Title:
PREPARATION METHOD FOR 3-SUBSTITUTED-9-METHYL-THIENO-TRIAZOLOOXAZINE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/123655
Kind Code:
A1
Abstract:
The present invention relates to a preparation method for a 3-substituted-9-methyl-thieno-triazolooxazine compound, and overcomes the defects of long route (14 steps), low yield and low atom economy in the prior art. In the present invention, initial raw materials which are easily available and cheap are used, the route is simple, multiple steps can be continuously carried out without the need for post-treatment and purification, and the reaction yield is high, thereby improving the overall yield and atom economy of the route. Especially step 9, a one-step method is carried out for deprotection and a cyclization reaction, such that the problem of substituting benzyl chloride with fluorine in a substrate structure when TBAF is used to remove TBDPS protective group in the prior art is solved, and in addition, the problems of by-products being difficult to purify and the yield being reduced are effectively solved. In addition, the synthesis method provided in the present invention has mild reaction conditions, a simple and convenient operation method, and good reproducibility, and not only is suitable for laboratory preparation in a small amount, but is also suitable for industrial large-scale production.
Inventors:
SUN XIAO (CN)
ZHANG HONGWEI (CN)
ZHOU ZHIGUO (CN)
GAO QIANG (CN)
ZHENG BAOFU (CN)
ZHANG HONGWEI (CN)
ZHOU ZHIGUO (CN)
GAO QIANG (CN)
ZHENG BAOFU (CN)
Application Number:
PCT/CN2022/079070
Publication Date:
July 06, 2023
Filing Date:
March 03, 2022
Export Citation:
Assignee:
SHANGHAI HAOYUAN MEDCHEMEXPRESS CO LTD (CN)
International Classes:
C07D498/14
Domestic Patent References:
| WO2019055444A1 | 2019-03-21 |
Foreign References:
| CN110062759A | 2019-07-26 | |||
| CN109071562A | 2018-12-21 | |||
| US20030073733A1 | 2003-04-17 |
Other References:
CHONG QIN, YANG HU, BING ZHOU, ESTER FERNANDEZ-SALAS, CHAO-YIE YANG, LIU LIU, DONNA MCEACHERN, SALLY PRZYBRANOWSKI, MI WANG, JEANN: "Discovery of QCA570 as an Exceptionally Potent and Efficacious Proteolysis Targeting Chimera (PROTAC) Degrader of the Bromodomain and Extra-Terminal (BET) Proteins Capable of Inducing Complete and Durable Tumor Regression", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 61, no. 15, 9 August 2018 (2018-08-09), US , pages 6685 - 6704, XP055522768, ISSN: 0022-2623, DOI: 10.1021/acs.jmedchem.8b00506
Attorney, Agent or Firm:
PATENTSINO IP FIRM (CN)
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