Synthesis and crystal structure of 6-fluoro-3-hydroxypyrazine-2-carboxamide

Drug Discov Ther. 2014 Jun;8(3):117-20. doi: 10.5582/ddt.2014.01028.

Abstract

As a RNA polymerase inhibitor, 6-fluoro-3-hydroxypyrazine-2-carboxamide commercially named favipiravir has been proved to have potent inhibitory activity against RNA viruses in vitro and in vivo. A four-step synthesis of the compound is described in this article, amidation, nitrification, reduction and fluorination with an overall yield of about 8%. In addition, we reported the crystal structure of the title compound. The molecule is almost planar and the intramolecular O-H(•••)O hydrogen bond makes a 6-member ring. In the crystal, molecules are packing governed by both hydrogen bonds and stacking interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Crystallization
  • Hydrogen Bonding
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry

Substances

  • Amides
  • Pyrazines
  • favipiravir