Production method of iguratimod intermediate

A production method and intermediate technology, applied in the production field of Alamod intermediates, can solve the problems of high cost and environmental protection requirements, incomplete reaction, difficult removal of impurities, etc., to achieve low production cost and high product purity Improve and reduce the effect of reaction impurities

Inactive Publication Date: 2021-02-19
WUDI REACTION PHARMA & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] N-(7-(methylsulfonamide O)-4-oxo-6-phenoxy-4H-benzopyran-3-yl)formamide; N-[3-(formamido)-4 -Oxy-6-phenoxy-4H-1-benzopyran-7-yl]methanesulfonamide is a key intermediate in the synthesis of drug iguratimod, due to the small amount of water contained in the acetone used in the production process The pivaloyl chloride is decomposed, and impurities are produced during the reaction proces

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]Add 27kg of acetone and 1kg of sodium carbonate, 6kg of pivaloyl chloride, and 1kg of sodium formate into a 100L reactor. After stirring and cooling to 20-25℃, add 5.6kg of aminoacetonitrile hydrochloride. After reacting for 5 hours, add 10kg of water, and a large amount of white precipitates. Solid, suction filtered product, yield 85%.

Embodiment 2

[0019]Add 27kg of acetone and 1kg of sodium carbonate to a 100L reactor, add 6kg of pivaloyl chloride dropwise at 20-25℃, react for two hours, add 1kg of sodium formate, add 5.6kg of aminoacetonitrile hydrochloride after controlling the temperature at 20-25℃, and react After 5 hours, 10kg of water was added, and a large amount of white solid was precipitated. The product was suction filtered with a yield of 90%; compared with Example 1, this example can improve the product yield by controlling the dropping temperature.

Embodiment 3

[0021]Add 27kg of acetone and 1kg of sodium carbonate to a 100L reactor, start stirring and add 6kg of pivaloyl chloride dropwise, react for two hours, add 1kg of sodium formate and stir for 4 hours, control the temperature at 20-25℃ and add 5.6kg of aminoacetonitrile hydrochloride. After reacting for 5 hours, 10kg of water was added to precipitate a large amount of white solids. The product was filtered by suction with a yield of 94%. Compared with Examples 1 and 2, this example can further improve by controlling the dropping temperature and the treatment of acylate. Improve the yield of the product to meet the requirements.

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PUM

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Abstract

The invention discloses a production method of an iguratimod intermediate, which comprises the following steps: S1, by using alpha-amino-2-methoxy-4-methanesulfonylamino-5-phenoxy acetophenone hydrochloride as a starting raw material, selecting a 100L reaction kettle, and adding 27kg of acetone and 1kg of sodium carbonate into the reaction kettle, wherein pivaloyl chloride is taken as an acylatingagent. The preparation method is simple in process and low in production cost, that is, sodium carbonate is added into the reaction raw material to generate impurities in the reaction process of pivaloyl chloride and sodium formate to generate sodium salt, so that the impurities cannot continuously react with alpha-amino-2-methoxy-4-methanesulfonylamino-5-phenoxy acetophenone hydrochloride, the generation of reaction impurities is reduced, the purity of the product is improved, the product is not refined to obtain a target product, and the yield is 85-95%.

Description

Technical field[0001]The present invention relates to the technical field of medicine, in particular to a production method of Iramod intermediate.Background technique[0002]Iramod is a new type of disease-relieving medicine for the treatment of rheumatoid arthritis and osteoarthritis jointly developed by Japan's Toyama Yu Eisai Pharmaceutical Company. Compared with other drugs, its characteristics are rapid and effective, and its efficacy is equivalent to that of highly effective antirheumatic drugs, but its toxicity is lower.[0003]N-(7-(Methylsulfonamide O)-4-oxo-6-phenoxy-4H-benzopyran-3-yl)carboxamide; N-[3-(carboxamido)-4 -Oxy-6-phenoxy-4H-1-benzopyran-7-yl]methanesulfonamide is a key intermediate in the synthesis of ilamod, due to the small amount of water contained in the acetone used in the production process Pivaloyl chloride is decomposed, and impurities are generated in the reaction process. The raw materials continue to react to form impurities that are not easy to remove...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C303/44C07C311/08
CPCC07C303/40C07C303/44
Inventor 徐承环巩春浩马红建
Owner WUDI REACTION PHARMA & CHEM
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