Triethylamine → HCID 44176498, compound

Participants

Reaction Steps

To a solution of 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazole-4-carbohydrazide (216 mg, 0.432 mmol), triethylamine (0.132 mL, 0.949 mmol) in 1 mL anhydrous THF was added carbonyldiimidazole (140 mg, 0.864 mmol). The reaction was stirred for 24 h at room temperature. The reaction was diluted with ethyl acetate, washed with water, brine, and dried with MgSO4. The residue was absorbed onto silica and purified by column chromatography using hexanes:ethyl acetate as eluents to afford 5-(1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)-1,3,4-oxadiazol-2(3H)-one (120 mgs, 52%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 12.48 (s, 1H), 8.39 (s, 1H), 8.15-8.14 (m, 1H), 8.04-8.01 (m, 1H), 7.93-7.90 (m, 1H) 7.87-7.82 (m, 3H), 7.75-7.70 (m, 3H), 7.66-7.64 (m, 1H), 7.38 (d, J=8.61 Hz, 2H), 3.28 (s, 3H); MS (ES): 527.3 [M+H]+ and 549.3 [M+Na]+.

Provenance & Evidence