Propylamine → HCID 58235432, compound

Participants

Reaction Steps

1,1′-Carbonyldiimidazole (162 mg, 1.00 mmol) was added to a solution of (S)—O-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yl)hydroxyl amine (155 mg, 0.50 mmol) and triethylamine (101 mg, 1.00 mmol) in CH2Cl2 (15 ml) and stirred at room temperature for 24 hours. Propan-1-amine (35.0 mg, 0.60 mmol) was added to the reaction mixture and stirred at room temperature for another 17 hours. The reaction mixture was washed with aqueous 0.1 N HCl solution (15 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: 50/50) to give (S)-1-propyl-3-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yloxy)urea (120 mg, 61%) as pale yellow oil: LCMS: 396 [M+1]+. 1H NMR (DMSO-d6) δ: 0.76-0.81 (3H, t), 1.34-1.41 (2H, m), 1.77-1.83 (1H, m), 2.01-2.06 (1H, m), 2.90-2.97 (2H, m), 3.16-3.28 (3H, m), 3.50-3.54 (1H, d), 4.22 (1H, s), 6.64-6.68 (1H, t), 7.83-7.89 (1H, t), 8.01 (1H, s), 8.07-8.13 (1H, t), 8.92 (1H, s).

Provenance & Evidence