1.3, 6.7, 9.1 , 1 H), 6.75 (td, J = 1.1 , 6.8, 1 H), 6.67 (dd, J = 2.4, 8.5, 1 H), 6.58 (d, J = 2.2, 1 H), 3.87 (s, 6H), 3.70 (s, 3H), 2.87 - 2.40 (m, 1 H), 2.01 - 1.27 (m, 4H), 1.27 - 0.75 (m, 4H). ¹³C NMR (50 MHz, CDCI ₃) δ 160.67, 156.86, 132.32, 126.71 , 123.30, 122.56, 116.96, 111.38, 105.81 , 99.31 , 67.09, 56.42, 56.12, 55.44, 34.15, 25.74, 24.83. HRMS (ESI): m/z 352.2012 (M+H) ⁺; calc. TOr C _2IH ₂₆N ₃O ₂: 352.2025.

40 MLB133-653B N-cyclohexyl-2-neopentylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.01 (dt, J = 1.0, 6.6, 1 H), 7.46 (dt, J = 1.0, 9.3, 1 H), 7.03 (ddd, J = 1.3, 6.6, 9.0, 1 H), 6.70 (td, J = 1.1 , 6.8, 1 H), 3.11 - 2.75 (m, 2H), 2.64 (s, 2H), 2.07 - 1.43 (m, 5H), 1.41 - 1.07 (m, 5H), 1.00 (s, 9H).

¹³C NMR (50 MHz, CDCI ₃) δ 140.88, 137.31 , 126.04, 122.44, 122.39, 1 16.98, 110.75, 56.84, 41.34, 34.50, 33.12, 29.85, 25.83, 24.96.

HRMS (ESI): m/z 286.2247 (M+H) ⁺; calc. for Ci ₈H ₂₈N ₃: 286.2283.

41 MLB133-655A N-cyclohexyl-2-pentylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.06 - 7.96 (m, 1 H), 7.51 - 7.35 (m, 1 H), 7.04 (ddd, J = 1.3, 6.7, 9.0, 1 H), 6.71 (td, J = 1.1 , 6.8, 1 H), 3.14 - 2.77 (m, 2H), 2.77 - 2.50 (m, 2H),

1.98 - 1.47 (m, 7H), 1.47 - 1.29 (m, 4H), 1.27 - 1.05 (m, 5H), 0.90 (t, J = 6.9, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.32, 139.65, 124.40, 122.74, 122.36, 1 16.81 , 110.92,

57.20, 34.32, 32.05, 29.35, 27.43, 25.84, 24.92, 22.57, 14.07.

HRMS (ESI): m/z 286.2270 (M+H) ⁺; calc. for Ci ₈H ₂₈N ₃: 286.2283.

42 DG 402-49706 5-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3- amine

¹ H NMR (400 MHz, CDCI ₃) δ 7.60 (d, J = 2.9, 1 H), 7.60 - 7.57 (m, 1 H), 7.54 (d, J = 1.8, 1 H), 7.52 (d, J = 1.8, 1 H), 7.50 - 7.48 (m, 1 H), 7.47 (d, J = 2.5, 1 H), 7.37 - 7.29 (m, 4H), 7.03 - 6.96 (m, 3H), 6.94 (t, J = 4.1 , 1 H), 3.28 (d, J = 6.2, 2H), 2.97 - 2.62 (m, 2H), 1.66 (d, J = 12.4, 5H), 1.59 - 1.48 (m, 4H), 1.48 - 1.35 (m, 2H), 1.16 - 0.97 (m, 7H), 0.97 - 0.75 (m, 4H).

¹³C NMR (101 MHz, CDCI ₃) δ 143.74, 138.16, 133.87, 133.32, 132.60, 129.50, 129.21 , 128.45, 126.64, 123.78, 1 18.62, 1 17.34, 1 12.21 , 58.29, 32.70, 25.73, 24.50. HRMS (ESI): m/z 404.0516 (M+H) ⁺; calc. for Ci ₉H ₂₀N ₃CIBr: 404.0529.

43 DG 402-49651 2-(2-bromophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.43 - 7.97 (m, 3H), 7.64 (td, J = 1.5, 7.7, 4H), 7.58 - 7.48 (m, 2H), 7.39 (td, J = 1.3, 7.5, 2H), 7.31 - 7.21 (m, 2H), 7.21 - 7.13 (m, 2H), 7.1 1 (dd, J = 1.3, 6.7, 1H), 6.80 (td, J = 1.1, 6.7, 2H), 3.42-3.09 (m, 2H), 2.82-2.48 (m, 2H), 1.80 -1.33(m, 12H), 1.21 -0.81 (m, 13H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.35, 136.12, 132.67, 132.50, 129.26, 127.26, 125.80, 123.51, 122.87, 122.79, 117.53, 111.46, 56.34, 33.80, 25.64, 24.51. HRMS (ESI): m/z 370.0892 (M+H) ⁺; calc. for Ci ₉H ₂iN ₃Br: 370.0919.

44 DG 402-496592-(2-chlorophenyl)-N-pentylimidazo[1,2-a]pyridin-3- amine

¹H NMR (400 MHz, CDCI ₃) δ 8.12 (dt, J = 1.2, 6.9, 1H), 7.79 - 7.61 (m, 1H), 7.55 (dt, J = 1.1, 9.1, 1H), 7.51 - 7.44 (m, 1H), 7.42 - 7.28 (m, 2H), 7.14 (ddd, J = 1.3, 6.7, 9.1, 1H), 6.82 (td, J = 1.1, 6.8, 1H), 3.30 (t, J = 6.2, 1H), 2.83 (q, J = 6.7, 2H), 1.95-1.64 (m, 1 H), 1.42 - 1.24 (m, 2H), 1.24 - 1.05 (m, 3H), 0.90 - 0.60 (m, 3H). 1 ³C NMR (101 MHz, CDCI ₃) δ 141.47, 133.93, 132.84, 132.60, 129.48, 129.14, 126.87, 123.57, 122.60, 117.69, 111.62, 48.27, 30.02, 28.93, 22.38, 13.90. HRMS(ESI): m/z 314.1414 (M+H) ⁺; calc. for Ci ₈H ₂iN ₃CI: 314.1424.

45 DG789-110 N-butyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.08 (dt, J= 1.2,6.8, 1H), 7.97 - 7.89 (m, 2H), 7.61 -7.55 (m, 1 H), 7.15 (ddd, J = 1.3, 6.7, 9.0, 1 H), 6.99 -6.94 (m, 2H), 6.82 (td, J = 1.1 , 6.8, 1 H), 3.85 (s, 4H), 3.02 (t, J= 7.1, 2H), 1.58 (dt, J = 6.9, 14.4, 2H), 1.41 (dq, J= 7.2, 14.3, 2H), 0.92 (t, J =7.3, 3H).

¹³C NMR (101 MHz, CDCI ₃) δ 159.10, 140.57, 134.37, 128.20, 125.71, 125.54, 124.57, 122.43, 116.53, 114.03, 112.06, 55.22, 47.92, 32.78, 20.18, 13.89. HRMS (ESI): m/z 296.1735 (M+H) ⁺; CaICfOrCi ₈H ₂₂N ₃O: 296.1763.

46 DG789-112 2-(4-methoxyphenyl)-N-pentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.06 (dt, J= 1.1,6.8, 1H), 7.95 - 7.89 (m, 2H), 7.56 (d, J = 9.0, 1H), 7.13 (ddd, J = 1.3, 6.7, 9.0, 1H), 7.01 - 6.94 (m, 2H), 6.80 (td, J = 1.1, 6.8, 1 H), 3.85 (s, 4H), 3.01 (t, J=I Λ, 2H), 1.58 (dd, J = 7.6, 14.8, 2H), 1.34 (ddd, J = 5.1 , 9.9, 19.4, 4H), 0.89 (t, J= 7.1, 3H). 1 ³C NMR (101 MHz, CDCI ₃) δ 159.04, 140.79, 134.74, 128.20, 126.10, 125.52, 124.24, 122.35, 116.72, 114.01, 111.85, 55.22, 48.20, 30.36, 29.17, 22.47, 13.97. HRMS(ESI): m/z 310.1906 (M+H) ⁺; calc. for Ci ₉H ₂₄N ₃O: 310.1919.

47 DG789-116 N-cyclopropyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-ami ne 48 DG 402-49760 5-chloro-2-(2-chlorophenyl)-N-cyclopentylimidazo[1 ,2-a]pyridin-3- amine

¹H NMR (400 MHz, CDCI ₃) δ 7.63 - 7.58 (m, 1 H), 7.52 - 7.46 (m, 2H), 7.38 - 7.30 (m, 2H), 7.04 (dd, J = 7.2, 9.0, 1 H), 6.78 (dd, J = 1.1 , 7.2, 1 H), 3.57 - 3.40 (m, 1 H), 3.27 (d, J = 5.7, 1 H), 1.70 - 1.46 (m, 2H), 1.46 - 1.30 (m, 4H), 1.30 - 1.14 (m, 2H). 1 ³C NMR (101 MHz, CDCI ₃) δ 143.66, 137.58, 133.63, 133.36, 132.65, 129.50, 129.27, 126.64, 126.37, 126.13, 123.65, 116.80, 1 14.02, 61.91 , 32.48, 22.98. HRMS (ESI): m/z 346.0865 (M+H) ⁺; calc. for Ci ₈H ₁₈N ₃CI ₂: 346.0878.

49 MLB133-635A N-butyl-6-chloro-2-(5-methylisoxazol-3-yl)imidazo[1 ,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 8.08 - 7.95 (m, 1 H), 7.46 (d, J = 9.6, 1 H), 7.06 (dd, J = 2.0, 9.6, 1 H), 6.56 (s, 1 H), 4.54 (t, J = 6.8, 1 H), 3.07 (dd, J = 6.9, 13.8, 2H), 2.48 (s, 3H), 1.73 - 1.50 (m, 2H), 1.50 - 1.22 (m, 2H), 0.92 (t, J = 7.2, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 168.93, 159.22, 139.76, 131.08, 124.93, 124.54, 120.57,

120.51 , 118.33, 100.50, 47.42, 32.64, 20.13, 13.85, 12.21.

HRMS (ESI): m/z 305.1180 (M+H) ⁺; calc. for Ci ₅H ₁₈N ₄CIO: 305.1 169.

50 MLB133-634C N-benzyl-6-chloro-2-(5-methylisoxazol-3-yl)imidazo[1 ,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 7.98 (dd, J = 0.9, 1.9, 1 H), 7.48 (dd, J = 0.8, 9.6, 1 H), 7.44

- 7.22 (m, 5H), 7.08 (dd, J = 2.0, 9.6, 1 H), 6.61 - 6.54 (m, 1 H), 4.80 (t, J = 6.4, 1 H),

4.25 (d, J = 6.5, 2H), 2.49 (d, J = 11.7, 3H). 1 ³C NMR (50 MHz, CDCI ₃) δ 169.36, 159.09, 140.09, 138.64, 130.45, 128.80, 128.50,

127.88, 125.78, 121.07, 120.93, 1 18.35, 100.84, 52.22, 12.49.

HRMS (ESI): m/z 339.0979 (M+H) ⁺; calc. for Ci ₈Hi ₆N ₄OCI: 339.1013.

51 MLB133-635B N-butyl-5,7-dimethyl-2-(5-methylisoxazol-3-yl)imidazo[1 ,2-a]pyridin- 3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.09 (s, 1 H), 6.56 (d, J = 0.6, 1 H), 6.25 (s, 1 H), 3.98 (t, J = 7.2, 1 H), 3.09 - 2.73 (m, 5H), 2.45 (s, 3H), 2.26 (s, 3H), 1.76 - 1.50 (m, 2H), 1.38 (dq, J = 7.1 , 13.8, 2H), 0.90 (t, J = 7.2, 3H). ¹³C NMR (50 MHz, CDCI ₃) δ 168.42, 159.50, 143.95, 135.77, 134.93, 132.46, 126.01, 116.10, 114.03, 100.75, 52.08, 31.99, 20.86, 20.19, 18.57, 13.93, 12.10. HRMS (ESI): m/z 299.1869 (M+H) ⁺; CaICfOrCi ₇H ₂₃N ₄O: 299.1872.

52 MLB133-636B N-benzyl-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.96 (d, J =6.8, 1H), 7.55-7.18 (m, 6H), 7.12- 6.97 (m, 1H), 6.77 -6.54 (m, 1H), 4.21 (s, 2H), 3.52 - 2.83 (m, 1H), 1.85 (ddd, J = 5.1, 8.3, 9.9, 1H), 1.11- 0.97 (m, 2H), 0.91 (dtd, J= 2.1, 4.9, 7.3, 2H).

¹³C NMR (50 MHz, CDCI ₃) δ 139.53, 128.72, 128.55, 128.28, 127.88, 127.46, 122.92, 121.68, 116.70, 111.00, 107.42, 53.26, 8.00, 7.57.

HRMS (ESI): m/z 264.1477 (M+H) ⁺; calc. for Ci ₇H ₁₈N ₃: 264.1501.

53 MR762-137.15 N-cyclohexyl-2-(furan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.07 (dd, J = 6.7, 1.2, 1H), 7.53 (d, J = 9.0, 1H), 7.51 (d, J =1.6, 1H), 7.15 (ddd, J = 9.0, 6.7, 1.2, 1H), 6.91 (d, J = 3.3, 1H), 6.79 (td, J = 6.7, 1.0,

1 H), 6.55 (dd, J = 3.3, 1.6, 1 H), 3.62 (br s, 1 H) 2.85-3.10 (m, 1 H), 1.50-2.00, 1.05-1.45

(m, 9H).

¹³C NMR (50 MHz, CDCI ₃) δ 149.72, 141.56, 141.37, 127.40, 125.45, 124.45, 122.81,

116.90, 111.91, 111.52, 106.98, 57.12, 34.13, 25.76, 25.01.

5410061 N-cyclohexyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amin e ¹H NMR (200 MHz, CDCI ₃) δ 8.11 (d, J = 6.8, 2H), 8.02 (d, J =8.6, 2H), 7.16-7.08 (m, 1H), 7.02-6.98 (d, J = 8.6, 2H), 6.80-6.73 (m, 1 H), 3.87 (s, 3H), 1.80-1.59 (br m, 10H).

¹³C NMR (50 MHz, CDCI ₃) δ 158.3, 141.6, 138.3, 137.1, 128.6, 127.3, 124.3, 123.9, 118.5, 117.3, 116.2, 57.1, 55.5, 34.4, 26.0, 25.1.

55 MR762-137.82-(furan-2-yl)-N-(2-morpholinoethyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.07 (dd, J = 6.4, 1.2, 1H), 7.51 (d, J = 8.0, 1H), 7.45 (d, J = 0.8, 1 H), 7.11 (ddd, J = 8.0, 6.4, 1.2, 1 H), 6.89 (d, J = 3.2, 1 H), 6.78 (td, J = 6.4, 0.8, 1H), 6.53 (dd, J = 3.2, 1.2, 1H), 4.34 (br s, 1H), 3.76 (m 4H), 3.13 (t, J = 6.0, 2H), 2.61 (t, J= 6.4, 2H), 2.50 (br s, 4H).

¹³C NMR (50 MHz, CDCI ₃) δ 150.3, 141.7, 141.3, 126.9, 126.7, 123.9, 122.4, 117.3, 111.6, 111.5, 106.3,67.0,58.2,53.5,44.3. 56 MR762-137.11 N-cyclohexyl-2-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-3- amine ¹H NMR (200 MHz, CDCI ₃) δ 8.01 (d, J = 6.8, 1H), 7.71 (d, J = 1.8, 1H), 7.60-7.48 (m, 2H), 7.12 -6.94 (m, 1H), 6.90, (d, J = 8.4, 1H), 3.97 (s, 3H), 3.91 (s, 3H), 3.20 - 2.81 (m, 2H), 1.83-1.21 (brm, 10H).

¹³C NMR (50 MHz, CDCI ₃) 149.3, 148.7, 141.6, 136.7, 127.6, 124.4, 123.9, 122.8, 119.7, 117.3, 111.7, 111.4, 110.9,67.3, 57.0,56.2,56.1, 34.5,26.0,25.1.

57 MLB133-639A 4-(3-(cyclohexylamino)imidazo[1 ,2-a]pyridin-2-yl)-2,6- dimethoxyphenol

¹H NMR (200 MHz, DMSOd ₆) δ 8.49 - 8.22 (m, 2H), 7.45 (d, J = 8.8, 1 H), 7.21 - 7.06 (m, 1H), 6.86 (t, J = 6.7, 1H), 4.87 - 4.59 (m, 1H), 3.85 (s, 6H), 3.07 - 2.81 (m, 1H), 1.86 - 1.43 (m, 5H), 1.43 - 0.92 (m, 5H).

¹³C NMR (50 MHz, DMSOd ₆) δ 147.76, 140.11, 135.09, 134.79, 124.95, 124.41, 123.44, 123.03, 116.24, 110.93, 104.05, 56.18, 55.86, 33.58, 25.44, 24.40. HRMS (ESI): m/z 368.1946 (M+H) ⁺; calc. for C ₂i H ₂₆N ₃O ₃: 368.1974.

58 MLB133-639C 2-(4-(benzyloxy)benzyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.10 (d, J =6.8, 1H), 8.01 (d, J =8.8, 2H), 7.59 - 7.27 (m, 7H), 7.13 -7.00 (m, 2H), 6.76 (t, J = 6.8, 1H), 5.13 (s, 2H), 2.98 (m, 1H), 1.75 (m, 5H),

1.47- 0.97 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 158.10, 141.42, 136.97, 136.56, 129.52, 128.45, 128.28,

127.83, 127.43, 124.05, 123.51, 122.52, 117.07, 114.82, 111.27, 69.99, 56.77, 34.13,

25.73, 24.79. HRMS (ESI): m/z 412.2364 (M+H) ⁺; calc. for C ₂₇H ₃₀N ₃O: 412.2389.

59 MLB133-639B 2-(3-(cyclohexylamino)imidazo[1 ,2-a]pyridin-2-yl)phenol

¹H NMR (200 MHz, DMSO-d ₆ + CD ₃OD) δ 8.36 (d, J= 6.8, 1H), 8.17 (dd, J= 1.7, 8.1, 1H), 7.54 (d, 1H), 7.40- 7.15 (m, 2H), 7.10 -6.85 (m, 3H), 3.05-2.81 (m, 1H), 1.99- 1.44(m, 5H), 1.44-1.01 (m, 5H).

¹³C NMR (50 MHz, DMSO-d ₆ + CD ₃OD) δ 156.77, 141.58, 135.94, 129.75, 129.14, 125.78, 125.08, 123.89, 119.89, 117.86, 116.87, 113.01, 57.65, 34.24, 26.43, 25.54. HRMS (ESI): m/z 308.1767 (M+H) ⁺; CaICfOrCi ₉H ₂₂N ₃O: 308.1763. 60 MLB133-649C N-cyclohexyl-2-(pentan-3-yl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.05 (dt, J = 1.0, 6.8, 1 H), 7.58 - 7.38 (m, 1 H), 7.03 (ddd, J = 1.3, 6.6, 9.0, 1 H), 6.70 (td, J = 1.1 , 6.7, 1 H), 3.20 - 2.72 (m, 1 H), 2.72 - 2.42 (m, 1 H), 1.99 - 1.44 (m, 9H), 1.41 - 1.01 (m, 6H), 0.80 (t, J = 7.4, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 142.04, 141.60, 125.60, 122.61 , 122.45, 1 16.96, 110.69, 57.56, 40.98, 34.25, 28.31 , 25.86, 24.92, 12.62. HRMS (ESI): m/z 286.2281 (M+H) ⁺; calc. for Ci ₈H ₂₈N ₃: 286.2283.

61 MLB133-648A N-cyclohexyl-2-(4-nitrophenyl)imidazo[1 ,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 8.49 - 8.21 (m, 4H), 8.07 (dt, J = 1.0, 6.9, 1 H), 7.55 (d, J =

8.3, 1 H), 7.18 (ddd, J = 1.3, 6.7, 9.1 , 1 H), 6.83 (td, J = 1.0, 6.8, 1 H), 3.28 - 2.79 (m,

2H), 2.04 - 1.47 (m, 5H), 1.47 - 0.97 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 146.55, 142.06, 141.13, 134.43, 127.26, 126.47, 124.83,

123.80, 122.65, 117.89, 112.23, 57.12, 34.36, 25.66, 24.87. HRMS (ESI): m/z 337.1670 (M+H) ⁺; calc. for C19H21 N ₄O ₂: 337.1665.

62 MLB133-648C N-cyclohexyl-2-isobutylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.08 - 7.95 (m, 1 H), 7.50 - 7.36 (m, 1 H), 7.03 (ddd, J =

1.2, 6.7, 9.0, 1 H), 6.70 (td, J = 0.9, 6.7, 1 H), 3.00 - 2.69 (m, 2H), 2.58 (d, J = 7.1 , 2H), 2.20 (dt, J = 6.8, 13.4, 1 H), 2.04 - 1.49 (m, 5H), 1.38 - 1.07 (m, 5H), 0.95 (d, J = 6.6,

6H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.29, 138.72, 125.17, 122.65, 122.38, 1 16.83, 110.81 ,

57.21 , 36.67, 34.34, 28.88, 25.83, 24.92, 22.74.

HRMS (ESI): m/z 272.2105 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

63 MLB133-649B 4-(3-(cyclohexylamino)imidazo[1 ,2-a]pyridin-2-yl)phenol

¹H NMR (200 MHz, DMSOd ₆) δ 9.41 (s, 1 H), 8.26 (d, J = 6.9, 1 H), 8.03 (d, J = 8.6, 2H), 7.41 (d, J = 8.9, 1 H), 7.28 - 7.01 (m, 1 H), 6.83 (t, J = 7.3, 3H), 4.60 (d, J = 5.5, 1 H), 3.45 - 3.38 (m, 1 H), 3.00 - 2.65 (m, 1 H), 2.01 - 1.40 (m, 5H), 1.40 - 0.85 (m, 5H). ¹³C NMR (50 MHz, DMSOd ₆) δ 154.73, 138.53, 133.82, 126.11 , 123.79, 122.44, 121.29, 121.20, 114.42, 1 13.20, 109.01 , 54.45, 31.83, 23.77, 22.78. HRMS (ESI): m/z 308.1754 (M+H) ⁺; CaIC fOr Ci ₉H ₂₂N ₃O: 308.1763.

64 MLB133-650A 2-tert-butyl-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.08 (dt, J = 1.0, 6.9, 1 H), 7.47 (d, J = 9.0, 1 H), 7.04 (ddd, J = 1.3, 6.6, 8.9, 1H), 6.69 (td, J = 0.9, 6.7, 1H), 3.17-2.71 (m, 2H), 2.06- 1.51 (m, 6H), 1.47 (s, 9H), 1.40 - 1.02 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 140.10, 138.20, 123.62, 122.89, 116.56, 111.17, 109.72, 58.68, 34.13, 33.19, 30.66, 25.82, 25.05.

HRMS (ESI): m/z 272.2102 (M+H) ⁺; CaICfOrCi ₇H ₂₆N ₃: 272.2127.

65 MLB133-650B N-(4-(3,4-dichlorophenoxy)butyl)-2-(furan-2-yl)imidazo[1 ,2-a]pyridin- 3-amine 1H NMR (200 MHz, CDCI ₃) δ 7.88 (d, J= 6.9, 1H), 7.50 - 7.25 (m, 2H), 7.15 (d, J= 8.9, 1 H), 6.98 (ddd, J = 1.0, 6.7, 8.2, 1 H), 6.83 (d, J = 2.9, 1 H), 6.79 - 6.72 (m, 1 H), 6.70 - 6.50 (m, 2H), 6.47 - 6.24 (m, 1H), 3.79 (dd, J = 7.6, 13.5, 2H), 3.59 (d, J = 6.1, 1H), 2.98 (dd, J = 6.4, 12.9, 2H), 1.88 - 1.31 (m, 4H). 1 ³C NMR (50 MHz, CDCI ₃) δ 157.76, 150.15, 141.52, 141.32, 132.52, 130.38, 129.19, 127.45, 126.16, 123.57, 122.13, 117.09, 116.14, 115.54, 114.26, 111.51, 106.26, 68.07, 48.10,26.99,26.46. HRMS (ESI): m/z 416.0902 (M+H) ⁺; CaICfOrC ₂IH ₂₀N ₃O ₂CI ₂: 416.0933.

66 MLB133-650C N-(4-(3,4-dichlorophenoxy)butyl)-2-isopropylimidazo[1 ,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 7.88 (dt, J= 1.0, 6.8, 1H), 7.37 (br dt, J= 9.0, 1H), 7.16 (d, J = 8.9, 1 H), 6.95 (dd, J = 1.2, 6.7, 1 H), 6.90 (dd, J = 1.3, 6.8, 1 H), 6.85 (d, J = 2.9, 1 H), 6.71 -6.49(m, 1H), 3.82 (t, J= 6.0, 2H), 3.20 - 2.99 (m, 1H), 2.92 (d, J= 6.1, 3H), 1.89 _ 1.44 (m, 4H), 1.27 (d, J= 6.9, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 157.76, 144.16, 141.06, 132.51, 129.16, 128.99, 123.96, 122.57, 121.87, 120.40, 116.86, 115.52, 114.26, 110.86, 68.08, 48.68, 27.25, 26.51, 26.25, 22.64. HRMS (ESI): m/z 392.1259 (M+H) ⁺; calc for C ₂₀H ₂₄N ₃OCI ₂: 392.1296.

67 MLB133-650D N-(4-chlorobenzyl)-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.96 (d, J =6.8, 2H), 7.52 (d, J =9.0, 2H), 7.18- 6.99 (m, 2H), 6.73 (t, J = 6.7, 2H), 4.03 (s, 2H), 3.39 - 3.07 (m, 1 H), 3.07 - 2.81 (m, 1 H), 1.23 (d, J= 6.9, 6H). ¹³C NMR (101 MHz, CDCI ₃) δ 144.68, 141.38, 137.86, 133.42, 129.58, 128.75, 123.52,

123.24, 122.00, 117.17, 111.34, 52.60, 26.43, 22.69.

HRMS(ESI): m/z 300.1241 (M+H) ⁺; calc. for Ci ₇H ₁₉N ₃CI: 300.1268.

68 MLB133-653A 2-(5-chlorofuran-2-yl)-N-cyclohexylimidazo[1,2-a]pyridin-3-a mine

¹H NMR (200 MHz, CDCI ₃) δ 7.98 (dt, J = 1.1, 6.8, 1H), 7.47-7.34 (m, 1H), 7.04 (ddd, J = 1.3, 6.7, 9.1 , 1 H), 6.76 (d, J = 3.4, 1 H), 6.69 (td, J = 1.0, 6.8, 1 H), 6.21 (d, J = 3.4, 1 H), 3.42 (d, J = 6.6, 1 H), 3.07 - 2.73 (m, 1 H), 2.01 - 1.41 (m, 5H), 1.41 - 0.99 (m, 5H). ¹³C NMR (50 MHz, CDCI ₃) δ 149.97, 141.83, 135.16, 127.34, 125.70, 124.15, 122.79, 117.22, 111.66, 108.25, 108.04, 57.38, 34.18, 25.76, 24.95.

HRMS(ESI): m/z 316.1195 (M+H) ⁺; calc. for Ci ₇H ₁₉N ₃OCI: 316.1217.

69 MLB133-653C N-cyclohexyl-2-(5-ethylthiophen-2-yl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI3) δ 8.07 (dt, J = 1.1, 6.9, 1H), 7.50 (d, J= 9.0, 1H), 7.41 (d, J = 3.6, 1H), 7.10 (ddd, J= 1.3, 6.6, 9.0, 1H), 6.92-6.79 (m, 1H), 6.79-6.66 (m, 1H),

3.27 - 2.97 (m, 2H), 2.90 (dd, J = 7.6, 15.1, 2H), 2.09-1.51 (m, 5H), 1.36 (t, J = 7.5,

4H), 1.30 - 1.00 (m, 4H).

¹³C NMR (50 MHz, CDCI ₃) δ 147.81, 140.51, 125.43, 125.06, 124.05, 123.45, 122.97,

116.09, 112.42, 57.03, 34.26, 25.74, 24.92, 23.51, 15.86. HRMS (ESI): m/z 326.1695 (M+H) ⁺; calc. for Ci ₉H ₂₄N ₃S: 326.1691.

70 MLB133-654C 4-(3-(cyclohexylamino)imidazo[1 ,2-a]pyridin-2-yl)-2-methoxyphenol ¹H NMR (200 MHz, DMSOd ₆) δ 8.98 (s, 1H), 8.30 (d, 1H), 7.80 (s, 1H), 7.65 (d, 1H), 7.45 (d, 1H), 7.15 (t, 1H), 6.95 - 6.75 (m, 2H), 4.70 (d, 1H), 3.85 (s, 3H), 3.00 -2.80 (m, 1H), 1.85 -0.95 (m, 10H).

¹³C NMR (50 MHz, DMSOd ₆) δ 147.31, 145.71, 140.23, 135.31, 126.14, 124.33,

123.28, 123.08, 119.41, 116.30, 115.33, 110.96, 110.62, 56.21, 55.49, 33.55, 25.44,

24.43.

HRMS (ESI): m/z 338.1872 (M+H) ⁺; CaICfOrC ₂₀H ₂₄N ₃O ₂: 338.1869.

71 MLB133-654A 5-(3-(cyclohexylamino)imidazo[1 ,2-a]pyridin-2-yl)-2-methoxyphenol ¹H NMR (200 MHz, CDCI ₃- CD ₃OD) δ 8.04 (d, 1 H), 7.50 - 7.25 (m, 3H), 7.15 - 7.00 (m, 1 H), 6.85 (d, 1 H), 6.75 - 6.65 (m, 1 H), 3.83 (s, 3H), 3.75 - 3.45 (m, 1 H), 2.95 - 2.75 (m, 1H), 1.85- 0.90 (m, 10H). ¹³C NMR (50 MHz, CDCI ₃ - DMSO-d ₆) δ 147.18, 145.94, 140.35, 134.58, 125.63, 125.20, 124.38, 122.77, 118.47, 115.46, 113.79, 112.21, 111.22, 56.50, 55.59, 33.78, 25.46,24.61.

HRMS (ESI): m/z 338.1873 (M+H) ⁺; CaICfOrC ₂₀H ₂₄N ₃O ₂: 338.1869.

72 MLB133-654B N-cyclohexyl-2-(3-methylthiophen-2-yl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI3) δ 8.12 (d, J = 6.9, 1H), 7.56 (d, J = 8.9, 1H), 7.28 (d, J = 4.3, 1H), 7.20 - 7.06 (m, 1H), 6.96 (d, J = 5.1, 1H), 6.80 (td, J = 0.7, 6.8, 1H), 3.46 - 3.04 (m, 1H), 3.04 - 2.76 (m, 1H), 2.47 (s, 3H), 2.02 - 1.43 (m, 5H), 1.36 - 0.94 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.26, 135.92, 131.79, 130.54, 129.38, 125.91, 124.12, 123.58, 122.66, 117.33, 111.51, 56.75, 33.92, 25.73, 24.74, 15.24. HRMS (ESI): m/z 312.1534 (M+H) ⁺; calc. for Ci ₈H ₂₂N ₃S: 312.1534.

73 DG 402-49647 N-cyclohexyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyri din-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 8.22 (d, J =8.2, 2H), 8.08 (dt, J= 1.0, 6.0, 1H), 7.68 (d, J = 8.3, 2H), 7.60-7.45 (m, 1H), 7.15 (ddd, J= 1.2, 6.7, 9.0, 1H), 6.80 (td, J= 1.0, 6.7, 1 H), 3.29 - 2.67 (m, 2H), 1.96 - 1.42 (m, 5H), 1.42 - 0.91 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.75, 138.01, 135.14, 128.46, 126.91, 125.59, 125.31 (dd, J= 3.8, 7.6), 124.45, 124.34, 122.64, 117.57, 111.84, 56.94, 34.22, 25.65, 24.81. HRMS (ESI): m/z 360.1683 (M+H) ⁺; calc. for C ₂₀H _2I N ₃F ₃: 360.1688.

74 DG 402-49648 2-(6-chloro-2-fluoro-3-methylphenyl)-N-cyclohexylimidazo[1,2 - a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.14 (d, J =6.9, 1H), 7.57 (d, J= 9.1, 1H), 7.26 - 7.05 (m,

3H), 6.82 (dd, J = 3.8, 9.7, 1 H), 3.02 (s, 1 H), 2.82 - 2.60 (m, 1 H), 2.31 (d, J = 2.1 , 3H),

1.75 (d, J = 11.7, 2H), 1.65 - 1.54 (m, 2H), 1.54 - 1.40 (m, 1 H), 1.22 - 0.87 (m, 5H).

¹³C NMR (101 MHz, CDCI ₃) δ 160.71, 158.24, 141.67, 132.21, 131.55, 131.49, 127.21, 124.60, 124.56, 123.95, 123.77, 123.62, 122.76, 117.77, 111.56, 56.31, 33.76, 25.60,

24.61, 14.54.

HRMS (ESI): m/z 358.1481 (M+H) ⁺; calc. for C ₂₀H ₂₂N ₃CIF: 358.1486. 75 DG 402-49649 2-(4-chloro-3-fluorophenyl)-N-cyclohexylimidazo[1,2-a]pyridi n-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 8.06 (d, J = 6.8, 1H), 7.97 (dd, J = 1.9, 10.9, 1H), 7.91 - 7.77 (m, 1H), 7.52 (d, J =9.3, 1H), 7.44 (t, J = 8.1, 1H), 7.23-7.08 (m, 1H), 6.81 (td, J =0.8,6.8, 1H), 3.16 -2.79 (m, 2H), 1.99 - 1.42 (m, 6H), 1.42 - 0.90 (m, 7H).

¹³C NMR (50 MHz, CDCI ₃) δ 160.56, 155.65, 141.62, 130.43, 125.07, 124.50, 123.14, 123.07, 122.58, 117.46, 115.11, 114.66, 111.96, 56.91,34.24,25.65,24.83. HRMS (ESI): m/z 344.1323 (M+H) ⁺; calc. for Ci ₉H ₂₀N ₃FCI: 344.1330.

76 DG 402-496502-(3-bromophenyl)-N-cyclohexylimidazo[1,2-a]pyridin -3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.35 - 8.21 (m, 1H), 8.15 - 8.04 (m, 1H), 8.04 - 7.90 (m, 1H), 7.61 -7.47(m, 1H), 7.43 (ddd, J= 1.1, 1.9, 7.9, 1H), 7.29 (dd, J = 5.4, 10.3, 1H), 7.13 (ddd, J= 1.3,6.7,9.0, 1H), 6.79 (td, J= 1.1,6.8, 1H), 3.29 - 2.66 (m, 2H), 1.69(M, 6H), 1.41 -0.74(m, 7H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.62, 136.60, 131.01, 130.03, 129.98, 129.89, 125.34, 124.13, 122.69, 122.63, 117.46, 111.72, 56.97, 34.25, 25.70, 24.82. HRMS(ESI): m/z 370.0911 (M+H) ⁺; calc. for C ₁9H ₂₁ N ₃Br: 370.0919.

77 DG 402-496532-(4-bromophenyl)-N-cyclohexylimidazo[1,2-a]pyridin -3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.09 - 8.00 (m, 1H), 7.94 (d, J = 8.6, 2H), 7.58 - 7.43 (m,

3H), 7.10 (ddd, J = 1.3, 6.7, 9.0, 1H), 6.75 (td, J = 1.1, 6.8, 1H), 3.01 (s, 2H), 1.93 -

1.39 (m, 5H), 1.16 (s, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.57, 135.62, 133.46, 131.43, 128.49, 124.83, 123.98,

122.55, 121.09, 117.33, 111.58, 56.77, 34.32, 25.66, 24.76. HRMS (ESI): m/z 370.0926 (M+H) ⁺; calc. for Ci ₉H ₂iN ₃Br: 370.0919.

78 DG 402-496552-(2-chlorophenyl)-N-(pentan-2-yl)imidazo[1,2-a]pyr idin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.26 - 8.03 (m, 1H), 7.77 - 7.61 (m, 1H), 7.61 - 7.50 (m, 1H), 7.50-7.41 (m, 1H), 7.41 -7.21 (m, 2H), 7.12 (ddd, J= 1.1, 6.7, 8.9, 1H), 6.78 (td, J= 0.7, 6.7, 1 H), 3.33 - 3.03 (m, 1 H), 3.03 - 2.74 (m, 1 H), 1.44 - 0.99 (m, 4H), 0.84 (d, J= 6.3, 3H), 0.75 (dd, J= 6.2, 7.4, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.51, 134.02, 132.58, 132.41, 129.29, 129.23, 128.97, 126.73, 123.51, 123.37, 122.63, 117.43, 111.41, 53.14, 39.54, 20.79, 18.85, 13.93. HRMS(ESI): m/z 314.1402 (M+H) ⁺; calc. for Ci ₈H ₂iN ₃CI: 314.1424. 79 DG 402-496572-isopropyl-N-(pentan-2-yl)imidazo[1,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 8.12 - 7.92 (m, 1 H), 7.59 - 7.40 (m, 1 H), 7.05 (ddd, J = 1.2, 6.7, 8.9, 1H), 6.71 (dd, J =0.8, 13.6, 1H), 3.25-2.98 (m, 2H), 2.95 - 2.56 (m, 1H), 1.63 - 1.40 (m, 3H), 1.37 (dd, J = 2.9, 6.9, 6H), 1.06 (d, J = 6.3, 2H), 0.93 (dd, J = 5.5, 8.4, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.92, 141.51, 123.23, 122.69, 122.36, 117.07, 110.92, 53.66, 40.03, 26.24, 22.73, 21.01, 19.45, 14.24. HRMS (ESI): m/z 246.1967 (M+H) ⁺; calc. for Ci ₅H ₂₄N ₃: 246.1970.

80 DG 402-49667 6,8-dichloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]py ridin-3- amine

¹H NMR (400 MHz, CDCI ₃) 58.13 (d, J = 1.8, 1H), 7.75-7.64 (m, 1H), 7.52 - 7.42 (m, 2H), 7.42 - 7.29 (m, 4H), 7.24 (d, J = 1.8, 1 H), 3.29 (s, 1 H), 2.66 (dd, J = 7.7, 11.3, 1 H), 2.01 -0.74 (m, 29H).

¹³C NMR (101 MHz, CDCI ₃) δ 137.08, 133.13, 132.79, 132.67, 129.64, 129.60, 129.40, 128.19, 127.05, 123.79, 123.63, 119.68, 119.25, 67.07, 56.46, 33.79, 25.53, 24.49. HRMS (ESI): m/z 394.0643 (M+H) ⁺; calc. for Ci ₉H ₁₉N ₃CI ₃: 394.0645.

81 DG 402-49663 2-(2-chlorophenyl)-N-cyclohexyl-6-fluoroimidazo[1,2-a]pyridi n-3- amine

¹H NMR (400 MHz, CDCI ₃) 58.13 (d, J = 1.8, 1H), 7.71 -7.67 (m, 1H), 7.48 - 7.44 (m,

1 H), 7.38 - 7.33 (m, 2H), 7.24 (d, J = 1.8, 1 H), 3.33 (d, J = 29.8, 1 H), 2.66 (s, 1 H), 1.77

- 1.60 (m, 3H), 1.51 (dd, J= 14.4, 43.3, 2H), 1.12- 0.97 (m, 5H). 1 ³C NMR (101 MHz, CDCI ₃) δ 154.41, 152.06, 139.17, 136.70, 133.59, 132.41, 129.50,

129.33, 127.59, 127.57, 127.01, 118.12, 118.03, 115.96, 115.70, 109.51, 109.10, 56.28,

33.81,25.55,24.55.

HRMS (ESI): m/z 344.1299 (M+H) ⁺; calc. for Ci ₉H ₂₀N ₃CIF: 344.1330.

82 DG 402-49665 6-chloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridi n-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 8.25 - 8.11 (m, 1H), 7.75-7.56 (m, 1H), 7.55-7.39 (m, 2H), 7.39-7.25 (m, 2H), 7.10 (ddd, J= 1.2, 1.9, 9.5, 1H), 3.27 (d, J= 6.8, 1H), 2.80- 2.46 (m, 1 H), 1.82 - 1.34 (m, 5H), 1.23 - 0.76 (m, 5H). ¹³C NMR (50 MHz, CDCI ₃) δ 139.84, 136.39, 133.58, 132.56, 132.38, 129.44, 129.27, 126.88, 126.72, 124.94, 120.67, 120.08, 117.96, 56.36, 33.79, 25.58, 24.52. HRMS (ESI): m/z 360.1019 (M+H) ⁺; CaICfOrCi ₉H ₂₀N ₃CI ₂: 360.1034.

83 DG 402-49672 N-cyclopentyl-2-(2,4-dichlorophenyl)imidazo[1,2-a]pyridin-3- amine ¹H NMR (200 MHz, CDCI ₃) δ 8.16 (dt, J = 1.2, 7.3, 1H), 7.63 (d, J = 8.3, 1H), 7.58 - 7.41 (m, 2H), 7.42 -7.30 (m, 1H), 7.15 (ddd, J = 1.3,6.7,9.1, 1H), 6.82 (t, J = 6.8, 1H), 3.33 (dt, J =5.7, 11.0, 1H), 3.14 (d, J = 6.2, 1H), 1.75- 1.37 (m, 6H), 1.37- 1.04 (m, 2H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.65, 134.28, 134.07, 133.27, 133.21, 132.75, 129.24, 127.27, 127.06, 123.97, 122.72, 117.53, 111.72, 59.36, 33.27, 23.29. HRMS (ESI): m/z 346.0889 (M+H) ⁺; calc. for Ci ₈H ₁₈N ₃CI ₂: 346.0878.

84 DG 402-496732-(4-bromophenyl)-N-cyclopentylimidazo[1,2-a]pyridi n-3-amine ¹H NMR (400 MHz, CDCI ₃) δ 8.05 (dt, J = 1.1,6.9, 1H), 8.00 - 7.89 (m, 2H), 7.61 -7.44 (m, 3H), 7.12 (ddd, J= 1.3, 6.7, 9.0, 1H), 6.76 (td, J= 1.1, 6.8, 1H), 3.72-3.47 (m, 1H), 2.99 (d, J = 3.9, 1 H), 1.83 - 1.60 (m, 4H), 1.60 - 1.49 (m, 2H), 1.49 - 1.35 (m, 2H). ¹³C NMR (101 MHz, CDCI ₃) δ 141.63, 135.83, 133.49, 131.45, 128.62, 125.49, 124.10, 122.47, 121.18, 117.44, 111.67, 59.06, 33.46, 23.57. HRMS (ESI): m/z 356.0727 (M+H) ⁺; calc. for Ci ₈H ₁₉N ₃Br: 356.0762.

85 DG 402-496782-(3-bromophenyl)-N-cyclopentylimidazo[1,2-a]pyridi n-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.31 - 8.28 (m, 1H), 8.09 (d, J = 6.8, 1H), 8.04 - 7.97 (m, 1H), 7.52 (dt, J = 3.5, 7.8, 1H), 7.43 (ddd, J = 0.9, 1.9, 7.9, 1H), 7.32 - 7.24 (m, 1H), 7.17-7.11 (m, 1H), 6.79 (td, J = 0.8, 6.8, 1H), 3.66 (t, J = 10.3, 1H), 3.01 (s, 1H), 1.88 - 1.65 (m, 4H), 1.65 - 1.53 (m, 2H), 1.53 - 1.39 (m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.71, 136.63, 135.41, 130.13, 130.10, 130.06, 129.94, 125.80, 125.52, 124.26, 122.70, 122.55, 117.61, 111.82, 59.24, 33.56, 23.61. HRMS (ESI): m/z 356.0774 (M+H) ⁺; calc. for Ci ₈Hi ₉N ₃Br: 356.0762.

86 DG 402-49679 2-(4-chloro-3-fluorophenyl)-N-cyclopentylimidazo[1,2-a]pyrid in-3- amine

¹H NMR (400 MHz, CDCI ₃) δ 8.05 (d, J= 6.7, 1H), 7.96 (d, J= 10.9, 1H), 7.85 (d, J = 8.4, 1 H), 7.51 (d, J = 9.0, 1 H), 7.42 (t, J = 8.0, 1 H), 7.20 - 7.07 (m, 1 H), 6.79 (t, J = 6.7, 1 H), 3.88 - 3.40 (m, 1 H), 2.97 (d, J = 3.8, 1 H), 1.87 - 1.62 (m, 4H), 1.62 - 1.52 (m, 2H), 1.52 - 1.35 (m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 159.39, 156.93, 141.73, 135.29, 135.22, 134.97, 130.38, 125.70, 124.44, 123.27, 123.23, 122.49, 119.51, 119.33, 117.62, 115.13, 114.90, 111.92,59.12,33.54,23.61.

HRMS (ESI): m/z 330.1173 (M+H) ⁺; calc. for Ci ₈H ₁₈N ₃FCI: 330.1173.

87 DG 402-49680 2-(6-chloro-2-fluoro-3-methylphenyl)-N-cyclopentylimidazo[1, 2- a]pyridin-3-amine 1H NMR (400 MHz, CDCI ₃) 58.23 -8.08 (m, 1H), 7.56 (ddd, J = 1.0, 1.9,9.1, 1H), 7.23 - 7.06 (m, 3H), 6.87 - 6.72 (m, 1 H), 3.54 - 3.27 (m, 1 H), 2.96 (d, J = 6.4, 1 H), 2.39 - 2.21 (m, 3H), 1.72-1.51 (m, 4H), 1.51 - 1.37 (m, 2H), 1.37 - 1.16 (m, 2H). 1 ³C NMR (101 MHz, CDCI ₃) δ 160.78, 158.31, 141.64, 132.36, 132.32, 131.52, 131.45, 129.80, 127.90, 124.58, 124.54, 123.93, 123.74, 123.57, 122.61, 122.11, 121.92, 117.83, 111.52, 59.33, 33.16, 23.24, 14.48, 14.44.

HRMS (ESI): m/z 344.1328 (M+H) ⁺; calc. for Ci ₉H ₂₀N ₃FCI: 344.1330.

88 DG 402-49681 N-cyclopentyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyr idin-3- amine 1H NMR (400 MHz, CDCI ₃) δ 8.21 (d, J = 8.0, 2H), 8.07 (d, J = 6.9, 1H), 7.67 (d, J= 7.9, 2H), 7.53 (d, J= 9.1, 1H), 7.15 (dd, J = 7.2, 8.5, 1H), 6.79 (t, J = 6.8, 1H), 3.75-3.50 (m, J = 9.6, 1 H), 3.04 (d, J = 3.2, 1 H), 1.87 - 1.62 (m, 4H), 1.62 - 1.51 (m, 2H), 1.50 - 1.36 (m, 2H). 1 ³C NMR (101 MHz, CDCI ₃) δ 141.81, 138.09, 138.08, 135.39, 129.07, 128.75, 127.10, 126.25, 125.69, 125.33, 125.29, 125.25, 125.22, 124.40, 122.56, 117.66, 111.89, 59.20, 33.51,23.57. HRMS (ESI): m/z 346.1525 (M+H) ⁺; CaICfOrCi ₉Hi ₉N ₃F ₃: 346.1531.

89 DG 402-49686 N-cyclohexyl-2-(2,4-dichlorophenyl)imidazo[1,2-a]pyridin-3-a mine ¹H NMR (400 MHz, CDCI ₃) δ 8.14 (ddd, J =0.9, 1.6,6.9, 1H), 7.64 - 7.60 (m, 1H), 7.56 -7.52(m, 1H), 7.51 - 7.48 (m, 1H), 7.38 - 7.33 (m, 1H), 7.19- 7.12 (m, 1H), 6.81 (tt, J = 1.8, 9.2, 1H), 3.19 (d, J = 6.0, 1H), 2.67 (dd, J= 3.8, 9.0, 1H), 1.65 (t, J= 11.2, 2H), 1.59 (dd, J= 4.6, 8.9, 2H), 1.53- 1.42 (m, 1H), 1.17 - 0.92 (m, 6H). ¹³C NMR (101 MHz, CDCI ₃) δ 141.75, 134.27, 134.14, 133.34, 133.14, 132.80, 129.29, 127.33, 126.44, 123.93, 122.89, 117.57, 111.70, 56.43, 33.89, 25.62, 24.58. HRMS (ESI): m/z 360.1025 (M+H) ⁺; CaICfOrCi ₉H ₂₀N ₃CI ₂: 360.1034.

90 DG 402-49688 N-(1-adamantyl)-2-(2-chlorophenyl)imidazo[1,2-a]pyridin-3-am ine

¹H NMR (400 MHz, CDCI ₃) δ 8.39 - 8.34 (m, 1H), 7.75 - 7.68 (m, 1H), 7.52 (ddd, J = 5.0, 6.0, 11.0, 1H), 7.48 -7.43 (m, 1H), 7.40 - 7.29 (m, 2H), 7.17-7.11 (m, 1H), 6.82- 6.75 (m, 1H), 3.28-3.11 (m, 1H), 1.95 - 1.83 (m, 3H), 1.52 (d, J = 12.2, 3H), 1.42 (t, J = 10.7, 9H). 1 ³C NMR (101 MHz, CDCI ₃) δ 142.21, 137.82, 134.92, 132.85, 132.46, 129.45, 129.04, 126.94, 124.04, 123.94, 123.77, 117.36, 111.21, 55.83, 43.49, 36.17, 29.61. HRMS(ESI): m/z 378.1731 (M+H) ⁺; calc. for C ₂₃H ₂₅N ₃CI: 378.1737.

91 DG 402-49690 N-(1-adamantyl)-2-(5-methylisoxazol-3-yl)imidazo[1,2-a]pyrid in-3- amine

¹H NMR (400 MHz, CDCI ₃) δ 8.30 (dt, J = 7.3, 15.7, 1H), 7.50 (dt, J = 6.1, 12.2, 1H), 7.16- 7.07 (m, 1H), 6.80 - 6.70 (m, 1H), 6.63 - 6.56 (m, 1H), 4.17 - 3.98 (m, 1H), 2.60 - 2.40 (m, 3H), 1.98 (d, J = 20.6, 2H), 1.82 - 1.70 (m, 5H), 1.62 - 1.47 (m, 5H). 1 ³C NMR (101 MHz, CDCI ₃) δ 168.66, 159.46, 142.39, 128.08, 126.54, 124.33, 124.13, 117.50, 111.52, 101.16, 57.60, 43.42, 36.20, 29.78, 12.20.

HRMS (ESI): m/z 349.2013 (M+H) ⁺; calc. for C ₂i H ₂₅N ₄O: 349.2028.

92 DG 402-49683 N-cyclopentyl-2-(2,6-difluorophenyl)imidazo[1,2-a]pyridin-3- amine ¹H NMR (400 MHz, CDCI ₃) δ 8.19 - 8.13 (m, 1H), 7.56 (t, J = 10.7, 1H), 7.41 - 7.29 (m, 1H), 7.19-7.11 (m, 1H), 7.06 - 6.97 (m, 2H), 6.87 - 6.75 (m, 1H), 3.48 - 3.32 (m, 1H), 3.07 (d, J = 6.1 , 1 H), 1.73 - 1.53 (m, 4H), 1.53 - 1.38 (m, 2H), 1.38 - 1.24 (m, 2H). ¹³C NMR (101 MHz, CDCI ₃) δ 162.09, 162.02, 159.61, 159.54, 142.02, 129.83, 129.72, 129.62, 128.46, 126.59, 123.80, 122.64, 117.88, 111.75, 111.69, 111.66, 111.56, 111.49, 59.42,33.23,23.24. HRMS(ESI): m/z 314.1462 (Mn-H) ⁺SCaICfOrCi ₈H ₁₈N ₃F ₂: 314.1469.

93 DG 402-49694 N-(1-adamantyl)-2-(3-methylthiophen-2-yl)imidazo[1,2-a]pyrid in-3- amine ¹H NMR (400 MHz, CDCI ₃) δ 8.28 (dt, J = 1.2,7.0, 1H), 7.51 (dt, J = 1.1, 9.1, 1H), 7.27 (d, J = 4.8, 1H), 7.12 (ddd, J = 1.3, 6.6, 9.0, 1H), 6.93 (d, J= 5.1, 1H), 6.76 (td, J= 1.1, 6.8, 1H), 3.01 (s, 1H), 2.36(s, 3H), 1.94 (s, 3H), 1.67- 1.34 (m, 12H). 1 ³C NMR (101 MHz, CDCI ₃) δ 142.08, 135.20, 131.03, 130.16, 127.25, 124.57, 123.81, 123.58, 120.05, 117.31, 111.16, 56.25, 43.44, 36.19, 29.68, 15.17. HRMS (ESI): m/z 364.1836 (M+H) ⁺; CaICfOrC ₂₂H ₂₆N ₃S: 364.1847.

94 DG 402-49700 2-(2-chlorophenyl)-N-(1-adamantyl)imidazo[2,1-a]isoquinolin- 3- amine 1H NMR (400 MHz, CDCI ₃) δ 8.66 (ddd, J = 6.1, 6.6, 12.7, 1H), 8.18 (d, J = 7.4, 1H), 7.78 (dd, J = 1.8, 7.6, 1H), 7.73 - 7.67 (m, 1H), 7.62 - 7.50 (m, 2H), 7.48 - 7.44 (m, 1 H), 7.42 - 7.36 (m, 1 H), 7.36 - 7.29 (m, 1 H), 7.05 (t, J = 5.0, 1 H), 3.23 (s, 1 H), 1.90 (s, 3H), 1.66 (d, J = 2.9, 3H), 1.51 (s, 2H), 1.46 (d, J = 2.4, 8H). 1 ³C NMR (101 MHz, CDCI ₃) δ 139.64, 135.61, 134.88, 132.95, 132.50, 129.60, 129.57, 129.39, 128.86, 128.28, 127.80, 127.76, 127.00, 126.76, 123.88, 122.79, 121.30, 111.80, 55.63, 43.50, 36.12, 29.58. HRMS (ESI): m/z 428.1896 (M+H) ⁺; CaICfOrC ₂₇H ₂₇N ₃CI: 428.1894.

95 DG 402-49702 6-bromo-2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1,2- a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.71 - 7.55 (m, 1H), 7.55 - 7.42 (m, 1H), 7.42 - 7.29 (m, 2H), 7.25 (d, J = 4.3, 2H), 3.18 (s, 3H), 2.55 (s, 1H), 1.53 (d, J= 17.9, 5H), 1.16-0.65 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 142.05, 138.18, 137.93, 135.11, 134.05, 132.69, 132.49, 129.40, 129.23, 128.26, 126.90, 116.25, 109.91, 58.69, 33.04, 25.68, 24.68, 17.94. HRMS (ESI): m/z 418.0676 (M+H) ⁺; calc for C ₂₀H ₂₂N ₃CIBr: 418.0686.

96 DG 402-49704 2-(2-chlorophenyl)-3-(cyclohexylamino)imidazo[1,2-a]pyridine -6- carbonitrile 1H NMR (400 MHz, CDCI ₃) δ 8.65 - 8.55 (m, 1 H), 7.68 - 7.63 (m, 1 H), 7.61 (ddd, J = 0.9, 3.4, 9.3, 1 H), 7.53 - 7.46 (m, 1 H), 7.43 - 7.32 (m, 2H), 7.27 - 7.19 (m, 1 H), 3.53 - 3.13 (m, 1H), 2.86 -2.55 (m, 1H), 1.60 (dd, J= 23.5, 47.2, 5H), 1.20 - 0.95 (m, 5H). ¹³C NMR (101 MHz, CDCI ₃) δ 140.47, 137.48, 132.83, 132.57, 132.30, 129.76, 129.62, 129.36, 127.41, 127.07, 123.24, 118.50, 117.05, 97.81, 56.58, 33.76, 25.44, 24.45. HRMS (ESI): m/z 351.1361 (M+H) ⁺; calc. for C ₂₀H ₂₀N ₄CI: 351.1376.

97 DG 402-49754 2-(2-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]quinolin-1 -amine

¹H NMR (400 MHz, CDCI ₃) δ 9.44 (dt, J = 5.7, 11.5, 1 H), 7.74 (dt, J = 4.5, 9.0, 1 H), 7.71 - 7.65 (m, 1 H), 7.62 - 7.55 (m, 1 H), 7.52 - 7.47 (m, 1 H), 7.46 - 7.40 (m, 3H), 7.39 - 7.36 (m, 1 H), 7.36 - 7.33 (m, 1 H), 3.60 - 3.39 (m, 1 H), 2.86 - 2.67 (m, 1 H), 1.74 (dd, J = 12.6, 18.3, 2H), 1.60 - 1.36 (m, 3H), 1.11 - 0.86 (m, 5H). 1 ³C NMR (101 MHz, CDCI ₃) δ 140.68, 134.79, 132.65, 131.29, 129.57, 129.44, 129.34,

129.05, 128.43, 127.66, 127.36, 127.01 , 125.69, 124.42, 124.33, 117.52, 1 17.1 1 , 56.59, 33.10, 25.58, 24.62.

HRMS (ESI): m/z 376.1576 (M+H) ⁺; calc. for C ₂₃H ₂₃N ₃CI: 376.1581.

98 DG 402-49708 6-bromo-2-(2-chlorophenyl)-N-cyclohexyl-8-methylimidazo[1 ,2- a]pyridin-3-amine 1H NMR (400 MHz, CDCI ₃) δ 8.22 - 8.08 (m, 1 H), 7.74 - 7.59 (m, 1 H), 7.53 - 7.41 (m, 1 H), 7.41 - 7.27 (m, 2H), 7.03 (dd, J = 1.1 , 1.8, 1 H), 3.22 (d, J = 6.9, 1 H), 2.72 - 2.61 (m, 1 H), 2.60 (s, 3H), 1.73 - 1.40 (m, 6H), 1.17 - 0.82 (m, 6H).

¹³C NMR (101 MHz, CDCI ₃) δ 140.39, 135.51 , 133.81 , 132.77, 132.61 , 129.42, 129.25, 128.52, 126.99, 126.84, 125.82, 120.85, 106.62, 56.38, 33.80, 25.59, 24.53, 16.43. HRMS (ESI): m/z 418.0676 (M+H) ⁺; CaIC fOr C ₂₀H ₂₂N ₃CIBr: 418.0686.

99 DG 402-49710 6-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3- amine

¹H NMR (400 MHz, CDCI3) δ 8.33 - 8.21 (m, 1 H), 7.70 - 7.56 (m, 1 H), 7.52 - 7.45 (m, 1 H), 7.45 - 7.40 (m, 1 H), 7.40 - 7.29 (m, 2H), 7.20 (dd, J = 1.9, 9.5, 1 H), 3.25 (d, J = 6.9, 1 H), 2.66 (dd, J = 3.4, 6.5, 1 H), 1.75 - 1.62 (m, 2H), 1.61 - 1.52 (m, 2H), 1.52 - 1.39 (m, 1 H), 1.18 - 0.86 (m, 5H). 1 ³C NMR (101 MHz, CDCI3) δ 139.99, 136.23, 133.61 , 132.62, 132.46, 129.52, 129.35,

127.06, 126.97, 126.62, 123.02, 1 18.30, 106.65, 56.41 , 33.81 , 25.58, 24.53. HRMS (ESI): m/z 404.0512 (M+H) ⁺; calc. for Ci ₉H ₂₀N ₃CIBr: 404.0529.

100 DG 402-49692 N-(1-adamantyl)-2-octylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.30 - 8.09 (m, 1 H), 7.43 (dt, J = 1.1 , 9.0, 1 H), 7.04 (ddd, J = 1.3, 6.6, 9.0, 1 H), 6.69 (td, J = 1.1 , 6.8, 1 H), 2.77 - 2.70 (m, 2H), 2.05 (d, J = 8.4, 3H), 1.79 (dt, J = 7.7, 15.7, 2H), 1.72 (d, J = 2.5, 6H), 1.64 (d, J= 12.3, 3H), 1.57 (d, J = 12.3, 3H), 1.45- 1.17 (m, 11H), 0.87 (t, J= 6.9, 3H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.92, 141.67, 123.26, 122.92, 122.06, 116.66, 110.52, 55.48, 44.01, 36.27, 31.87, 29.91, 29.73, 29.54, 29.46, 29.25, 27.98, 22.65, 14.06. HRMS (ESI): m/z 380.3053 (M+H) ⁺; calc. for C ₂₅H ₃₈N ₃: 380.3066.

101 DG 402-49675 2-(2-bromophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) 58.17 (dt, J= 1.1, 6.9, 1H), 7.64 (ddd, J= 1.3, 4.4, 9.5, 2H), 7.59-7.49 (m, 1H), 7.40 (ddd, J= 0.6, 1.2, 7.5, 1H), 7.27-7.20 (m, 1H), 7.18-7.08 (m, 1H), 6.80 (ddd, J= 0.6, 1.0,6.7, 1H), 3.46 - 3.27 (m, 1H), 3.21 (d, J =6.4, 1H), 1.68 - 1.48 (m, 4H), 1.48 - 1.35 (m, 2H), 1.35 - 1.13 (m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.31, 136.72, 136.11, 132.69, 132.53, 129.32, 127.29, 126.48, 123.65, 122.88, 122.68, 117.54, 111.55, 59.30, 33.16, 23.19. HRMS (ESI): m/z 356.0768 (M+H) ⁺; calc. for Ci ₈Hi ₉N ₃Br: 356.0762.

102 DG 402-49682 N-cyclopentyl-2-(2,6-dichlorophenyl)imidazo[1,2-a]pyridin-3- amine ¹H NMR (400 MHz, CDCI ₃) 58.16 (d, J =6.9, 1H), 7.67-7.49 (m, 1H), 7.49 - 7.36 (m, 2H), 7.33-7.21 (m, 1H), 7.19-7.03 (m, 1H), 6.81 (dd, J = 3.6, 10.3, 1H), 3.50-3.32 (m, 1 H), 2.84 (d, J = 6.0, 1 H), 1.72 - 1.53 (m, 4H), 1.53 - 1.40 (m, 2H), 1.40 - 1.27 (m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.46, 136.35, 132.97, 129.88, 128.01, 127.38, 123.61,

122.70, 117.89, 111.60, 59.41, 33.29, 23.34.

HRMS (ESI): m/z 346.0877 (M+H) ⁺; calc. for Ci ₈Hi ₈N ₃CI ₂: 346.0878.

103 DG 402-49696 N-(1-adamantyl)-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.18 (dt, J= 1.2, 6.9, 1H), 7.39 (dt, J= 1.1, 9.0, 1H), 7.03 (ddt, J= 1.2, 6.7, 9.0, 1H), 6.68 (td, J= 1.1, 6.8, 1H), 2.77 (s, 1H), 2.19- 1.93 (m, 4H), 1.77 (d, J = 2.5, 6H), 1.61 (q, J= 12.2, 6H), 1.13 - 1.03 (m, 2H), 0.99 - 0.91 (m, 2H). ¹³C NMR (101 MHz, CDCI ₃) δ 142.47, 141.73, 122.88, 122.75, 122.49, 116.39, 110.46, 55.60, 43.98, 36.27, 29.73, 8.87, 8.18.

HRMS (ESI): m/z 308.2128 (M+H) ⁺; CaICfOrC ₂₀H ₂₆N ₃: 308.2127.

104 DG402-49748 5-chloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3- amine ¹H NMR (400 MHz, CDCI ₃) δ 7.63 - 7.56 (m, 1 H), 7.49 (dddd, J = 1.3, 1.8, 4.5, 5.0, 2H), 7.39 - 7.30 (m, 2H), 7.08 - 6.99 (m, 1 H), 6.80 - 6.73 (m, 1 H), 3.31 (d, J = 6.8, 1 H), 2.81 (s, 1 H), 1.67 (d, J = 12.5, 2H), 1.52 (s, 2H), 1.45 (s, 1 H), 1.06 (t, J = 10.4, 3H), 0.89 (d, J = 10.1 , 2H). 1 ³C NMR (101 MHz, CDCI ₃) δ 143.62, 137.52, 133.65, 133.24, 132.59, 129.49, 129.25, 128.24, 126.67, 125.99, 123.55, 1 16.77, 1 14.06, 58.58, 32.78, 25.67, 24.50. HRMS (ESI): m/z 360.1014 (M+H) ⁺; CaIC fOr Ci ₉H ₂₀N ₃CI ₂: 360.1034.

105 DG 402-49758 2-(2-bromophenyl)-N-cyclohexylimidazo[2,1-a]isoquinolin-3-am ine ¹H NMR (400 MHz, CDCI ₃) δ 8.66 (d, J = 8.0, 1 H), 7.99 (dd, J = 1.3, 7.3, 1 H), 7.75 -

7.63 (m, 3H), 7.63 - 7.56 (m, 1 H), 7.56 - 7.48 (m, 1 H), 7.42 (ddd, J = 1.4, 4.5, 7.6, 1 H), 7.32 - 7.18 (m, 1 H), 7.06 (d, J = 7.3, 1 H), 3.29 (d, J = 6.9, 1 H), 2.70 (s, 1 H), 1.79 - 1.64 (m, 2H), 1.57 (s, 2H), 1.51 - 1.42 (m, 1 H), 1.17 - 0.97 (m, 4H), 0.95 - 0.75 (m, 1 H). ¹³C NMR (101 MHz, CDCI ₃) δ 138.83, 136.1 1 , 134.54, 132.88, 132.55, 129.39, 129.25, 127.85, 127.74, 127.62, 127.50, 126.87, 123.95, 123.13, 122.73, 120.43, 1 12.28, 56.86, 33.75, 25.62, 24.53. HRMS (ESI): m/z 420.1063 (M+H) ⁺; calc. for C ₂₃H ₂₃N ₃Br: 420.1075.

106 SG389-832C N-cyclohexyl-2-(2,5-dichlorophenyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.15 (d, J = 7.1 , 1 H), 7.69 (d, J = 2.5, 1 H), 7.52 (d, J = 9.1 , 1 H), 7.46 - 7.06 (m, 5H), 6.84 (d, J = 6.7, 1 H), 2.25 - 2.07 (m, 5H), 1.83 - 1.43 (m, 12H), 1.41 - 0.96 (m, 25H), 0.96 - 0.73 (m, 16H).

¹³C NMR (50 MHz, CDCI ₃) δ 138.21 , 132.79, 132.26, 130.77, 130.64, 130.58, 129.45, 129.10, 128.52, 124.09, 122.92, 1 17.54, 1 11.80, 56.52, 33.93, 31.59, 24.61. HRMS (ESI): m/z 360.1037 (M+H) ⁺; CaIC fOr Ci ₉H ₂₀N ₃CI ₂: 360.1034.

107 SG389-834H N-cyclopentyl-2-(2,4-difluorophenyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.15 (dt, J = 1.0, 6.9, 1 H), 7.60 (d, J = 8.3, 1 H), 7.51 (dt, J = 0.9, 9.0, 1 H), 7.48 (d, J = 2.1 , 1 H), 7.34 - 7.30 (m, 1 H), 7.14 (ddd, J = 1.2, 6.7, 9.0, 1 H), 6.79 (td, J = 0.9, 6.7, 1 H), 3.39 - 3.27 (m, 1 H), 3.20 (s, 1 H), 1.68 - 1.48 (m, 4H), 1.48 - 1.34 (m, 2H), 1.34 - 1.17 (m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.30, 134.09, 133.50, 133.02, 132.97, 132.30, 129.01 , 127.05, 126.87, 123.99, 122.53, 117.06, 1 11.62, 58.99, 32.94, 22.99. HRMS (ESI): m/z 314.1473 (M+H) ⁺; calc for Ci ₈Hi ₈N ₃F ₂: 314.1469. 108 SG389-832A 2-(3-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.21 -8.10(m, 1H), 8.07 (d, J = 6.9, 1H), 8.01 - 7.82 (m, 1 H), 7.52 (d, J = 9.1 , 1 H), 7.43 - 7.20 (m, 2H), 7.20 - 7.02 (m, 1 H), 6.78 (t, J = 6.8, 1 H), 3.20 - 2.75 (m, 2H), 1.99 - 1.42 (m, 6H), 1.42 - 0.92 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.55, 136.30, 135.18, 134.39, 129.55, 127.06, 127.02, 125.17, 124.86, 124.08, 122.60, 117.40, 111.66, 56.90, 34.19, 25.67, 24.78. HRMS (ESI): m/z 326.1423 (M+H) ⁺; calc. for Ci ₉H ₂i N ₃CI: 326.1424.

109 SG389-832D N-cyclohexyl^-^β-dichlorophenyOimidazoπ^-alpyridin-S-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.15 (d, J =6.9, 1H), 7.56 (d, J = 9.1, 1H), 7.48 - 7.35 (m, 2H), 7.28 (dd, J = 6.6, 8.8, 1 H), 7.21 - 7.02 (m, 1 H), 6.81 (td, J = 0.7, 6.7, 1 H), 3.03 - 2.55 (m, 2H), 1.93 - 1.40 (m, 8H), 1.39 - 0.96 (m, 14H), 0.96 - 0.65 (m, 8H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.53, 136.31, 133.06, 129.85, 128.90, 128.00, 126.72, 123.56, 122.85, 117.83, 111.55, 56.58, 33.84, 25.69, 24.60.

HRMS (ESI): m/z 360.1042 (M+H) ⁺; CaICfOrCi ₉H ₂₀N ₃CI ₂: 360.1034.

110 SG389-832E N-cyclohexyl-2-(2,6-difluorophenyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.13 (dt, J = 1.2,6.9, 1H), 7.57 (dt, J = 1.1, 9.1, 1H), 7.34 (tt, J = 6.4, 8.3, 1H), 7.14 (ddd, J= 1.3, 6.6, 9.1, 1H), 7.03 (t, J= 8.1, 2H), 6.80 (td, J =

1.1,6.8, 1H), 3.12(s, 1H), 2.71 (s, 1H), 1.84 - 1.66 (m, 2H), 1.66 - 1.54 (m, 2H), 1.54-

1.42 (m, 1H), 1.21 - 0.92 (m, 6H).

¹³C NMR (101 MHz, CDCI ₃) δ 161.92, 161.85, 159.44, 159.37, 141.97, 129.75, 129.64,

129.54, 127.74, 126.45, 123.75, 122.71, 117.69, 111.72, 111.59, 111.46, 56.40, 33.87, 25.53, 24.64.

HRMS (ESI): m/z 328.1630 (M+H) ⁺; CaICfOrCi ₉H ₂₀N ₃F ₂: 328.1625.

111 DG 402-49756 N-cyclohexyl-2-(2-fluorophenyl)imidazo[2,1-a]isoquinolin-3-a mine ¹H NMR (400 MHz, CDCI ₃) δ 8.66 (ddd, J =0.7, 1.3, 2.6, 1H), 8.04-7.94 (m, 2H), 7.70 (dd, J = 0.9, 8.0, 1 H), 7.66 - 7.57 (m, 1 H), 7.54 (ddd, J = 1.4, 7.2, 7.7, 1 H), 7.40 - 7.27 (m, 2H), 7.20-7.12 (m, 1H), 7.05 (d, J= 7.2, 1H), 3.49 (s, 1H), 2.72 (s, 1H), 1.78 (s, 2H), 1.62 (s, 2H), 1.51 (s, 1H), 1.10 (d, J= 7.7, 5H). ¹³C NMR (101 MHz, CDCI ₃) δ 160.62, 158.21, 139.52, 131.50, 129.37, 128.88, 128.79, 127.86, 127.82, 126.90, 124.76, 123.94, 122.75, 120.52, 119.88, 115.68, 115.45, 112.25, 57.26, 33.96, 25.63, 24.83.

HRMS (ESI): m/z 360.1857 (M+H) ⁺; CaICfOrC ₂₃H ₂₃N ₃F: 360.1876.

112 SG389-816A N-(2-chloro-6-methylphenyl)-2-cyclopropylimidazo[1 ,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 7.91 (d, J = 6.8, 1H), 7.46 (d, J = 9.0, 1H), 7.25 (d, J= 6.8, 1H), 7.17- 7.00 (m, 1H), 6.93 (d, J= 7.1, 1H), 6.77 (dd, J= 6.7, 14.2, 2H), 5.87 (s, 1H), 2.85(s, 1H), 1.79 - 1.49 (m, 3H), 1.16 - 0.85 (m, 2H), 0.85 - 0.54 (m, 2H).

¹³C NMR (50 MHz, CDCI ₃) δ 142.56, 141.29, 139.91, 130.63, 128.32, 127.15, 123.48, 123.38, 121.58, 121.34, 120.13, 116.68, 111.66, 18.16, 7.62, 7.17. HRMS (ESI): m/z 298.1123 (M+H) ⁺; calc. for Ci ₇H ₁₇N ₃CI: 298.111.

113 SG389-832B N-cyclohexyl-2-(2-fluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.15 (d, J = 6.9, 1H), 7.92 (td, J = 2.3, 7.6, 1H), 7.54 (d, J = 9.1, 1H), 7.22 (m, 4H), 6.79 (t, J= 6.7, 1H), 3.45 (t, J = 7.8, 1H), 2.91 -2.46 (m, 1H), 1.88 - 1.34 (m, 5H), 1.21 - 0.83 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.74, 131.58, 131.49, 129.15, 128.98, 124.60, 124.54, 123.65, 122.88, 117.38, 115.76, 115.29, 111.44, 56.65, 34.01, 25.66, 24.79. HRMS (ESI): m/z 310.1724 (M+H) ⁺; calc. for Ci ₉H ₂iN ₃F: 310.1720.

114 SG389-834A 2-(3-chlorophenyl)-N-cyclopentylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.13 (t, J= 1.9, 1H), 8.04 (dt, J= 1.1, 6.9, 1H), 7.94 (dt, J = 1.4, 7.7, 1H), 7.50 (dt, J= 1.0, 9.0, 1H), 7.33 (t, J = 7.8, 1H), 7.25 (ddd, J= 1.1, 2.1, 8.0, 1H), 7.15-7.07 (m, 1H), 6.75 (td, J= 1.1, 6.8, 1H), 3.70-3.52 (m, 1H), 3.03 (d, J = 3.2, 1 H), 1.84 - 1.61 (m, 4H), 1.59 - 1.49 (m, 2H), 1.49 - 1.32 (m, 2H). 1 ³C NMR (101 MHz, CDCI ₃) δ 141.48, 136.13, 135.21, 134.29, 129.53, 127.09, 126.98, 125.72, 124.90, 124.28, 122.49, 117.31, 111.74, 59.01, 33.40, 23.49. HRMS (ESI): m/z 312.1273 (M+H) ⁺; calc. for Ci ₈H ₁₉N ₃CI: 312.1268.

115 SG389-834C 2-(4-chlorophenyl)-N-cyclopentylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.08 (dt, J= 1.2, 6.9, 1H), 8.04-7.98 (m, 2H), 7.52 (dt, J = 1.0, 9.1, 1H), 7.42 - 7.37 (m, 2H), 7.14 (ddd, J= 1.3, 6.7, 9.0, 1H), 6.79 (td, J = 1.1, 6.8, 1H), 3.62 (s, 1H), 3.02 (s, 1H), 1.83 - 1.62 (m, 4H), 1.62 - 1.50 (m, 2H), 1.50 - 1.38 (m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.49, 135.58, 133.05, 132.74, 128.58, 128.33, 125.47, 124.38, 122.54, 117.29, 111.85, 59.05, 33.45, 23.56. HRMS (ESI): m/z 312.1273 (M+H) ⁺; calc. for Ci ₈H ₁₉N ₃CI: 312.1268.

116 CW23836 2-(2-chlorophenyl)-3-(cyclohexylamino)imidazo[1 ,2-a]pyridine-5- carbonitrile

¹H NMR (400 MHz, CDCI ₃) δ 7.80 (dd, J =0.9, 9.0, 1H), 7.62 (dt, J = 3.1, 5.4, 1H), 7.54 - 7.47 (m, 1H), 7.45 - 7.34 (m, 3H), 7.17 (dd, J = 7.1, 8.9, 1H), 3.33 (d, J = 7.1, 1H),

2.79 (d, J = 3.3, 1 H), 1.73 (d, J = 10.2, 2H), 1.55 (d, J = 3.8, 3H), 1.44 (d, J = 13.8, 1 H),

1.04 (dd, J = 10.2, 19.7, 5H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.06, 138.44, 133.09, 132.37, 129.80, 129.66, 128.09,

127.08, 124.31, 124.30, 122.94, 121.90, 113.97, 108.02, 57.24, 32.67, 25.60, 24.54.

117SG389-812 N-(3-chlorophenyl)-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.78 (d, J =6.8, 1H), 7.56 (d, J =9.0, 1H), 7.25-7.11 (m,

1 H), 7.06 (t, J = 8.0, 1 H), 6.86 - 6.61 (m, 2H), 6.51 (t, J = 2.0, 1 H), 6.37 (dd, J = 2.2,

8.1, 1H), 5.81 (s, 1H), 3.27 -2.83 (m, 1H), 1.29 (d, J= 6.9, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 148.27, 146.94, 142.60, 135.34, 130.53, 124.27, 122.19,

119.44, 117.33, 116.27, 113.16, 111.83, 111.28,26.71,22.22.

HRMS (ESI): m/z 286.1118 (M+H) ⁺; calc. for Ci ₆H ₁₇N ₃CI: 286.111.

118 SG389-834B 2-(2-chlorophenyl)-N-cyclopentylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.23 - 8.13 (m, 1H), 7.76 - 7.62 (m, 1H), 7.62 - 7.42 (m, 2H), 7.42 -7.23 (m, 2H), 7.15 (ddd, J= 1.3, 6.8, 9.1, 1H), 6.81 (td, J= 1.0, 6.8, 1H), 3.34 (dt, J= 5.0, 10.2, 1H), 3.21 (d, J= 6.4, 1H), 2.21 - 1.82 (m, 1H), 1.72- 1.04 (m, 7H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.55, 134.01, 132.66, 132.57, 129.44, 129.11, 127.00, 126.87, 123.74, 122.71, 117.56, 111.60, 59.42, 33.24, 23.28.

HRMS(ESI): m/z 312.1270 (M+H) ⁺; calc. for Ci ₈Hi ₉N ₃CI: 312.1268.

119 SG389-816B N-(2-chloro-6-methylphenyl)-2-isopropylimidazo[1 ,2-a]pyridin-3- amine ¹H NMR (200 MHz, CDCI ₃) δ 8.02 (dd, J = 1.1, 6.8, 1H), 7.56 (d, J = 9.0, 1H), 7.26 (d, J = 7.8, 1H), 7.20 - 6.99 (m, 1H), 6.93 (d, J= 6.7, 1H), 6.88 - 6.63 (m, 2H), 5.77 (s, 1H), 2.85 (dt, J= 6.9, 13.8, 1H), 1.61 (s, 3H), 1.23 (dd, J= 7.3, 14.5, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 146.67, 141.52, 140.23, 130.59, 128.13, 127.27, 123.44, 123.32, 122.01, 121.38, 118.58, 117.02, 111.81, 26.15, 21.73 (br), 18.03. HRMS (ESI): m/z 300.1271 (M+H) ⁺; calc. for Ci ₇H ₁₉N ₃CI: 300.1268.

120SG389-816C N-(2-chloro-6-methylphenyl)-2-ethylimidazo[1,2-a]pyridin-3-a mine ¹H NMR (200 MHz, CDCI ₃) δ 8.14 - 7.91 (m, 1H), 7.52 (d, J = 9.0, 1H), 7.26 (d, J= 6.1, 1H), 7.21 -7.03(m, 1H), 6.94 (d, J =7.1, 1H), 6.81 (t, J = 7.6, 2H), 5.76 (s, 1H), 2.50 (dd, J= 7.6, 15.1, 2H), 1.62 (s, 3H), 1.14 (t, J= 7.6, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 142.86, 141.53, 140.10, 130.61, 128.49, 127.27, 123.58, 123.46, 122.01, 121.58, 119.58, 117.02, 111.86,20.34, 18.11, 12.84. HRMS (ESI): m/z 286.1117 (M+H) ⁺; calc. for Ci ₆Hi ₇N ₃CI: 286.1111.

121 SG389-834G N-cyclopentyl^-^S-dichlorophenyOimidazoπ^-alpyridin-S-amine ¹H NMR (400 MHz, CDCI ₃) δ 8.16 (dt, J= 1.2, 6.9, 1H), 7.67 (d, J = 2.6, 1H), 7.49 (dt, J = 1.1, 9.1, 1H), 7.39 (d, J= 8.6, 1H), 7.29 (dd, J = 2.6, 8.6, 1H), 7.17 (ddd, J= 1.3, 6.7, 9.1, 1H), 6.82 (tt, J =3.2, 6.5, 1H), 3.37 (d, J= 25.1, 1H), 3.18 (s, 1H), 2.02 - 1.88 (m, 1H), 1.70 - 1.50 (m, 4H), 1.50 - 1.37 (m, 2H), 1.37 - 1.19 (m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.47, 135.21, 132.65, 132.04, 130.71, 130.45, 129.10, 128.93, 128.48, 124.32, 122.70, 117.19, 111.87, 59.24, 33.10, 23.10. HRMS (ESI): m/z 346.0878 (M+H) ⁺; calc. for Ci ₈Hi ₈N ₃CI ₂: 346.0878.

122 SG389-832F N-cyclohexyl-2-(2,4,5-trifluorophenyl)imidazo[1,2-a]pyridin- 3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.14 (dt, J= 1.1, 6.9, 1H), 7.57 (dt, J= 1.1, 9.1, 1H), 7.35 (tt, J =6.4, 8.4, 1H), 7.15 (ddd, J= 1.3, 6.6, 9.1, 1H), 7.03 (t, J= 8.1, 1H), 6.81 (td, J = 1.1,6.8, 1H), 3.11 (s, 1H), 2.67 (m, 1H), 1.75 (m, 2H), 1.69 - 1.56 (m, 2H), 1.56-1.38 (m, 1H), 1.07 (m, 5H). 1 ³C NMR (101 MHz, CDCI ₃) δ 161.95, 161.88, 159.48, 159.41, 142.03, 129.69, 123.82, 122.76, 117.76, 111.78, 111.65, 111.52, 56.46,34.04,25.58,24.70. HRMS (ESI): m/z 346.1534 (M+H) ⁺; calc. for Ci ₉Hi ₉N ₃F ₃: 346.1531.

123SG389-834E N-cyclopentyl-2-(2-fluorophenyl)imidazo[1,2-a]pyridin-3-amin e ¹H NMR (200 MHz, CDCI ₃) δ 8.15 (d, J = 6.9, 1 H), 7.92 (td, J = 2.2, 7.5, 1 H), 7.53 (d, J = 9.0, 1 H), 7.29 (ddd, J = 4.8, 8.8, 13.0, 2H), 7.13 (dd, J = 9.4, 16.2, 2H), 6.75 (t, J = 6.3, 1 H), 3.55 - 3.15 (m, 2H), 1.77 - 1.09 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 161.82, 156.95, 141.45, 131.43, 131.35, 129.31 , 129.14, 124.53, 124.46, 124.17, 122.70, 116.93, 1 15.65, 115.18, 11 1.70, 59.30, 33.09, 23.16. HRMS (ESI): m/z 296.1566 (M+H) ⁺; calc. for Ci ₈H ₁₉N ₃F: 296.1563.

124 SM60 N,2-dicyclohexylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.07 - 7.97 (m, 1 H), 7.53 - 7.43 (m, 1 H), 7.04 (ddd, J = 1.2, 6.5, 8.9, 1 H), 6.71 (td, J = 0.8, 6.6, 1 H), 3.02 - 2.59 (m, 2H), 2.03 - 1.51 (m, 13H),

1.51 - 1.00 (m, 8H).

¹³C NMR (50 MHz, CDCI3) δ 144.01 , 141.36, 138.21 , 122.68, 122.43, 1 16.98, 1 10.93,

57.21 , 36.47, 34.28, 33.02, 26.91 , 26.04, 25.86, 24.95.

HRMS (ESI): m/z 298.2261 (M+H) ⁺; calc. for Ci ₉H ₂₈N ₃: 298.2283.

125 SM2 N-cyclohexyl-2-(4-fluorophenyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.13 - 7.92 (m, 2H), 7.52 (dt, J = 1.0, 9.1 , 1 H), 7.22 - 6.97 (m, 2H), 6.77 (td, J = 1.1 , 6.8, 1 H), 3.31 - 2.47 (m, 2H), 1.93 - 1.40 (m, 4H), 1.40 - 0.86 (m, 4H). 1 ³C NMR (50 MHz, CDCI ₃) δ 164.7, 160.0, 142.1 , 131.3, 129.6, 129.4, 124.9, 124.0, 123.4, 117.9, 116.4, 115.7, 1 12.2, 57.3, 35.3, 26.1 , 25.0. HRMS (ESI): m/z 310.1721 (M+H) ⁺; calc. for Ci ₉H ₂iN ₃F: 310.1720.

126 SM61 N,2-dicyclohexyl-8-methylimidazo[1 ,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 7.89 (dd, J = 0.9, 7.0, 1 H), 6.83 (d, J = 6.8, 1 H), 6.61 (t, J

= 6.8, 1 H), 3.01 - 2.65 (m, 2H), 2.57 (s, 3H), 2.05 - 1.52 (m, 15H), 1.52 - 1.32 (m, 4H),

1.32 - 1.02 (m, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.45, 138.22, 126.60, 123.69, 121.57, 120.35, 110.81 ,

57.34, 37.09, 34.29, 32.90, 26.95, 25.96, 25.89, 24.99, 16.93. HRMS (ESI): m/z 312.2404 (M+H) ⁺; calc. for C ₂₀H ₃₀N ₃: 312.2440.

127 SM62 N,2-dicyclohexyl-7-methylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.89 (d, J = 7.2, 1 H), 7.23 (s, 1 H), 6.54 (dd, J = 1.3, 6.8, 1 H), 2.98 - 2.55 (m, 2H), 2.35 (s, 3H), 1.96 - 1.66 (m, 10H), 1.66 - 1.48 (m, 3H), 1.48 - 1.30 (m, 3H), 1.30 - 1.00 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 137.08, 133.51 , 128.81 , 126.28, 121.76, 1 15.49, 113.53, 57.35, 36.49, 34.25, 33.00, 26.94, 26.06, 25.89, 24.96, 21.23.

HRMS (ESI): m/z 312.2409 (M+H) ⁺; calc. for C ₂₀H ₃₀N ₃: 312.2440.

128 SM63 N,2-dicyclohexyl-6-methylimidazo[1 ,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 7.77 (s, 1 H), 7.37 (d, J = 9.1 , 1 H), 6.89 (dd, J = 1.7, 9.1 , 1 H), 2.97 - 2.78 (m, 2H), 2.31 (s, 3H), 2.06 - 1.49 (m, 13H), 1.34 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.91 , 140.49, 125.77, 123.03, 120.41 , 120.1 1 , 116.36, 57.13, 36.46, 34.26, 33.04, 26.94, 26.06, 25.88, 24.97, 18.38. HRMS (ESI): m/z 312.2408 (M+H) ⁺; calc. for C ₂₀H ₃₀N ₃: 312.2440.

129 SM64 N,2-dicyclohexyl-5-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.32 (d, J = 8.2, 1 H), 7.07 - 6.74 (m, 1 H), 6.34 (d, J = 6.8, 1 H), 2.88 (s, 3H), 2.70 (m, 2H), 2.00 - 1.53 (m, 13H), 1.52 - 0.98 (m, 8H). 1 ³C NMR (50 MHz, CDCI ₃) δ 146.00, 143.08, 135.88, 124.67, 122.94, 1 15.28, 112.64, 59.65, 36.23, 33.44, 32.87, 26.93, 25.96, 25.15, 19.76. HRMS (ESI): m/z 312.2428 (M+H) ⁺; calc. for C ₂₀H ₃₀N ₃: 312.2440.

130 SM66 2-cyclohexyl-N-cyclopentylimidazo[1 ,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 8.03 (dd, J = 0.8, 6.7, 1 H), 7.47 (dd, J = 0.9, 9.0, 1 H), 7.13 - 6.90 (m, 1 H), 6.70 (t, J = 6.7, 1 H), 3.59 (m, 1 H), 3.00 - 2.49 (m, 1 H), 2.25 - 0.94 (m, 19H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.25, 141.35, 123.99, 122.73, 122.30, 1 17.01 , 110.94,

59.92, 36.53, 33.53, 33.00, 26.91 , 26.03, 23.60.

HRMS (ESI): m/z 284.2106 (M+H) ⁺; calc. for Ci ₈H ₂₆N ₃: 284.2127.

131 SM67 2-cyclohexyl-N-cyclopentyl-8-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.91 (d, J = 6.3, 1 H), 6.84 (d, J = 6.8, 1 H), 6.62 (t, J = 6.7, 1 H), 3.59 (m, 1 H), 2.99 - 2.64 (m, 1 H), 2.57 (s, 3H), 2.16 - 0.77 (m, 19H). 1 ³C NMR (50 MHz, CDCI ₃) δ 143.58, 126.58, 124.38, 123.88, 121.70, 120.19, 110.86, 60.00, 37.06, 33.52, 32.84, 26.92, 25.94, 23.60, 16.88. HRMS (ESI): m/z 298.2234 (M+H) ⁺; calc. TOr Ci ₉H ₂₈N ₃: 298.2283.

132 SM68 2-cyclohexyl-N-cyclopentyl-7-methylimidazo[1 ,2-a]pyιϊdin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 7.92 (d, J = 6.5, 1 H), 7.26 (d, J = 6.4, 1 H), 6.57 (t, J = 6.6, 1 H), 2.88 - 2.61 (m, 1 H), 2.29 (s, 3H), 2.08 - 1.31 (m, 12H), 1.31 - 1.00 (m, 7H).

¹³C NMR (50 MHz, CDCI3) δ 144.2, 142.6, 134.4, 123.3, 122.6, 116.1 , 1 15.3, 60.8,

37.4, 35.38, 34.3, 27.2, 26.5, 25.7, 21.6.

HRMS (ESI): m/z 298.2247 (M+H) ⁺; calc. for Ci ₉H ₂₈N ₃: 298.2283.

133 SM69 2-cyclohexyl-N-cyclopentyl-6-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.81 (s, 1 H), 7.42 (d, J = 9.1 , 1 H), 6.92 (d, J = 9.3, 1 H), 3.69 - 3.48 (m, 1 H), 2.91 - 2.58 (m, 1 H), 2.32 (s, 3H), 2.00 - 0.98 (m, 19H). 1 ³C NMR (50 MHz, CDCI ₃) δ 143.87, 140.64, 139.16, 138.19, 125.96, 123.66, 120.80, 119.99, 1 16.31 , 1 14.35, 59.76, 36.47, 33.48, 32.97, 29.29, 26.92, 26.02, 25.64, 23.60, 18.33.

HRMS (ESI): m/z 298.2250 (M+H) ⁺; calc. for Ci ₉H ₂₈N ₃: 298.2283.

134 SM70 2-cyclohexyl-N-cyclopentyl-5-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.36 (t, J = 7.4, 1 H), 7.03 - 6.78 (m, 1 H), 6.35 (t, J = 7.3, 1 H), 4.01 - 3.24 (m, 4H), 2.92 (s, 2H), 2.71 - 2.50 (m, 2H), 2.50 - 2.07 (m, 4H), 2.04 -

0.96 (m, 27H).

¹³C NMR (50 MHz, CDCI ₃) δ 145.55, 136.00, 125.97, 123.29, 122.79, 122.74, 115.31 ,

115.22, 115.09, 112.86, 112.52, 1 12.28, 62.69, 36.24, 32.94, 32.89, 26.99, 26.87,

26.01 , 23.71 , 19.74. HRMS (ESI): m/z 298.2251 (M+H) ⁺; calc. for Ci ₉H ₂₈N ₃: 298.2283.

135 SM52 N-cyclohexyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.06 - 7.95 (m, 1 H), 7.58 - 7.44 (m, 1 H), 7.44 - 7.1 1 (m, 5H), 7.05 (ddd, J = 1.2, 6.7, 8.8, 1 H), 6.71 (t, J = 6.7, 1 H), 4.33 (q, J = 7.1 , 1 H), 2.87 - 2.28 (m, 2H), 1.98 - 1.43 (m, 8H), 1.43 - 0.78 (m, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 145.64, 142.00, 141.09, 128.41 , 128.35, 127.97, 127.43,

126.01 , 122.77, 122.43, 117.07, 1 11.08, 57.20, 37.99, 34.13, 25.75, 24.90, 24.80,

21.71.

HRMS (ESI): m/z 320.2073 (M+H) ⁺; calc. for C ₂₁ H ₂₆N ₃: 320.2127. 136 SM53 N-cyclohexyl-8-methyl-2-(1 -phenylethyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.98 - 7.83 (m, 1 H), 7.62 - 7.10 (m, 5H), 6.95 - 6.83 (m, 1 H), 6.64 (t, J = 6.8, 1 H), 4.42 (q, J = 7.1 , 1 H), 2.65 (s, 3H), 2.52 - 2.23 (m, 1 H), 1.84 (d, J = 7.2, 3H), 1.77 - 1.47 (m, 5H), 1.36 - 0.90 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 145.60, 141.51 , 141.35, 128.28, 127.57, 126.75, 125.95, 124.79, 121.56, 120.39, 110.91 , 57.38, 38.31 , 34.02, 25.79, 24.92, 21.71 , 16.74. HRMS (ESI): m/z 334.2242 (M+H) ⁺; calc. for C ₂₂H ₂₈N ₃: 334.2283.

137 SM54 N-cyclohexyl-7-methyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.92 (m, 1 H), 7.42-7.14 (m, 6H), 6.65 (dd, 1 H), 4.32 (q, 1 H), 2.78 (s, 1 H), 2.31 (s, 1 H), 1.83 (d, 3H), 1.88-1.54 (m, 5H), 1.29-1.04 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 146.8, 142.0, 134.7, 129.3, 128.4, 128.0, 127.5, 126.8, 123.1 , 121.8, 116.7, 115.6, 59.8, 39.5, 34.8, 26.6, 25.3, 23.9, 22.2. HRMS (ESI): m/z 334.2255 (M+H) ⁺; calc. for C ₂₂H ₂₈N ₃: 334.2283.

138 SM55 N-cyclohexyl-6-methyl-2-(1 -phenylethyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.84 - 7.67 (m, 1 H), 7.54 - 7.00 (m, 6H), 6.99 - 6.78 (m, 1 H), 4.30 (q, J = 7.1 , 1 H), 2.89 - 2.44 (m, 2H), 2.30 (s, 3H), 1.74 (d, J = 3.7, 3H), 1.72 - 1.48 (m, 6H), 1.44 - 0.83 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 159.24, 145.78, 141.86, 140.19, 128.31 , 127.41 , 125.93, 125.85, 120.57, 120.08, 116.43, 57.10, 37.98, 34.09, 25.76, 24.91 , 21.72, 18.32. HRMS (ESI): m/z 334.2257 (M+H) ⁺; calc. for C ₂₂H ₂₈N ₃: 334.2283.

139 SM56 N-cyclohexyl-5-methyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.59 - 7.02 (m, 8H), 6.92 (dd, J = 6.8, 8.9, 1 H), 6.42 - 6.29 (m, 1 H), 4.30 (q, J = 7.1 , 1 H), 3.68 (s, 1 H), 2.84 (s, 3H), 1.76 (d, J = 7.2, 3H), 1.72 - 1.46 (m, 4H), 1.46 - 0.83 (m, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 145.91 , 143.89, 142.83, 136.00, 128.24, 127.41 , 125.83, 123.1 1 , 115.40, 112.92, 59.27, 37.67, 33.57, 33.44, 25.88, 25.18, 24.95, 21.97, 19.81. HRMS (ESI): m/z 334.2255 (M+H) ⁺; calc. for C ₂₂H ₂₈N ₃: 334.2283.

140 SM51 N-cyclopentyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.08 - 7.90 (m, 1H), 7.60-7.43 (m, 1H), 7.43-7.11 (m, 5H), 7.06 (ddd, J = 1.4, 6.7, 9.0, 1H), 6.71 (td, J = 1.2, 6.8, 1H), 4.35 (q, J= 7.1, 1H), 3.61 - 3.22 (m, 1 H), 2.65 - 1.98 (m, 2H), 1.86 - 1.75 (m, 3H), 1.75 - 1.05 (m, 9H). ¹³C NMR (50 MHz, CDCI ₃) δ 145.64, 142.08, 141.11, 128.74, 128.34, 127.42, 122.79, 122.28, 117.18, 111.11, 59.75, 37.93, 33.57, 33.41, 23.55, 21.77. HRMS (ESI): m/z 306.1950 (M+H) ⁺; calc. for C ₂₀H ₂₄N ₃: 306.1970.

141 SM72 N-cyclopentyl-8-methyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyιϊdin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.91 (d, J= 7.3, 1H), 7.51 -7.10(m, 5H), 6.89 (d, J= 6.8, 1H), 6.65 (t, J= 6.7, 1H), 4.43 (q, J = 7.2, 1H), 3.44 (dt, J = 5.1, 10.2, 1H), 2.65 (s, 3H),

1.83 (d, J = 7.2, 3H), 1.79 - 1.11 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 145.54, 141.38, 128.27, 127.54, 126.79, 125.94, 125.54,

121.71, 120.22, 111.01, 59.93, 38.19, 33.46, 33.36, 23.57, 21.75, 16.74.

HRMS (ESI): m/z 320.2105 (M+H) ⁺; calc. for C ₂i H ₂₆N ₃: 320.2127.

142 SM73 N-cyclopentyl-7-methyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.89 (d, J = 6.9, 1H), 7.52 - 7.01 (m, 5H), 6.54 (dd, J = 1.6, 6.9, 1 H), 4.32 (q, J = 7.2, 1 H), 3.45 (dt, J = 5.6, 11.0, 1 H), 2.35 (s, 3H), 1.77 (d, J = 7.2, 3H), 1.73 - 1.44 (m, 5H), 1.44 - 1.04 (m, 3H). 1 ³C NMR (50 MHz, CDCI ₃) δ 145.76, 141.63, 141.59, 133.64, 128.30, 127.43, 125.92, 124.63, 121.61, 115.65, 113.71, 59.86, 37.88, 33.51, 33.38, 23.57, 21.75, 21.19. HRMS (ESI): m/z 320.2121 (M+H) ⁺; calc. for C ₂i H ₂₆N ₃: 320.2127.

143 SM74 N-cyclopentyl-6-methyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.81 - 7.73 (m, 1 H), 7.55 - 7.06 (m, 5H), 6.91 (dd, J=M, 9.1, 1H), 4.32 (q, J= 7.2, 1H), 3.58-3.31 (m, 1H), 2.30 (s, 3H), 1.77 (d, J= 7.2, 3H), 1.72- 1.09 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 145.81, 141.83, 140.20, 138.23, 128.37, 127.46, 127.31, 126.00, 120.72, 120.02, 116.59, 59.67, 37.97, 33.60, 23.62, 21.83, 18.40. HRMS (ESI): m/z 320.2095 (M+H) ⁺; calc. for C _2i H ₂₆N ₃: 320.2127.

144 SM75 N-cyclopentyl-5-methyl-2-(1-phenylethyl)imidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.46 - 7.03 (m, 6H), 6.93 (dd, J = 6.9, 8.9, 1 H), 6.36 (d, J = 6.7, 1 H), 4.34 (q, J = 7.1 , 1 H), 3.49 (dt, J = 5.7, 1 1.2, 1 H), 2.85 (s, 3H), 1.77 (d, J = 7.2, 3H), 1.73 - 1.07 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 145.96, 143.65, 142.86, 136.02, 128.27, 127.42, 127.01 , 125.86, 123.16, 115.49, 1 12.93, 62.31 , 37.53, 33.15, 32.74, 23.74, 23.61 , 22.04, 19.68. HRMS (ESI): m/z 320.2106 (M+H) ⁺; calc. for C ₂i H ₂₆N ₃: 320.2127.

145 SM3 N-cyclohexyl-2-(2,3,6-trichlorophenyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.23 - 8.07 (m, 1 H), 7.62 - 7.50 (m, 1 H), 7.47 (d, J = 8.7, 1 H), 7.36 (d, J = 8.7, 1 H), 7.18 (dd, J = 1.3, 6.7, 1 H), 6.82 (td, J = 0.9, 6.7, 1 H), 2.77 (m,

2H), 1.85 - 1.35 (m, 3H), 1.35 - 0.71 (m, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.56, 134.79, 134.48, 133.04, 131.85, 130.54, 128.27,

126.61 , 123.79, 122.90, 117.81 , 11 1.69, 56.63, 33.84, 25.63, 24.58.

HRMS (ESI): m/z 394.0645 (M+H) ⁺; calc. for Ci ₉Hi ₉N ₃CI ₃: 394.0645.

146 SM4 N-cyclohexyl-2-(2-fluoro-3-methoxyphenyl)imidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.29 - 8.03 (m, 1 H), 7.60 - 7.39 (m, 2H), 7.33 - 7.05 (m, 2H), 6.97 (td, J = 1.6, 8.2, 1 H), 6.77 (td, J = 1.1 , 6.8, 1 H), 3.93 (s, 3H), 3.72 - 3.26 (m, 1 H), 2.91 - 2.54 (m, 1 H), 1.94 - 1.36 (m, 5H), 1.33 - 0.81 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 152.17, 148.23, 147.99, 147.32, 142.22, 127.26, 124.54, 123.96, 123.56, 117.67, 1 12.66, 1 11.74, 56.95, 56.67, 34.31 , 25.93, 25.14. HRMS (ESI): m/z 340.1824 (M+H) ⁺; calc. for C ₂₀H ₂₃N ₃OF: 340.1825.

147 SM6 2-(3-chloro-2-fluorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.27 - 8.03 (m, 1 H), 7.81 (ddd, J = 1.8, 6.6, 8.4, 1 H), 7.64 - 7.47 (m, 1 H), 7.40 (ddd, J = 1.8, 7.1 , 8.0, 1 H), 7.31 - 7.03 (m, 2H), 6.80 (td, J = 1.2, 6.8, 1 H), 3.56 - 3.17 (m, 1 H), 2.87 - 2.50 (m, 1 H), 1.89 - 1.33 (m, 5H), 1.10 (d, J = 7.0, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 157.31 , 152.40, 142.05, 129.94, 129.87, 129.58, 127.10, 124.93, 124.84, 124.01 , 122.99, 1 17.47, 1 11.64, 56.74, 34.04, 25.62, 24.79. HRMS (ESI): m/z 344.1329 (M+H) ⁺; calc. for Ci ₉H ₂₀N ₃FCI: 344.1330.

148 SM7 2-(4-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.13 - 7.98 (m, 3H), 7.53 (d, J = 9.0, 1H), 7.46 - 7.37 (m, 2H), 7.14 (dd, J = 7.8, 9.1, 1H), 6.79 (t, J = 6.8, 1H), 3.13-2.84 (m, 2H), 1.95- 1.46 (m, 6H), 1.22 (m, 4H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.65, 133.09, 132.93, 128.58, 128.26, 123.99, 122.60, 117.45, 111.62, 56.87, 34.23, 25.72, 24.82.

HRMS (ESI): m/z 326.1422 (M+H) ⁺; calc. for Ci ₉H ₂i N ₃CI: 326.1424.

149 SM8 N-cyclohexyl-2-(2-(trifluoromethyl)phenyl)imidazo[1 ,2-a]pyιϊdin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.28 - 7.99 (m, 1H), 7.85 - 7.71 (m, 1H), 7.66 - 7.40 (m, 4H), 7.13 (ddd, J = 1.3, 6.7, 9.0, 1H), 6.80 (td, J = 1.1, 6.8, 1H), 3.28 - 2.83 (m, 1H),

2.66 (m, 1 H), 1.90 - 1.35 (m, 5H), 1.23 - 0.80 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.06, 138.17, 135.28, 132.83, 131.21, 128.11, 126.85,

126.14 (q, J= 5.1, 1H), 123.49, 122.77, 121.40, 117.59, 111.50, 56.25, 33.81, 25.63,

24.51. HRMS (ESI): m/z 360.1688 (M+H) ⁺; calc. for C ₂₀H ₂I N ₃F ₃: 360.1688.

150 SM11 N-cyclopentyl-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-amin e

¹H NMR (200 MHz, CDCI ₃) δ 8.21 - 7.90 (m, 3H), 7.55 (dt, J= 1.0, 9.1, 1H), 7.22 - 6.97 (m, 3H), 6.78 (td, J = 1.0, 6.8, 1 H), 3.63 (m, 1 H), 1.93 - 1.27 (m, 9H). 1 ³C NMR (50 MHz, CDCI ₃) δ 164.68, 159.78, 141.48, 138.21, 129.01, 128.85, 124.17, 122.53, 117.36, 115.57, 115.15, 111.77,59.20,33.55,23.64. HRMS(ESI): m/z 296.1560 (M+H) ⁺; calc. for Ci ₈H ₁₉N ₃F: 296.1563.

151 SM12 N-cyclopentyl^-octylimidazoπ^-aJpyridin-S-amine 1H NMR (200 MHz, CDCI ₃) δ 8.03 (d, J = 6.8, 1H), 7.45 (d, J = 9.0, 1H), 7.05 (ddd, J = 1.2, 6.5, 8.7, 1 H), 6.71 (td, J = 1.0, 6.8, 1 H), 3.71 - 3.45 (m, 1 H), 2.88 - 2.51 (m, 2H), 1.92- 1.67 (m, 7H), 1.67 - 1.42 (m, 5H), 1.42-1.11 (m, 10H), 0.87 (m, 2H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.31, 139.81, 126.46, 122.81, 122.24, 116.83, 110.95, 59.79, 33.55, 31.90, 29.86, 29.67, 29.49, 29.28, 27.51, 23.60, 22.67, 14.08. HRMS (ESI): m/z 314.2595 (M+H) ⁺; calc. for C ₂₀H ₃₂N ₃: 314.2596.

152 SM13 N-cyclopentyl-2-(2,3,6-trichlorophenyl)imidazo[1,2-a]pyridin -3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.21 - 8.10 (m, 1H), 7.59 - 7.50 (m, 1H), 7.50 - 7.41 (m, 1H), 7.41 -7.33 (m, 1H), 7.16 (ddd, J = 1.0, 6.5, 8.0, 1H), 6.82 (td, J = 0.8, 6.7, 1H), 3.56 - 3.28 (m, 2H), 2.79 (d, J = 5.6, 1 H), 1.79 - 1.40 (m, 7H), 1.40 - 1.04 (m, 4H). ¹³C NMR (50 MHz, CDCI ₃) δ 148.09, 141.46, 137.64, 134.80, 134.78, 134.50, 131.85, 130.56, 130.01, 128.88, 128.25, 127.27, 123.88, 122.73, 117.79, 114.22, 111.76, 107.50, 59.43,33.38,23.41. HRMS (ESI): m/z 380.0490 (M+H) ⁺; calc. for Ci ₈Hi ₇N ₃CI ₃: 380.0488.

153 SM14 N-cyclopentyl-2-(2-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyri din-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.14 (d, J = 6.9, 1H), 7.65 - 7.35 (m, 2H), 7.26 - 7.03 (m, 2H), 6.95 (td, J= 1.6, 8.2, 1H), 6.75 (t, J= 6.8, 1H), 3.91 (s, 3H), 3.53-3.22 (m, 2H), 1.76 - 1.07 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 151.87, 147.84, 147.60, 147.01, 141.78, 131.51, 127.51, 124.16, 124.07, 123.62, 122.67, 117.29, 112.37, 111.37, 59.40, 56.29, 33.13, 23.24. HRMS (ESI): m/z 326.1668 (M+H) ⁺; CaICfOrCi ₉H ₂IN ₃OF: 326.1669.

154 SM15 N-cyclopentyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.18 - 7.92 (m, 1H), 7.49 (m, 1H), 7.14 - 6.94 (m, 1H), 6.82 - 6.61 (m, 1 H), 3.80 - 3.47 (m, 1 H), 3.32 - 3.02 (m, 1 H), 2.90 - 2.66 (m, 1 H), 1.93 - 1.68 (m, 4H), 1.68 - 1.43 (m, 4H), 1.38 (d, J = 9.0, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 160.21, 155.76, 138.10, 126.18, 116.34, 105.78, 105.24,

58.19, 37.28, 37.04, 34.17, 25.09, 18.18, 17.96.

HRMS(ESI): m/z 244.1812 (M+H) ⁺; calc. for Ci ₅H ₂₂N ₃: 244.1814.

155 SM16 2-(3-chloro-2-fluorophenyl)-N-cyclopentylimidazo[1,2-a]pyrid in-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.23 (d, 1H), 7.92-7.86 (m, 1H), 7.55(d, 1H), 7.48-7.30 (d, 1H), 7.28-7.07 (m, 2H), 6.92-6.76 (m, 1H), 6.56-3.22 (m, 2H), 1.80-1.12 (m, 8H). 1 ³C NMR (50 MHz, CDCI ₃) δ 157.39, 152.48, 142.01, 138.19, 129.87, 129.62, 127.73, 124.93, 124.50, 124.08, 122.87, 117.52, 111.50, 59.58, 33.30, 23.31. HRMS (ESI): m/z 330.1173 (M+H) ⁺; calc. for Ci ₈Hi ₈N ₃FCI: 330.1173.

156 SM17 N-cyclopentyl-2-(pentan-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.06 (dt, J= 1.0, 6.8, 1H), 7.49 (d, J= 9.1, 1H), 7.04 (ddd,

J= 1.2,6.6,8.9, 1H), 6.71 (td, J = 0.9, 6.8, 1H), 3.64 (dt, J= 5.3, 10.8, 1H), 3.02 - 2.73 (m, 1H), 2.62 (ddd, J = 6.4, 8.2, 14.6, 1H), 1.96 - 1.68 (m, 8H), 1.68 - 1.41 (m, 4H), 1.37 (d, J = 6.8, 1 H), 0.82 (t, J = 7.4, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 142.09, 141.51, 126.28, 122.65, 122.26, 116.94, 110.72, 60.03, 40.98, 33.58, 28.25, 23.65, 12.60. HRMS(ESI): m/z 272.2125 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

157 SM18 N-cyclopentyl-2-(2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyr idin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.13 (d, J = 6.9, 1H), 7.78 (d, J = 7.5, 1H), 7.66 - 7.41 (m, 4H), 7.23 - 7.03 (m, 1 H), 6.81 (td, J = 0.9, 6.7, 1 H), 3.52 - 3.21 (m, 1 H), 3.06 - 2.78 (m, 1H), 1.40 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.03, 135.34, 132.87, 131.23, 129.95, 128.14, 126.72, 126.17 (q, J= 5.1), 123.60, 122.64, 121.42, 117.65, 111.59,59.16,33.33,23.35. HRMS(ESI): m/z 346.1531 (M+H) ⁺; calc. for Ci ₉H ₁₉N ₃F ₃: 346.1531.

158 SM19 N-cyclopentyl-2-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin -3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.15-8.06 (m, 1H), 7.52 (dt, J= 1.0, 9.0, 1H), 7.26 (d, J = 5.1, 1H), 7.11 (ddd, J= 1.3, 6.7, 9.0, 1H), 6.94 (d, J= 5.1, 1H), 6.77 (td, J= 1.1, 6.8, 1 H), 3.82 - 3.25 (m, 1 H), 3.22 - 2.92 (m, 1 H), 2.43 (s, 4H), 1.88 - 1.56 (m, 5H), 1.55 - 1.31 (m, 4H). 1 ³C NMR (50 MHz, CDCI ₃) δ 141.36, 135.77, 130.47, 129.73, 126.57, 124.33, 124.21, 123.50, 122.49, 117.47, 111.46, 59.35, 33.32, 23.50. HRMS(ESI): m/z 298.1383 (M+H) ⁺; calc. for Ci ₇H ₂₀N ₃S: 298.1378.

159 SM20 N-cyclopentyl-2-cyclopropylimidazo[1,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 8.01 (d, J =6.7, 1H), 7.40 (d, J = 8.9, 1H), 7.21 -6.91 (m,

1 H), 6.91 - 6.47 (m, 1 H), 3.85 - 3.53 (m, 1 H), 3.14 - 2.48 (m, 1 H), 2.21 - 1.69 (m, 4H),

1.69 - 1.40 (m, 4H), 1.23 - 0.79 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.47, 140.87, 138.47, 123.06, 122.12, 116.94, 111.17,

60.15,33.82,23.86,8.45,8.00. HRMS(ESI): m/z 242.1659 (M+H) ⁺; calc. for Ci ₅H ₂₀N ₃: 242.1657.

160 SM21 2-sec-butyl-N-cyclopentylimidazo[1,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.13 - 7.98 (m, 1 H), 7.57 - 7.42 (m, 1 H), 7.14 - 6.98 (m, 1 H), 6.85 - 6.59 (m, 1 H), 4.55 - 3.84 (m, 1 H), 3.61 (m, 1 H), 2.86 (m, 1 H), 2.1 1 - 1.40 (m, 1 1 H), 1.34 (d, J = 6.9, 3H), 0.85 (t, J = 7.4, 2H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.56, 141.42, 124.80, 122.89, 122.29, 1 16.86, 110.94, 59.92, 33.54, 33.51 , 29.84, 23.58, 20.73, 12.61.

HRMS (ESI): m/z 258.1970 (M+H) ⁺; calc. for Ci ₆H ₂₄N ₃: 258.1970.

161 SM24 2-sec-butyl-N-cyclohexylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.14 - 7.93 (m, 1 H), 7.48 (m, 1 H), 7.04 (ddd, J = 1.2, 6.7, 8.8, 1 H), 6.71 (td, J = 1.1 , 6.9, 1 H), 3.10 - 2.63 (m, 2H), 2.12 - 1.48 (m, 8H), 1.48 -

1.06 (m, 8H), 0.85 (t, J = 7.3, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.77, 141.75, 124.39, 123.01 , 122.71 , 1 17.13, 111.12,

57.58, 34.55, 33.63, 30.16, 26.09, 25.23, 21.07, 12.87.

HRMS (ESI): m/z 272.2127 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

162 SM26 6-bromo-2-(2-chlorophenyl)-N-cyclohexyl-7-methylimidazo[1 ,2-a]pyridin-3- amine

¹H NMR (200 MHz, CDCI ₃) δ 8.30 (s, 1 H), 7.71 - 7.54 (m, 1 H), 7.52 - 7.12 (m, 4H), 3.22 (d, J = 5.6, 1 H), 2.78 - 2.51 (m, 1 H), 2.45 (s, 3H), 1.87 - 1.33 (m, 5H), 1.23 - 0.78 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 140.87, 135.76, 134.14, 133.78, 132.60, 132.42, 129.45, 129.16, 126.86, 125.74, 122.98, 1 16.60, 1 10.69, 56.52, 33.79, 25.64, 24.56, 22.53. HRMS (ESI): m/z 418.0686 (M+H) ⁺; calc. for C ₂₀H ₂₂N ₃CIBr: 418.0686.

163 SM27 2-(2-chlorophenyl)-N-cyclohexyl-6-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.91 (s, 1 H), 7.74 - 7.54 (m, 1 H), 7.52 - 7.40 (m, 2H), 7.40 - 7.18 (m, 2H), 6.98 (dd, J = 1.7, 9.2, 1 H), 3.40 - 3.07 (m, 1 H), 2.82 - 2.51 (m, 1 H), 2.35 (s, 3H), 1.91 - 1.31 (m, 5H), 1.23 - 0.80 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 140.71 , 135.00, 134.20, 132.48, 129.31 , 128.86, 126.74, 125.92, 121.02, 120.30, 116.84, 56.26, 33.80, 25.64, 24.55, 18.37. HRMS (ESI): m/z 340.1582 (M+H) ⁺; calc. for C ₂₀H ₂₃N ₃CI: 340.1581.

164 SM28 2-(2-chlorophenyl)-N-cyclohexyl-7-methylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 8.11 (d, 1 H), 7.72-7.68 (m, 1 H), 7.53-7.26 (m, 4H), 6.72 (dd, 1 H), 3.24 (s, 1 H), 2.78 (s, 1 H), 2.45 (s, 3H), 1.80-1.42 (m, 5H), 1.23-0.97 (m, 5H). ¹³C NMR (50 MHz, CDCI ₃) δ 142.4, 135.2, 134.4, 134.7, 133.9, 130.2, 129.3, 127.7, 126.2 123.3, 116.6, 115.3, 57.4, 34.7, 26.4, 25.2, 21.8. HRMS (ESI): m/z 340.1581 (M+H) ⁺; calc. for C ₂₀H ₂₃N ₃CI: 340.1581.

165 SM29 2-(2-chlorophenyl)-N-cyclohexyl-8-methylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.92 (s, 1 H), 7.73-7.67 (m, 1 H), 7.58-7.22 (m, 4H), 7.03- 6.92 (dd, 1 H), 3.37 (s, 1 H), 2.72 (s, 1 H), 2.38 (s, 3H),1.85-1.42 (m, 5H), 1.22-1.08 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 146.1 , 142.8, 141.3, 139.5, 135.9, 133.3, 130.2, 129.6,

127.2, 122.7, 121.3, 118.6, 57.0, 34.2, 26.5, 25.9, 19.5.

HRMS (ESI): m/z 340.1581 (M+H) ⁺; calc. for C ₂₀H ₂₃N ₃CI: 340.1581.

166 SM30 2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.71-7.68 (m, 1 H), 7.52-7.26 (m, 4H), 7.12-7.08 (m, 1 H), 6.53-6.46 (d, 1 H), 3.25-3.18 (m, 1 H), 3.03 (s, 3H), 2.65 (s, 1 H), 1.80-1.45 (m, 5H), 1.26- 0.81 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 143.15, 137.29, 136.64, 134.56, 132.65, 132.48, 129.22, 128.87, 128.05, 126.71 , 123.78, 1 15.74, 1 13.16, 58.72, 33.39, 25.67, 24.95, 19.84. HRMS (ESI): m/z 340.1581 (M+H) ⁺; calc. for C ₂₀H ₂₃N ₃CI: 340.1581.

167 SM32 6-bromo-2-(2-chlorophenyl)-N-cyclopentyl-7-methylimidazo[1 ,2-a]pyridin-3- amine 1H NMR (200 MHz, CDCI ₃) δ 8.31 (s, 1 H), 7.65 (dd, J = 2.5, 6.9, 1 H), 7.53 - 7.11 (m, 4H), 3.50 - 3.25 (m, 1 H), 3.24 - 3.07 (m, 1 H), 2.44 (s, 3H), 1.77 - 1.04 (m, 8H). 1 ³C NMR (50 MHz, CDCI ₃) δ 140.72, 135.51 , 134.08, 133.66, 132.60, 132.36, 129.39, 129.15, 126.81 , 126.38, 122.80, 1 16.51 , 1 10.69, 59.33, 33.13, 23.20, 22.47. HRMS (ESI): m/z 404.0528 (M+H) ⁺; calc. for Ci ₉H ₂₀N ₃CIBr: 404.0529.

168 SM33 2-(2-chlorophenyl)-N-cyclopentyl-6-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.98 - 7.90 (m, 1 H), 7.67 (dd, J = 2.2, 7.2, 1 H), 7.52 - 7.38 (m, 2H), 7.38 - 7.28 (m, 2H), 7.00 (dd, J = 1.8, 9.2, 1 H), 3.49 - 2.94 (m, 2H), 2.36 (s, 3H), 1.73 - 0.94 (m, 8H). ¹³C NMR (50 MHz, CDCI ₃) δ 142.02, 135.00, 134.23, 132.63, 132.55, 129.39, 128.97, 126.87, 126.82, 121.16, 120.27, 1 16.94, 108.37, 59.32, 33.22, 23.28, 18.24 HRMS (ESI): m/z 326.1422 (M+H) ⁺; calc. for Ci ₉H ₂i N ₃CI: 326.1424.

169 SM34 2-(2-chlorophenyl)-N-cyclopentyl-7-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.05 (d, J = 6.9, 1 H), 7.75 - 7.60 (m, 1 H), 7.46 (dd, J = 2.1 , 7.2, 1 H), 7.41 - 7.16 (m, 3H), 6.64 (dd, J = 1.5, 7.0, 1 H), 3.49 - 3.01 (m, 2H), 2.40 (s, 3H), 1.72 - 1.10 (m, 8H).

¹³C NMR (50 MHz, CDCI ₃) δ 142.19, 138.27, 134.80, 134.49, 132.88, 132.79, 129.65, 129.28, 129.20, 127.06, 122.22, 1 16.13, 114.50, 59.76, 33.45, 23.54, 21.56. HRMS (ESI): m/z 326.1422 (M+H) ⁺; calc. for Ci ₉H ₂i N ₃CI: 326.1424.

170 SM35 2-(2-chlorophenyl)-N-cyclopentyl-8-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.03 (ddd, J = 0.5, 1.0, 2.4, 1 H), 7.74 - 7.64 (m, 1 H), 7.50 - 7.42 (m, 1 H), 7.41 - 7.26 (m, 2H), 6.94 (d, J = 6.7, 1 H), 6.72 (t, J = 6.7, 1 H), 3.47 -

3.25 (m, 1 H), 3.26 - 3.00 (m, 1 H), 2.62 (s, 3H), 1.71 - 1.41 (m, 6H), 1.41 - 1.01 (m,

3H).

¹³C NMR (50 MHz, CDCI ₃) δ 141.93, 138.20, 134.64, 134.32, 132.84, 132.75, 129.35,

129.00, 127.31 , 126.90, 122.49, 120.58, 111.62, 59.43, 33.26, 23.29, 16.71. HRMS (ESI): m/z 326.1424 (M+H) ⁺; calc. for Ci ₉H ₂i N ₃CI: 326.1424.

171 SM36 2-(2-chlorophenyl)-N-cyclopentyl-5-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.76 - 7.61 (m, 1 H), 7.56 - 7.21 (m, 4H), 7.01 (dd, J = 6.9, 8.9, 1 H), 6.49 (d, J = 8.6, 1 H), 3.37 - 3.00 (m, 2H), 2.97 (s, 3H), 1.71 - 1.28 (m, 6H), 1.28 - 0.93 (m, 2H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.47, 138.45, 137.04, 134.89, 133.05, 132.97, 132.86, 129.60, 129.29, 127.11 , 124.22, 1 16.12, 1 13.55, 62.36, 32.95, 23.56, 20.16. HRMS (ESI): m/z 326.1426 (M+H) ⁺; calc. for Ci ₉H ₂i N ₃CI: 326.1424.

172 SM38 β-bromo-N-cyclopentyl^-isopropyl^-methylimidazofi ^-alpyridin-S-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.18 (s, 1 H), 7.33 (s, 1 H), 3.69 - 3.44 (m, 1 H), 3.27 - 2.96 (m, 1 H), 2.88 - 2.53 (m, 1 H), 2.41 (s, 3H), 1.97 - 1.38 (m, 8H), 1.34 (d, J = 6.8, 6H). ¹³C NMR (50 MHz, CDCI ₃) δ 145.57, 133.02, 123.33, 122.61 , 1 16.30, 109.91 , 109.74, 59.91 , 33.56, 26.32, 23.61 , 22.73, 22.44. HRMS (ESI): m/z 336.1077 (M+H) ⁺; CaICfOrCi ₆H ₂₃N ₃Br: 336.1075.

173 SM39 N-cyclopentyl-2-isopropyl-6-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.86 - 7.74 (m, 1H), 7.39 (d, J = 9.1, 1H), 6.90 (dd, J = 1.8, 9.1, 1H), 3.71 - 3.41 (m, 1H), 3.29 - 3.00 (m, 1H), 2.31 (s, 3H), 1.91 - 1.41 (m, 8H), 1.36 (d, J =6.9, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.70, 140.54, 125.88, 123.17, 120.44, 120.04, 116.42, 59.75, 33.55, 26.23, 23.64, 22.85, 18.37.

HRMS(ESI): m/z 258.1972 (M+H) ⁺; calc. for Ci ₆H ₂₄N ₃: 258.1970.

174 SM40 N-cyclopentyl-2-isopropyl-7-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.91 (d, J = 7.1, 1H), 7.24 (s, 1H), 6.54 (dd, J = 1.4, 7.1, 1 H), 3.68 - 3.46 (m, 1 H), 3.24 - 2.99 (m, 1 H), 2.35 (s, 3H), 1.90 - 1.40 (m, 8H), 1.36 (d, J= 6.9, 6H). 1 ³C NMR (50 MHz, CDCI ₃) δ 144.35, 141.78, 133.46, 121.96, 121.53, 115.42, 113.42, 59.85, 33.41, 26.15, 23.52, 22.71, 21.09. HRMS(ESI): m/z 258.1969 (M+H) ⁺; calc. for Ci ₆H ₂₄N ₃: 258.1970.

175 SM41 N-cyclopentyl-2-isopropyl-8-methylimidazo[1 ,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 8.00 - 7.82 (m, 1H), 6.97-6.75 (m, 1H), 6.62 (t, J= 6.8,

1 H), 3.72 - 3.43 (m, 1 H), 3.33 - 2.99 (m, 1 H), 2.58 (s, 3H), 1.93 - 1.67 (m, 4H), 1.67 -

1.43 (m, 4H), 1.39 (d, J= 6.9, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.27, 141.65, 126.67, 124.17, 121.68, 120.23, 110.86,

59.99, 33.59, 26.71, 23.65, 22.82, 16.87. HRMS (ESI): m/z 258.1969 (M+H) ⁺; calc. for Ci ₆H ₂₄N ₃: 258.1970.

176 SM42 N-cyclopentyl-2-isopropyl-5-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.35 (d, J = 8.9, 1H), 6.91 (dd, J = 6.8, 9.0, 1H), 6.39 - 6.30 (m, 1H), 3.63-3.38 (m, 1H), 3.15 (q, J= 6.8, 1H), 2.96-2.76 (m, 3H), 1.93-1.67 (m, 4H), 1.67 - 1.41 (m, 4H), 1.41 - 1.26 (m, 6H).

¹³C NMR (50 MHz, CDCI ₃) δ 146.39, 143.09, 135.91, 123.02, 115.29, 115.29, 112.63,

62.55, 32.91, 25.88, 23.65, 22.75, 19.68.

HRMS(ESI): m/z 258.1971 (M+H) ⁺; calc. for Ci ₆H ₂₄N ₃: 258.1970. 177 SM44 6-bromo-N-cyclohexyl-2-isopropyl-7-methylimidazo[1 ,2-a]pyιϊdin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.17 (s, 1 H), 7.33 (s, 1 H), 3.08 (q, J = 6.7, 1 H), 2.96 - 2.59 (m, 2H), 2.41 (s, 3H), 2.02 - 1.46 (m, 6H), 1.34 (d, J = 6.9, 6H), 1.29 - 1.07 (m, 4H). 1 ³C NMR (50 MHz, CDCI ₃) δ 145.76, 138.45, 133.21 , 122.96, 1 16.48, 1 10.14, 100.21 , 57.62, 34.47, 26.54, 26.07, 25.16, 22.97, 22.68. HRMS (ESI): m/z 350.1236 (M+H) ⁺; CaIC fOr Ci ₇H ₂₅N ₃Br: 350.1232.

178 SM45 N-cyclohexyl-2-isopropyl-6-methylimidazo[1 ,2-a]pyridin-3-amine 1H NMR (200 MHz, CDCI ₃) δ 7.78 (s, 1 H), 7.38 (d, J = 9.2, 1 H), 6.89 (dd, J = 1.7, 9.1 , 1 H), 3.23 - 3.00 (m, 1 H), 2.97 - 2.74 (m, 1 H), 2.31 (s, 3H), 1.98 - 1.47 (m, 5H), 1.35 (d, J = 6.9, 6H), 1.22 - 1.09 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.63, 140.56, 138.22, 125.82, 120.41 , 120.14, 116.41 , 57.17, 34.30, 26.22, 25.89, 24.98, 22.86, 18.39. HRMS (ESI): m/z 272.2126 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

179 SM46 N-cyclohexyl-2-isopropyl-7-methylimidazo[1 ,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 8.00 - 7.79 (m, 1 H), 7.26 (s, 1 H), 6.55 (dd, J = 1.5, 7.0, 1 H), 3.23 - 2.93 (m, 2H), 2.93 - 2.73 (m, 1 H), 2.35 (s, 3H), 1.99 - 1.44 (m, 5H), 1.35 (d, J = 6.9, 6H), 1.30 - 0.99 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.44, 142.08, 139.90, 133.86, 122.00, 1 15.73, 113.81 ,

57.62, 34.51 , 26.47, 26.14, 25.20, 23.03, 21.47.

HRMS (ESI): m/z 272.2126 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

180 SM47 N-cyclohexyl^-isopropyl-δ-methylimidazoti ^-aJpyridin-S-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.89 (d, J = 6.8, 1 H), 7.02 - 6.73 (m, 1 H), 6.61 (t, J = 6.7, 1 H), 3.28 - 3.04 (m, 1 H), 2.98 - 2.66 (m, 2H), 2.57 (s, 3H), 1.97 - 1.50 (m, 5H), 1.38 (d, J = 6.9, 6H), 1.31 - 1.04 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 153.93, 144.41 , 141.95, 126.89, 121.84, 120.62, 111.05, 57.61 , 34.57, 26.94, 26.14, 25.24, 23.08, 17.13.

HRMS (ESI): m/z 272.2123 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

181 SM48 N-cyclohexyl-2-isopropyl-5-methylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.36 (d, J = 8.8, 1H), 6.92 (dd, J = 6.7, 8.9, 1H), 6.42 - 6.29 (m, 1H), 3.24 - 3.00 (m, 1H), 2.89 (s, 3H), 1.97 - 1.51 (m, 5H), 1.35 (d, J = 6.9, 6H), 1.31 - 0.97 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.26, 141.87; 139.92, 138.47, 123.30, 115.64, 112.96, 59.90, 33.82, 26.27, 26.23, 25.46, 23.01 , 20.09.

HRMS(ESI): m/z 272.2128 (M+H) ⁺; calc. for Ci ₇H ₂₆N ₃: 272.2127.

182 SM81 N,2-bis(2-chlorophenyl)-5-methylimidazo[1,2-a]pyridin-3-amin e

¹H NMR (200 MHz, CDCI ₃) δ 7.68 - 7.49 (m, 2H), 7.49 - 7.34 (m, 1H), 7.34 - 7.20 (m, 2H), 7.14 (dd, J = 6.8, 9.1, 1H), 7.03 - 6.84 (m, 1H), 6.65 (td, J = 1.2, 7.6, 1H), 6.52 (d,

J = 6.7, 1H), 6.19(s, 1H), 6.09 (dd, J= 1.1,8.3, 1H), 2.67 (s, 3H).

¹³C NMR (50 MHz, CDCI ₃) δ 144.65, 143.60, 140.64, 138.21, 136.14, 133.24, 132.70,

131.97, 129.61, 129.48, 129.38, 127.82, 126.70, 125.31, 119.47, 118.64, 116.22,

113.90, 113.60, 18.59. HRMS (ESI): m/z 368.0733 (M+H) ⁺; calc. for C ₂₀Hi ₆N ₃CI ₂: 368.0721.

183 SM832-(2-chlorophenyl)-N-cyclohexyl-5,7-dimethylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.71 - 7.53 (m, 1H), 7.52 - 7.39 (m, 1H), 7.39 - 7.20 (m, 2H), 7.14 (s, 1H), 6.29 (s, 1H), 2.91 (s, 3H), 2.54 (m, 1H), 2.31 (s, 3H), 1.58 (m, 5H), 1.11 -0.68 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 143.77, 138.20, 135.88, 134.77, 134.58, 132.74, 132.57,

129.31, 128.86, 127.69, 126.79, 116.02, 114.18, 58.77, 33.16, 25.80, 24.76, 20.87,

19.72.

HRMS (ESI): m/z 354.1715 (M+H) ⁺; calc. for C ₂i H ₂₅N ₃CI: 354.1737.

184 SM922-(2-chlorophenyl)-N-cyclohexyl-5-phenoxyimidazo[1,2-a]p yridin-3-amine

¹H NMR (200 MHz, CDCI ₃) δ 7.68 - 7.61 (m, 1H), 7.56 - 7.41 (m, 3H), 7.39 - 7.28 (m, 3H), 7.28 -7.19 (m, 3H), 7.08 -6.89 (m, 1H), 5.91 (d, J =7.2, 1H), 2.89 - 2.80 (m, 1H), 1.78 - 1.41 (m, 6H), 1.11 - 0.81 (m, 5H). 1 ³C NMR (50 MHz, CDCI ₃) δ 156.34, 149.94, 143.46, 138.28, 134.05, 133.85, 131.01, 129.96, 129.24, 128.01, 127.34, 124.91, 120.04, 113.84, 97.02, 57.96, 33.95, 25.74, 25.07. HRMS (ESI): m/z418.1635 (M+H) ⁺; CaICfOrC ₂₅H ₂₅N ₃OCI: 418.1686. 185 SM932-(2-chlorophenyl)-N-cyclohexyl-5-ethoxyimidazo[1 ,2-a]pyιϊdin-3-amine ¹H NMR (200 MHz, CDCI ₃) δ 7.57 (dd, J = 3.3, 6.0, 1H), 7.51 - 7.39 (m, 1H), 7.38 - 7.19 (m, 2H), 7.13 (d, J= 8.9, 1H), 7.04 - 6.88 (m, 1H), 5.89 (d, J = 7.3, 1H), 4.26 (q, J = 7.0, 2H), 4.11 (s, 1H), 2.74 (s, 1H), 1.83 - 1.63 (m, 2H), 1.63 - 1.31 (m, 6H), 1.21 - 0.75 (m, 5H).

¹³C NMR (50 MHz, CDCI ₃) δ 150.94, 142.66, 134.48, 134.05, 132.58, 129.41, 128.73, 128.48, 126.29, 123.89, 110.70, 88.54, 65.45, 57.15, 33.42, 25.88, 24.57, 14.46. HRMS (ESI): m/z 370.1658 (M+H) ⁺; calc. for C ₂i H ₂₅N ₃OCI: 370.1686.

186 DG402-497204-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl) benzonitrile

¹H NMR (400 MHz, CDCI ₃) δ 8.24 (dd, J = 1.7, 8.5, 2H), 8.05 (dt, J = 1.0, 6.9, 1H), 7.69 (dd, J= 1.7, 8.5, 2H), 7.53 (dt, J= 1.0, 9.1, 1H), 7.17 (ddd, J= 1.2, 6.7, 9.1, 1H), 6.81 (td, J= 1.0, 6.8, 1H), 3.06 (d, J= 4.9, 1H), 2.95 (ddd, J = 4.6, 10.0, 14.4, 1H), 1.87- 1.76 (m, 2H), 1.76 - 1.64 (m, 2H), 1.64 - 1.51 (m, 1 H), 1.33 - 1.03 (m, 5H). 1 ³C NMR (101 MHz, CDCI ₃) δ 141.94, 139.17, 134.70, 132.16, 127.17, 126.06, 124.61, 122.63, 119.18, 117.75, 112.04, 110.20, 56.96, 34.22, 25.59, 24.77. HRMS(ESI): m/z 317.1765 (M+H) ⁺; calc. for C ₂₀H ₂I N ₄: 317.1766.

187 DG402-497223-(3-(cyclohexylamino)imidazo[1 ,2-a]pyridin-2-yl)benzonitrile 1H NMR (400 MHz, CDCI ₃) δ 8.48 (t, J= 1.6, 1H), 8.37 (dt, J= 1.5, 7.6, 1H), 8.14-7.94 (m, 1H), 7.62- 7.45 (m, 3H), 7.16 (ddd, J= 1.1, 6.7, 9.0, 1H), 6.81 (td, J= 1.0, 6.8, 1H), 3.04 (d, J = 4.7, 1H), 2.94 (ddd, J = 4.4, 10.0, 14.3, 1H), 1.88 - 1.75 (m, 2H), 1.75 -

1.63 (m, 2H), 1.63 - 1.49 (m, 1 H), 1.42 - 0.92 (m, 5H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.85, 135.91, 134.59, 130.95, 130.44, 130.33, 129.11, 125.29, 124.46, 122.58, 118.98, 117.64, 112.48, 111.96, 56.91, 34.21, 25.58, 24.76. HRMS(ESI): m/z 317.1775 (M+H) ⁺; calc. for C ₂₀H ₂I N ₄: 317.1766.

188 DG402-49744 7-chloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyridin-3- amine 1H NMR (400 MHz, CDCI ₃) δ 8.07 (d, J = 7.3, 1H), 7.64 (d, J = 5.5, 1H), 7.52 (s, 1H), 7.47 (d, J = 6.3, 1H), 7.35 (dd, J = 7.1, 12.4, 2H), 6.79 (d, J = 7.2, 1H), 3.26 (s, 1H),

2.64 (s, 1 H), 1.75 - 1.61 (m, 2H), 1.56 (s, 2H), 1.47 (s, 1 H), 1.15 - 0.91 (m, 5H).

¹³C NMR (101 MHz, CDCI ₃) δ 141.08, 135.68, 133.40, 132.41, 132.35, 130.20, 129.44, 129.28, 126.93, 126.56, 123.19, 116.16, 113.23, 56.41, 33.71, 25.49, 24.46. 189 CW23828a 2-(2-chlorophenyl)-N-cyclohexyl-6-(4-methoxyphenyl)imidazo[1 ,2- a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 8.25 (s, 1 H), 7.70 (dd, J = 1.9, 7.5, 1 H), 7.60 (dd, J = 0.7, 9.3, 1 H), 7.54 (d, J = 8.8, 2H), 7.48 (dd, J = 1.5, 7.7, 1 H), 7.43 - 7.29 (m, 3H), 7.03 (d, J = 8.8, 2H), 3.86 (s, 3H), 3.31 (d, J = 6.8, 1 H), 2.80 - 2.59 (m, 1 H), 1.78 - 1.63 (m, 2H), 1.63 - 1.51 (m, 2H), 1.51 - 1.40 (m, 1 H), 1.17 - 0.89 (m, 5H).

¹³C NMR (101 MHz, CDCI ₃) δ 159.32, 140.83, 135.58, 133.97, 132.48, 130.28, 129.41 , 129.07, 127.99, 126.88, 126.56, 125.70, 124.48, 119.32, 117.26, 1 14.43, 56.42, 55.32, 33.79, 25.55, 24.53.

190 CW23828b 2-(2-chlorophenyl)-N-cyclohexyl-5-(4-methoxyphenyl)imidazo[1 ,2- a]pyridin-3-amine

¹H NMR (400 MHz, CDCI ₃) δ 7.62 (dd, J = 2.1 , 7.3, 1 H), 7.60 - 7.53 (m, 1 H), 7.46 (d + m, J = 8.7, 3H), 7.37 - 7.26 (m, 2H), 7.14 (dd, J = 6.8, 8.9, 1 H), 6.98 (d, J = 8.6, 2H),

6.61 (dd, J = 1.0, 6.8, 1 H), 3.88 (s, 3H), 2.64 (s, 1 H), 2.00 (m, 1 H), 0.82 (m, 8H), 0.37

(m, 2H).

¹³C NMR (101 MHz, CDCI ₃) δ 159.88, 142.70, 138.01 , 135.45, 134.19, 133.32, 132.69,

130.78, 129.40, 128.92, 127.99, 127.08, 126.62, 122.99, 1 16.73, 115.26, 1 12.64, 56.36, 55.50, 32.47, 25.59, 24.34.

191 CW23825 2-(2-chlorophenyl)-N-cyclohexyl-5-o-tolylimidazo[1 ,2-a]pyridin-3-amine

192 CW23828c 2-(2-chlorophenyl)-N-cyclohexyl-6-o-tolylimidazo[1 ,2-a]pyridin-3-amine ¹H NMR (400 MHz, CDCI ₃) δ 7.65 - 7.60 (m, 1 H), 7.58 (dd, J = 1.2, 9.0, 1 H), 7.46 -

7.19 (m, 7H), 7.15 (dd, J = 6.8, 9.0, 1 H), 6.57 (dd, J = 1.2, 6.8, 1 H), 2.45 (d, J = 7.8, 1 H), 2.07 (s, 3H), 2.01 (ddd, J = 3.6, 8.5, 10.1 , 1 H), 1.41 - 0.98 (m, 5H), 0.89 - 0.65 (m, 2H), 0.58 (d, J = 12.4, 1 H), 0.41 - 0.27 (m, 1 H), 0.27 - 0.11 (m, 1 H). 1 ³C NMR (101 MHz, CDCI ₃) δ 142.26, 138.77, 137.87, 134.92, 134.19, 133.22, 132.68, 129.34, 129.24, 129.00, 128.97, 128.94, 128.53, 127.75, 127.34, 126.66, 125.06, 122.97, 116.94, 114.82, 56.76, 32.63, 32.50, 25.55, 19.77.

193 DG402-49750 2-(2-chlorophenyl)-N-cyclohexylimidazo[1 ,2-a]pyrimidin-3-amine ¹H NMR (400 MHz, CDCI ₃) δ 8.53 (dd, J = 2.1, 4.1, 1H), 8.46 (dd, J = 2.1, 6.8, 1H), 7.81 -7.70(m, 1H), 7.55- 7.43 (m, 1H), 7.38 (dqd, J= 1.8, 7.4, 14.8, 2H), 6.90 (dd, J = 4.1, 6.8, 1 H» 3.34 (d, J = 6.9, 1 H), 2.64 (dd, J = 3.4, 6.7, 1 H), 1.73 - 1.61 (m, 2H), 1.61 - 1.52 (m, 2H), 1.47 (s, 1H), 1.19-0.91 (m, 5H). 1 ³C NMR (101 MHz, CDCI ₃) δ 149.13, 144.56, 136.60, 133.27, 132.79, 132.24, 130.42, 129.45, 129.42, 127.01, 124.75, 108.09, 56.60, 33.72, 25.47, 24.46. HRMS (ESI): m/z 327.1380 (M+H) ⁺; calc. for Ci ₈H ₂₀N ₄CI: 327.1376.

194 DG 402-49752 2-(2-chlorophenyl)-N-cyclohexylimidazo[2,1-a]isoquinolin-3-a mine ¹H NMR (400 MHz, CDCI ₃) δ 8.66 (d, J = 8.0, 1H), 8.00 (d, J = 7.3, 1H), 7.75 (dd, J =

1.6, 7.5, 1 H), 7.71 (d, J = 7.0, 1 H), 7.62 - 7.57 (m, 1 H), 7.57 - 7.51 (m, 1 H), 7.48 (dd, J

= 1.2, 7.9, 1H), 7.39 (td, J = 1.4, 7.5, 1H), 7.36 - 7.30 (m, 1H), 7.07 (d, J = 7.2, 1H),

3.29 (d, J= 7.1, 1H), 2.78 -2.62 (m, 1H), 1.77 - 1.66 (m, 2H), 1.63-1.51 (m, 2H), 1.51

-1.44(m, 1H), 1.16 - 0.98 (m, 5H). 1 ³C NMR (101 MHz, CDCI ₃) δ 139.07, 134.03, 132.69, 132.61, 129.61, 129.43, 129.38,

128.97, 128.12, 127.88, 127.78, 127.05, 126.89, 123.95, 122.72, 120.44, 112.30, 56.93,

33.80, 25.62, 24.60.

HRMS (ESI): m/z 376.1587 (M+H) ⁺; calc. for C ₂₃H ₂₃N ₃CI: 376.1581.

Biological Activity

Table 1 gives selected results for the compounds of the invention against HIV-1 reverse transcriptase in an enzymatic assay and/or whole cell anti-HIV assay.

Table 1. IC50 values obtained for compounds against HIV-1 reverse transcriptase enzymatic assay and whole cell anti-HIV assay.

ND: not done Enzymatic method for determining activity against reverse transcriptase

The assay is based on a sandwich-ELISA protocol employing the ROCHE colorimetric reverse transcriptase kit (cat# 11468120910). Biotin and DIG-labelled nucleotides are incorporated into cDNA strands polymerized on an RNA template by the action of HIV-1 reverse transcriptase. The cDNA products are bound to streptavidin-coated wells of 96- well plate inserts, and their associated DIG-moieties detected by incubation with anti-

DIG antibodies conjugated to horseradish peroxidase (HRP). The amount of bound antibody is quantitated by incubation with a colorimetric HRP substrate, followed by absorbance reading at 405nm using a multiwell spectrophotometer.

To assess the inhibitory activity of test compounds, a single concentration screen (usually 50 μM) or IC50 determination may be carried out. In the single concentration screen, compounds are incubated with HIV-1 reverse trancriptase and substrate and the residual enzyme activity expressed as a percentage relative to a control without inhibitor. For IC50 determinations, 4-fold serial dilutions of the compounds are incubated with HIV-1 reverse trancriptase and substrate and the enzyme activity, expressed as a percentage relative to a control without inhibitor, plotted against inhibitor concentration to derive the concentration at which 50% enzyme inhibition (IC50) is obtained.

Cellular methods for determining anti-HIV activity

PBMC Fresh human PBMCs, seronegative for HIV and HBV, were isolated from screened donors (Interstate Blood Bank, Inc. Memphis, TN). Cells were pelleted/washed 2-3 times by low speed centrifugation and re-suspension in PBS to remove contaminating platelets. The Leukophoresed blood was then diluted 1 :1 with Dulbecco's Phosphate Buffered Saline (DPBS) and layered over 14 ml. of Lymphocyte Separation Medium (LSM; Cellgro ^® by Mediatech, Inc.; density 1.078+/-0.002 g/ml; Cat.# 85-072-CL) in a 50 mL centrifuge tube and then centrifuged for 30 minutes at 600 X g. Banded PBMCs were gently aspirated from the resulting interface and subsequently washed 2X with PBS by low speed centrifugation. After the final wash, cells were enumerated by trypan blue exclusion and re-suspended at 1 x 10 ⁷ cells/ml in RPMI 1640 supplemented with 15 % Fetal Bovine Serum (FBS), and 2 mM L-glutamine, 4 μg/ml Phytohemagglutinin (PHA-P, Sigma). The cells were allowed to incubate for 48-72 hours at 37°C. After incubation, PBMCs were centrifuged and resuspended in RPMI 1640 with 15% FBS, 2 mM L-glutamine, 100 U/ml penicillin, 100 μg/ml streptomycin, 10 μg/ml gentamycin, and 20 U/ml recombinant human IL-2 (R&D Systems, Inc). IL-2 is included in the culture medium to maintain the cell division initiated by the PHA mitogenic stimulation. PBMCs were maintained in this medium at a concentration of 1-2 x 10 ⁶ cells/mL with biweekly medium changes until used in the assay protocol. Cells were kept in culture for a maximum of two weeks before being deemed too old for use in assays and discarded. Monocytes were depleted from the culture as the result of adherence to the tissue culture flask.

For the standard PBMC assay, PHA-P stimulated cells from at least two normal donors were pooled (mixed together), diluted in fresh medium to a final concentration of 1 x 10 ⁶ cells/mL, and plated in the interior wells of a 96 well round bottom microplate at 50 μl/well (5 x 10 ⁴ cells/well) in a standard format developed by the Infectious Disease Research department of Southern Research Institute. Pooling (mixing) of mononuclear cells from more than one donor is used to minimize the variability observed between individual donors, which results from quantitative and qualitative differences in HIV infection and overall response to the PHA and IL-2 of primary lymphocyte populations. Each plate contains virus/cell control wells (cells plus virus), experimental wells (drug plus cells plus virus) and compound control wells (drug plus media without cells, necessary for MTS monitoring of cytotoxicity). Since HIV- 1 is not cytopathic to PBMCs, this allows the use of the same assay plate for both antiviral activity and cytotoxicity measurements. Test drug dilutions were prepared at a 2X concentration in microtiter tubes and 100 μl of each concentration was placed in appropriate wells using the standard format. 50 μl of a predetermined dilution of virus stock was placed in each test well (final MOI ~ 0.1 ). The PBMC cultures were maintained for seven days following infection at 37°C, 5% CO ₂. After this period, cell-free supernatant samples were collected for analysis of reverse transcriptase activity. Following removal of supernatant samples, compound cytotoxicity was measured by addition of MTS to the plates for determination of cell viability. Wells were also examined microscopically and any abnormalities were noted. MAGI

MAGI-R5 cells naturally express the CXCR4 co-receptor and are engineered to express CD4 (HIV-1 cell surface receptor), the CCR5 co-receptor and also to contain an LTR-β- galactosidase reporter construct. The MAGI Antiviral Assay is designed to identify compounds that block HIV-1 replication via targets in the viral life cycle up to and including Tat transactivation (e.g. virus attachment/fusion/entry, uncoating, reverse transcription, nuclear import, integration, LTR transactivation). MAGI cells are treated with compound for 15 to 30 min prior to addition of virus. HIV-1 is then added to the cells/compounds and the cultures are incubated for 48 hours. If the virus is able to infect the cells it will proceed through reverse transcription and integration and begin transcription from the integrated provirus. One of the first virus proteins produced is HIV 1 Tat, which transactivates the HIV-1 LTR promoter driving expression of β- galactosidase. As a result, infected cells begin to overproduce the β-galactosidase enzyme. Forty-eight hours post infection, the cells are lysed and β-galactosidase enzyme activity is measured using a chemiluminescence detection method (Perkin Elmer Applied Biosystems). Compound toxicity is monitored on replicate plates using MTS dye reduction (CellTiter 96® Reagent, Promega, Madison, Wl).

The invention accordingly shows that compounds of the general structure A and B inhibit the enzyme HIV-1 reverse transcriptase and thus have application as anti- HIV agents.

PCT/US2008/082531 claims the priority of USSN 60/986,990. However, at the time of filing this application, the priority document was not available from the US Patent Office. If the priority date of any compounds disclosed in PCT/US2008/082531 is later than the priority date of the compounds disclosed in this specification it will be necessary to amend the provisos. The following has therefore been included in this specification to provide for this eventuality.

The invention also provides the use of a compound selected from compounds of the formula A and B in the manufacture of a medicament for the treatment of a subject infected with HIV, a composition for use in treating a subject who has been infected with HIV, the composition including a compound selected from compounds of formula A or B, for use in the treatment of a subject suffering from an HIV infection, a method of treating a subject suffering from an HIV infection by administration of a compound selected from compounds of formula A or B and compounds of formula A or B in which, for formula A

R is selected from alkyl, branched alkyl, cycloalkyl, aryl, substituted aryl, naphthyl, benzyl and bicycloalkyl,

R ¹ is selected from alkyl, cycloalkyl, substituted alkyl, branched alkyl, phenyl, heteroaryl, oxacycloalkyl, bicycloalkyl, furyl, substituted furyl, thienyl and substituted thienyl

R ² - R ⁵ are independently selected from H, halogen, cyano, alkyl and substituted alkyl, or R ² and R ³ together form a carbocyclic ring or, independently, R ⁴ and R ⁵ together form a carbocyclic ring, R ⁶ is H, alkyl or alkanoyl, and in which for formula B,

R is cycloalkyl and R ¹ is substituted aryl provided that compounds disclosed in USSN 60/986,990 are excluded.

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