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Favipiravir synthesis method

A synthesis method and favipiravir technology, applied in organic chemistry and other directions, can solve problems such as difficult industrial production, and achieve the effects of mild conditions, simple raw materials, and good industrial value.

Inactive Publication Date: 2017-10-03
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] As can be seen from the above, there are still many technical problems in the existing synthetic methods, which are difficult to be applicable to industrialized production

Method used

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Embodiment Construction

[0036] The following clearly and completely describes the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only some of the embodiments of the present invention, but not all of them. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.

[0037] In the embodiment of the present invention, a synthetic method of Favipiravir:

[0038] 1) Preparation of 1.4-dioxypyrazinamide (2): Control the temperature at -5 to 5°C, mix 5.25 g of 2-cyanopyrazine (1) with 29.95 g of glacial acetic acid and 45.30 g of 30% hydrogen peroxide, Heat up to 95°C, reflux for 22 hours, TLC shows no raw material, 40°C vacuum rotary evaporation to remove the solvent, add 15ml of water, vacuum rotary evaporation, repeat several times to remove glacial acetic acid, add 15ml of water, add hot chlorofo...

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Abstract

The invention discloses a favipiravir synthesis method, which comprises the following steps that (1) a pyrazine compound is dissolved in an organic reagent I; nitrogen oxidation reaction is performed to obtain white solid matters; (2) the white solid matters of pyrazine dinitrogen oxides are added into an organic reagent II to perform chlorination reaction; light yellow solids are obtained; (3) the obtained light yellow solids, a dry aprotic polar solvent, a dry fluorion donor reagent and tetrabutylammonium bromide are uniformly mixed; stirring reaction is performed to obtain light yellow solids; (4) the prepared 3,6-dichloropyrazine-2-formonitrile and a fluorizating agent perform aromatic ring fluoronation; (5) hexafluoro reaction products are directly catalyzed through hydrogen peroxide; cyan-hydrolysis reaction is performed; (6) cyan-hydrolysis reaction products are directly catalyzed through an aqueous alkaline solution; aromatic ring hydroxyl substitution reaction is performed; then, through purification treatment, favipiravir is prepared. The method disclosed by the invention has the advantages that the raw materials are simple and are easily to obtain; the synthesis process is simple; good industrial value is realized; green and environment-friendly effects are achieved.

Description

technical field [0001] The invention relates to a synthetic method of Favipiravir. Background technique [0002] Favipiravir (favipiravir), the chemical name is 6-fluoro-3-hydroxypyrazine-2-carboxamide, and the molecular formula is: C 5 h 4 N 3 o 2 F, molecular weight: 157.1, has the following structural formula: [0003] [0004] Favipiravir was researched and developed by Toyama Chemical Co., Ltd. in Japan. In 2011, it completed phase III clinical trials in Japan. It was approved for marketing in 2014. It is mainly used for the treatment of influenza clinically. It is a wide range of RNA-dependent RNA polymerase inhibitors. Spectrum antiviral drugs. Studies have shown that Favipiravir forms Favipiravir-ribofuranosyl-5-triphosphate (T-705RTP) under the action of intracellular enzymes, which competitively inhibits viral RNA-dependent RNA polymerase, thereby inhibiting the viral genome Replication and transcription; at the same time, it can also be immersed in viral ...

Claims

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Application Information

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IPC IPC(8): C07D241/24
CPCC07D241/24
Inventor 李孟阳
Owner ZHENGZHOU UNIV
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