title: An efficient preparation of vinamidinium hexafluorophosphate salts.
abstract: Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a-j in moderate to excellent recrystallized yields (28-90%). The cations are conveniently isolated as their hexafluorophosphate salts, which are easily handled nonhygroscopic solids. The nitro compound 3l is prepared in 91% yield by nitration of the parent vinamidinium 3k. The X-ray crystal structure is reported for the 2-phenyl isomer 3e and displays minimal overlap of the two pi-systems.
authors.affiliation: Department of Process Research, Merck & Co., Inc., Rahway, New Jersey 07065, USA. ian_davies1@merck.com
authors.forename: I W
authors.initials: IW
authors.lastname: Davies
authors.forename: J F
authors.initials: JF
authors.lastname: Marcoux
authors.forename: J
authors.initials: J
authors.lastname: Wu
authors.forename: M
authors.initials: M
authors.lastname: Palucki
authors.forename: E G
authors.initials: EG
authors.lastname: Corley
authors.forename: M A
authors.initials: MA
authors.lastname: Robbins
authors.forename: N
authors.initials: N
authors.lastname: Tsou
authors.forename: R G
authors.initials: RG
authors.lastname: Ball
authors.forename: P
authors.initials: P
authors.lastname: Dormer
authors.forename: R D
authors.initials: RD
authors.lastname: Larsen
authors.forename: P J
authors.initials: PJ
authors.lastname: Reider
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D018360:Crystallography, X-Ray; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D009566:Nitrates / Q000378:metabolism; D011437:Propylamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D007094:Imides; D009566:Nitrates; D011437:Propylamines