Pyridine → HCID 57504946, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-((4aR,6R,7aS)-6-hydroxy-7a-(3′-methoxybiphenyl-3-yl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl)benzamide (0.061 g, 0.133 mmol), o-methylhydroxylamine hydrochloride (0.111 g, 1.3 mmol) and pyridine (0.105 g, 1.30 mmol) in ethanol (5 mL) is heated to 50° C. for 15 h. The mixture is concentrated under reduced pressure. The crude product is purified by silica gel chromatography eluting with 0.5% to 10% NH3 (7 N solution in methanol) in dichloromethane over 30 minutes to afford the title compound as a freebase (0.041 g, 87%). ES/MS m/e: 355 (M+1). A 1 N solution of HCl in Et2O (0.139 mL, 0.139 mmol) is added to a solution of (4aR,6R,7aS)-2-amino-7a-(3′-methoxybiphenyl-3-yl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-6-ol (0.041 g, 0.116 mmol) in minimal dichloromethane and methanol. The solvent is removed under reduced pressure to give the title compound (0.045 g, 86%). ES/MS m/e: 355 (M+1).

Provenance & Evidence