Synthesis method of febuxostat decarboxylation impurity

A febuxostat and synthetic method technology, applied in the field of chemical pharmacy, can solve the problems of febuxostat with complex structural formula, many potential impurities in febuxostat API, long steps in the synthetic route, etc., and achieve high product yield and reliable Controllable, easy-to-operate effects

Inactive Publication Date: 2021-06-15
LANGFANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The structural formula of febuxostat is relatively complex, and the steps of the synthetic route are long, which leads to many potential impurities in febuxostat API

Method used

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  • Synthesis method of febuxostat decarboxylation impurity
  • Synthesis method of febuxostat decarboxylation impurity
  • Synthesis method of febuxostat decarboxylation impurity

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Embodiment Construction

[0024] Embodiments of the present invention will be further described below.

[0025] A kind of synthetic method of febuxostat decarboxylation impurity, reaction route is as follows:

[0026]

[0027] Among them, the specific content is as follows:

[0028] (1) Preparation of 2-(4-hydroxyphenyl)-4-methylthiazole:

[0029]

[0030] During the reaction, 2.26g of p-hydroxythiobenzamide and 15mL of absolute ethanol were placed in a 100mL three-necked flask, 2.42g of 1-chloroacetone was added under stirring, heated to reflux, and a solid was precipitated, reacted for 4 hours, TLC (chloroform: Ethanol=9:1) detection control reaction end point. After the reaction was completed, it was cooled and filtered to obtain 1.72 g of solid, with a yield of 99.5%.

[0031] (2) Preparation of 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole

[0032]

[0033] During the reaction, 1.71kg of 2-(4-hydroxyphenyl)-4-methylthiazole was placed in a 20L three-necked flask, 15L of trifluoroaceti...

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Abstract

The invention discloses a synthesis method of a febuxostat decarboxylation impurity, which comprises the following steps: by taking p-hydroxybenzenesulfamide as a raw material, carrying out reflux condensation on p-hydroxybenzenesulfamide and chloroacetone in ethanol, and carrying out hydroformylation, cyanation and alkylation on trifluoroacetic acid and urotropine, so as to obtain the febuxostat decarboxylation impurity with the reaction yield of more than 90% in each step. According to the synthesis method of the febuxostat decarboxylation impurity, the reaction steps are mild and controllable, the operation is simple, and the product purity reaches 99% or above.

Description

technical field [0001] The invention relates to the technical field of chemical pharmacy, in particular to a method for synthesizing febuxostat decarboxylation impurities. Background technique [0002] The chemical name of Febuxostat is 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid, which is a non-purine xanthine oxidase / xanthine A selective inhibitor of purine dehydrogenase (XO), with high selectivity and stronger activity, less adverse reactions, suitable for the treatment of chronic hyperuricemia and relief of gout, and its curative effect is better than that of allopurinol in the treatment of gout Effect. [0003] The structural formula of febuxostat is relatively complex, and the synthetic route has long steps, which leads to many potential impurities in febuxostat API. The synthesis of this series of impurity reference substances is of great significance to the quality research of febuxostat. Based on this, the present invention provides a synthet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/30G01N33/15
CPCC07D277/30G01N33/15
Inventor 孙玉琴杨卫民
Owner LANGFANG NORMAL UNIV
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