Pyridine → HCID 58235348, compound

Participants

Reaction Steps

Isocyanatoethane (36.0 mg, 0.5 mmol) was added to a solution of (S)—O-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yl)hydroxyl amine (155 mg, 0.5 mmol) and pyridine (119 mg, 1.5 mmol) in CH2Cl2 (8 ml), and the whole was stirred at room temperature for 17 hours. The reaction mixture was washed with aqueous 0.1 N HCl solution (10 ml), H2O (20 ml×3) and brine (20 ml), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/petroleum ether: 60/40) to give (S)-1-ethyl-3-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yloxy)urea (150 mg, 64%) as pale yellow oil: LCMS: 382 [M+1]+. 1H NMR (DMSO-d6) δ: 0.95-1.00 (3H, t), 1.74-1.84 (1H, M), 2.05-2.06 (1H, m), 2.99-3.04 (2H, m), 3.15-3.31 (3H, m), 3.50-3.54 (1H, d), 4.21 (1H, s), 6.66-6.70 (1H, t), 7.84-7.89 (1H, t), 8.01 (1H, s), 8.07-8.14 (1H, t), 8.92 (1H, s).

Provenance & Evidence