An efficient preparation of vinamidinium hexafluorophosphate salts.
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.
Davies
I W
IW
Department of Process Research, Merck & Co., Inc., Rahway, New Jersey 07065, USA. ian_davies1@merck.com
Marcoux
J F
JF
Wu
J
J
Palucki
M
M
Corley
E G
EG
Robbins
M A
MA
Tsou
N
N
Ball
R G
RG
Dormer
P
P
Larsen
R D
RD
Reider
P J
PJ
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
D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D007094:Imides; D009566:Nitrates; D011437:Propylamines