A kind of new synthetic method of dasatinib

A synthetic method, dasatinib technology, applied in the field of medicinal chemistry, can solve the problems of high volatility, unsuitable for purchase, difficult to store, etc., and achieve the effect of simple separation, convenient industrial production, and few synthetic steps

Active Publication Date: 2017-07-04
CHANGZHOU RUIBO BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0017] Route 3 is somewhat similar to route 4. The raw material 2-methyl-4-amino-6-chloropyrimidine used in route 3 is relatively expensive and not suitable for purchase; although route 4 uses cheap 4,6-dichloro-2- Methylpyrimidine replaced 2-methyl-4-amino-6-chloropyrimidine, and thiourea replaced the more expensive ethyl isothiocyanatoformate, but the starting material (E) used in the two routes -3-Ethoxyacryloyl chloride is highly volatile and difficult to store; to prepare this raw material by yourself, you need to use dangerous vinyl ether as the starting material to react with triphosgene, which is not very conducive to industrial production

Method used

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  • A kind of new synthetic method of dasatinib
  • A kind of new synthetic method of dasatinib
  • A kind of new synthetic method of dasatinib

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Embodiment Construction

[0027] In order to make the technical means, creative features, work flow, and use methods of the present invention achieve the purpose and effect easy to understand, the present invention will be further elaborated below in conjunction with specific reaction formulas.

[0028]

[0029] Synthesis of compound II:

[0030] Add 44 grams of 60% sodium hydride (1.10mol) and 1200 milliliters of methyl tert-butyl ether in the reaction flask, stir, cool to 0-5 ° C, dropwise add 122.5 grams of ethyl chloroacetate (1.00mol) and 74 grams Ethyl formate (1.00mol), temperature control below 5 ℃, after the dropwise addition, naturally return to room temperature and react overnight; Extract the aqueous layer with ether; combine the organic phases, concentrate and recover the solvent; add hydrochloric acid to the aqueous phase to adjust the pH=3-4, add 60.8 grams of thiourea (0.80 mol), and reflux for 2 hours. After the reaction, the reaction solution is cooled to 50 ° C. Add 75 grams of a...

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Abstract

The invention discloses a novel synthetic method of dasatinib. The method has few steps and simple operation, uses cheap and easily obtained raw materials, and is applicable to industrialized production.

Description

[0001] Technical field: [0002] The invention relates to the field of medicinal chemistry, in particular to a new synthesis method of Dasatinib. [0003] Background technique: [0004] Dasatinib (Dasatinib) trade name is SPRYCEL TM , the chemical name is N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4- Pyrimidinyl]-amino]-5-thiazole carboxamide is an oral multiple tyrosine kinase inhibitor developed by Bristol-Myers Squibb, the inhibited kinases include Bcr-Ab1, Src kinase family, c-Kit and PDGFR- β etc. Dasatinib monohydrate passed the priority approval of the US FDA in 2006. It is clinically used for the treatment of chronic myeloid leukemia and also for the treatment of benign Philadelphia-stained acute lymphoblastic leukemia. This product has inhibitory effects on various mutants of Bcr-Ab1 kinase, and the inhibitory intensity is much higher than that of Imatinib, and no drug resistance has been found. [0005] [0006] Regarding the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12
CPCC07D417/12
Inventor 魏峰吴宗铨葛二鹏
Owner CHANGZHOU RUIBO BIO TECH
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