Hydroxylamine → HCID 86709283, compound

Participants

Reaction Conditions

Reaction Steps

To s solution of 1-[3-fluoro-4-[[(3S)-3-methyl-1,1-dioxo-6-phenyl-thiazinan-2-yl]methyl]phenyl]-piperidine-4-carbonitrile Stereoisomer A (1.37 g, 3.12 mmol, prepared as described in Example 5) in ethanol (15 mL) was added hydroxylamine (50 mass % in water, 0.29 mL, 9.4 mmol) and the reaction was stirred at 60° C. for 2 hours. The solution was concentrated and purified by preparative HPLC to give 1-[3-fluoro-4-[[(3S,6R)-3-methyl-1,1-dioxo-6-phenyl-thiazinan-2-yl]methyl]phenyl]-N′-hydroxy-piperidine-4-carboxamidine Stereoisomer A (1.1 g, 75% yield) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.82-8.76 (s, 1H), 7.48-7.43 (m, 2H), 7.42-7.33 (m, 3H), 7.32-7.26 (m, 1H), 6.82-6.76 (m, 1H), 6.72-6.65 (m, 1H), 5.36-5.26 (s, 2H), 4.49-4.42 (m, 1H), 4.42-4.36 (m, 1H), 4.31-4.23 (m, 1H), 4.15-4.01 (m, 1H), 3.80-3.67 (m, 2H), 2.72-2.59 (m, 2H), 2.46-2.36 (m, 1H), 2.21-2.04 (m, 2H), 1.84-1.74 (m, 3H), 1.73-1.57 (m, 3H), 1.12-1.04 (d, J=6.8 Hz, 3H); LCMS [M+1]+=475.2.

Provenance & Evidence