Method for preparing high-yield and high-purity Iguratimod intermediate

An intermediate, methanesulfonamide technology, applied in the field of pharmaceutical preparation, can solve the problems of volatile, incomplete reaction, no purification steps, etc., and achieve the effects of easy industrial production, reduced environmental hazards, and good sample stability.
CN108586408AActive Publication Date: 2018-09-28YANGTZE RIVER PHARM GRP CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
YANGTZE RIVER PHARM GRP CO LTD
Publication Date
2018-09-28

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Abstract

The invention discloses a method for preparing an Iguratimod intermediate, i.e., 3-bromo-7-methsulfonamido-6-phenoxy-4H-1-benzo-2,3-dihydropyran-4-one. The method comprises the following steps: (1) dissolving cupric bromide in ethyl acetate and C1-C4 lower alkanol, and carrying out stirring for at least 30 minutes; (2) adding a dichloromethane solution of 7-sulfonamido-6-phenoxy-4H-1-benzo-2,3-dihydropyran-4-one into the solution obtained in the step (1), heating the temperature of the mixture to 20 DEG C to 50 DEG C with stirring, and performing a reaction for 2 to 6 hours; (3) carrying out filtering, washing filter liquor with an aqueous solution of sodium thiosulfate, and concentrating an organic phase, so as to obtain a crude product of the intermediate; and (4) carrying out refining with dichloromethane and petroleum ether, thereby obtaining a refined intermediate. The method is convenient in operation, high in conversion ratio and high in product purity, and the purity can reach96% or more.
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Description

technical field

[0001] The invention belongs to the field of medicine preparation, in particular, the invention relates to a high-yield and high-purity intermediate of iguratimod, namely 3-bromo-7-methanesulfonamide-6-phenoxy-4H-1-benzene The preparation method of -2,3-dihydropyran-4-one. Background technique

[0002] Iguratimod's generic name: Iguratimod, chemical name: N-[3-(formamido)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- Methanesulfonamide, English name: N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]-methanesulfona mide, is a therapeutic class developed by Japan Toyama Company Drugs for rheumatoid arthritis and osteoarthritis.

[0003] In the published materials, there are few reports on the preparation process of iguratimod. Basically, 4-chloro-3-nitroanisole is used as the starting material to prepare iguratimod through multi-step reactions. Wherein there are 3 routes using bromination reaction to prepare 3-bromo-7-methanesulfonamide-6-phenoxy-4H-1-benzo-...

Claims

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