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Preparation method of arbidol intermediate

An intermediate and ethyl carboxylate technology, applied in the field of drug synthesis, can solve the problems of unavailable raw materials, cumbersome operation, and many "three wastes", and achieve the effect of cheap raw materials, easy operation, and easy availability of raw materials

Active Publication Date: 2020-06-12
SUZHOU JINGYE MEDICINE & CHEM
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0017] There are also some documents that describe the processes that are basically the same or similar to the processes listed above, and all have more or less disadvantages such as "three wastes", low yield, difficult raw materials, and cumbersome operations.

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  • Preparation method of arbidol intermediate
  • Preparation method of arbidol intermediate
  • Preparation method of arbidol intermediate

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Embodiment Construction

[0048] The specific implementation of the present invention will be further described below in conjunction with the examples. The following examples are only used to illustrate the technical solution of the present invention more clearly, but not to limit the protection scope of the present invention.

[0049] The present invention takes ethyl acetoacetate, monomethylamine and p-benzoquinone as starting materials, and prepares the target compound: 5-hydroxy-6-bromo-2- Ethyl phenylthiomethyl-1-methylindole-3-carboxylate;

[0050] The first step: ethyl acetoacetate is condensed with monomethylamine to obtain ethyl 3-methylamino-2-butenoate;

[0051] The second step: 3-methylamino-2-butenoic acid ethyl ester and p-benzoquinone ring synthesis to obtain 1,2-dimethyl-5-hydroxyl-1H-indole-3-carboxylic acid ethyl ester (hereinafter referred to as cyclization product);

[0052] The third step: the cyclization product is acylated with acetic anhydride to obtain ethyl 1,2-dimethyl-5-a...

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Abstract

The invention discloses a preparation method of an arbidol intermediate. Ethyl acetoacetate, monomethylamine and p-benzoquinone used as initial raw materials undergo methylation, cyclization, acetylation, bromination and benzene vulcanization to prepare the target compound ethyl 5-hydroxy-6-bromo-2-phenylthiomethyl-1-methylindole-3-carboxylate. The preparation method of the arbidol intermediate issimple and convenient to operate, cheap and easily available in raw materials, high in yield, low in cost, good in quality, environment-friendly, mild in reaction condition, high in safety productioncoefficient and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of an Arbidol intermediate. Background technique [0002] Arbidol hydrochloride (Arbidol) is an antiviral drug developed by the Medicinal Chemistry Research Center of the former Soviet Union. Its main indication is influenza caused by type A and type B influenza viruses. Also has antiviral activity. [0003] 6-bromo-5-hydroxyl-1-methyl-2-(phenylthiomethyl)indole-3-ethyl carboxylate is an important intermediate for the synthesis of Arbidol, and its structural formula is as follows: [0004] [0005] Molecular formula: C 19 h 18 BrNO 3 S; CAS No.: 131707-24-9. [0006] At present, the methods related to the synthetic method of 6-bromo-5-hydroxyl-1-methyl-2-(phenylthiomethyl) indole-3-formic acid ethyl ester mainly include: [0007] 1. Synthesis of Arbidol Hydrochloride China Journal of Pharmaceutical Industry 2017,48(1),30-32 [0008] Using 4-n...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/42
CPCC07D209/42
Inventor 沈建伟
Owner SUZHOU JINGYE MEDICINE & CHEM
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