Process for preparing ethyl 6-bromo-5-hydroxy-4-...

C - Chemistry – Metallurgy – 07 – D

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C07D 209/42 (2006.01) A61K 31/405 (2006.01) E04B 1/32 (2006.01)

Patent

CA 2008911

A process for preparing a novel compound - ethyl 6-bromo-5- hydroxy-4-dimethylaminomethyl-1-methyl-2-phenyl-thiomethyl- 3-carboxylate hydrochloride monohydrate of the following formula: Image involves treating ethyl 5-acetoxy-1,2-dimethylindole-3-car- boxylate with a brominating agent in an inert organic sol- vent under reflux, reacting the resultant ethyl 5-acetoxy-6- bromo-2-bromomethyl-1-methylindole-3-carboxylate to react with thiophenol in the presence of an alkali metal hydroxide or its alcoholate in an organic solvent, reacting the resultant ethyl 6-bromo-5-hydroxy-1-methyl-2-phenyl- thiomethylindole-3-carboxylate with an aminomethylating agent in an organic solvent at a temperature from 65° to a temperature of refluxing the reaction mixture. The end product is then isolated from the resultant base-ethyl 6- bromo-5-hydroxy-4-dimethylaminomethyl-1-2-phenylthiomet- hylindole-3-carboxylate. The compound according to the invention is an active principle of a pharmaceutical preparation having the antiviral, immunomodulatory and inerferon-inducing effect.

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