Triethylamine → HCID 86652732, compound

Participants

Reaction Steps

1,1′-Carbonyldiimidazole (227 mg, 1.4 mmol) was added to a solution of O-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yl) hydroxylamine (238 mg, 0.70 mmol) and triethylamine (141 mg, 1.4 mmol) in CH2Cl2 (6 ml) and stirred at room temperature for 17 hours. Cyclopropylmethanamine (75 mg, 1.05 mmol) was added to the reaction mixture and stirred at room temperature for another 7 hours. The reaction mixture was quenched with H2O (10 ml) and aqueous 1 N HCl solution (pH=3) and extracted with CH2Cl2 (70 ml×3). The combined organic phase was washed with aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/n-hexane: 33/67) to give 1-(cyclopropylmethyl)-3-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yloxy)urea (120 mg, 39%) as a white solid: LCMS: 438 [M+1]+. 1H NMR (DMSO-d6) δ: 0.14 (m, 2H), 0.35 (m, 2H), 0.90 (m, 1H), 1.74 (m, 2H), 1.86 (m, 2H), 2.85 (m, 4H), 3.20 (m, 2H), 3.65 (m, 1H), 6.71 (m, 1H), 7.65 (m, 2H), 7.90 (m, 2H), 8.86 (s, 1H).

Provenance & Evidence