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Preparation method of iguratimod intermediate

A technology for intermediates and solids, applied in the field of preparation of Ailamod intermediates, can solve the problems of lengthy steps and unfavorable industrial production.

Inactive Publication Date: 2017-08-08
常州佳德医药科技有限公司
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Problems solved by technology

[0005] The original process uses 4-chloro-3-nitroanisole (compound 1) as raw material, undergoes etherification, demethylation, reduction of iron powder, mesylation, alkoxylation, and Friedel-Craftsization to obtain the desired Intermediate (Xinai Ⅳ), and then dehydrogenation, halogenation, amination and formylation to obtain iguratimod (T-164), the steps are tedious and unfavorable for industrial production

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  • Preparation method of iguratimod intermediate
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  • Preparation method of iguratimod intermediate

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Embodiment Construction

[0026] The present invention will be further described below in conjunction with the embodiments and the accompanying drawings.

[0027] (1) Etherification: Take 20g of 4-chloro-3-nitroanisole in a 150mL reaction bottle, add 12g of phenol, 14g of potassium tert-butoxide, and 80mL of DMF, stir mechanically and raise the temperature to an internal temperature of 110°C, and keep the temperature for 4h Afterwards, TLC (developer EA:PE=1:10) sampling has been completely reacted, cooled to room temperature and poured into a 500mL large beaker filled with 100mL water, added 150mL of ethyl acetate to extract three times, combined the organic layer, and washed the organic layer with 2N hydrochloric acid. layer until pH = 3, dried and concentrated the organic layer to obtain 25 g of a reddish-brown oil (compound 2, HPLC: 91%).

[0028] (2) Reduction: Take 20g of compound 2 in a 150mL reaction flask, add 80% hydrazine hydrate 8g, ferric chloride 0.3g, ethanol 50mL, mechanically stir and ...

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Abstract

The invention discloses a preparation method of an iguratimod intermediate (novel iguratimod IV). The preparation method is characterized in that the optimization is performed on the original process; 4-chloro-3-nitroanisole (compound I) is used as raw materials; through etherification, hydrazine hydrate reduction, methyl sulfonylation and friedel-crafts reaction, the target product (the novel iguratimod IV) can be directly obtained. The steps of demethylation and oxyalkylation are eliminated; the effects of simplifying the process and improving the yield are achieved; the industrial production is facilitated. Through the process, 6-step reaction is changed to 4-step reaction; the synthesis steps are shortened; finally, the obtained product purity reaches up to 99 percent; the total mol yield is 54 percent.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, in particular to a preparation method of an iguratimod intermediate (Xinai IV). Background technique [0002] Iguratimod (T-614) is an unmarketed non-steroidal anti-inflammatory drug (NSAIDs), chemical name 3-formamido-7-methanesulfonyl-6-phenoxy-4H-1- Benzopyran-4-one is a new type of disease-modifying drug (DMARDs) for the treatment of rheumatoid arthritis (RA) and osteoarthritis (OA) jointly developed by Toyama and Eisai Pharmaceutical Co., Ltd. . Compared with the previous DMARDs, its characteristic is markedly effective, and its curative effect is equal to that of highly effective antirheumatic drugs (SAP, MTX), but its toxicity is low. [0003] 3-Methanesulfonamide-4-phenoxy-6-acetylanisole (Xinai Ⅳ) is an important intermediate in the synthesis process of iguratimod. [0004] [0005] The original process uses 4-chloro-3-nitroanisole (compound 1) as a raw material, un...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/08
CPCC07C303/40C07C201/12C07C213/02C07C303/38C07C311/08C07C217/90C07C205/38
Inventor 韩冰冰
Owner 常州佳德医药科技有限公司
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