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Method for preparing febuxostat intermediate

A compound and mixed acid technology, applied in the direction of organic chemistry, can solve the problems of many impurities in the reaction, difficult handling, low product yield, etc., and achieve the effect of mild reaction conditions, simple operation, and high yield

Active Publication Date: 2011-04-06
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] Using PPA (polyphosphoric acid) as the reaction solvent has the advantage of being cheap, but the reaction produces many impurities, which is difficult to handle and the product yield is low
[0018] Use trifluoroacetic acid as the reaction solvent, the reaction produces less impurities, and the product yield is high, but the price of trifluoroacetic acid is high, it is difficult to recycle, and the synthesis cost will be increased

Method used

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  • Method for preparing febuxostat intermediate
  • Method for preparing febuxostat intermediate
  • Method for preparing febuxostat intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 26.3g of ethyl 2-[4-hydroxyphenyl]-4-methylthiazole-5-carboxylate in 100ml of polyphosphoric acid and 40ml of concentrated hydrochloric acid, add 13g of urotropine, heat to 80°C and keep for 12 hours , the reaction solution was cooled to room temperature, and processed to obtain the product with a yield of 90%.

Embodiment 2

[0032] Dissolve 26.3g of ethyl 2-[4-hydroxyphenyl]-4-methylthiazole-5-carboxylate in 100ml of polyphosphoric acid and 50ml of concentrated sulfuric acid, add 12g of urotropine, heat to 80°C and keep for 12 hours , the reaction solution was cooled to room temperature and processed to obtain the product with a yield of 93%.

Embodiment 3

[0034] Dissolve 26.3g of ethyl 2-[4-hydroxyphenyl]-4-methylthiazole-5-carboxylate in 100ml of polyphosphoric acid and 40ml of phosphoric acid, add 10g of urotropine, heat to 120°C, and keep for 12 hours. The reaction solution was cooled to room temperature and processed to obtain the product with a yield of 70%.

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Abstract

The invention relates to a method for preparing a febuxostat intermediate, which comprises the following steps of: dissolving 2-[4-hydroxyphenyl]-4-methylthiazol-5-ethyl formate in a mixed acid reaction solvent, adding a certain amount of urotropine, heating to react for 1-36 h at certain temperature, and treating the reaction liquid to obtain corresponding heterocyclic aldehyde.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to the preparation of febuxostat intermediate 2-[3-formyl-4-hydroxyphenyl]-4-methylthiazole-5-carboxylic acid ethyl ester. Background technique [0002] Gout has become a common disease in the world today, especially among middle-aged and elderly men. The cause of the disease is that the body produces too much uric acid and the ability of the kidneys to clear it decreases, which leads to the continuous accumulation of uric acid in the body and the formation of hyperuricemia. The generation of uric acid in the body is related to purine metabolism. In the final stage of purine metabolism, xanthine generates uric acid under the action of xanthine oxidase (XO). Inhibiting the activity of XO can effectively reduce the generation of uric acid. Therefore, the new anti-gout drugs Development has always been a hot spot in drug research. . [0003] Febuxostat, whose chemical name is 2-[3-cya...

Claims

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Application Information

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IPC IPC(8): C07D277/56
Inventor 闫起强祁伟杨琰王文峰
Owner CHINA RESOURCES SAIKE PHARMA
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