title: Synthesis and crystal structure of 6-fluoro-3-hydroxypyrazine-2-carboxamide.
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.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University.
authors.forename: Fangyuan
authors.initials: F
authors.lastname: Shi
authors.forename: Zongtao
authors.initials: Z
authors.lastname: Li
authors.forename: Lingjin
authors.initials: L
authors.lastname: Kong
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Xie
authors.forename: Tao
authors.initials: T
authors.lastname: Zhang
authors.forename: Wenfang
authors.initials: W
authors.lastname: Xu
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D006860:Hydrogen Bonding; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D011719:Pyrazines; C462182:favipiravir