1,2-Dichloroethane → HCID 86731023, compound

Participants

Reaction Steps

To a solution of the crude acid (1S,3S,4S and 1R,3R,4R)-4-[4-carbamoyl-3-[(4-chlorophenyl)amino]-1H-pyrazol-1-yl]-3-cyanocyclohexane-1-carboxylic acid (Example #35-1 Step C, 500 mg, 1.3 mmol) in MeOH (5 mL) were sequentially added EDC (324 mg, 1.7 mmol) and HOBt (210 mg, 1.6 mmol). The resulting solution was stirred at ambient temperature overnight before it was concentrated in vacuo. The crude residue was partitioned between DCM (20 mL) and water (5 mL). The organic solution was washed with saturated aqueous NaHCO3 (2×5 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 2-4% MeOH/DCM) to afford the title compound. 1H NMR (400 MHz, CD3OD) δ 8.13 (s, 1H), 7.55 (d, J=8.8 Hz, 2H), 7.24 (d, J=9.2 Hz, 2H), 4.35-4.28 (m, 1H), 3.74 (s, 3H), 3.52-3.34 (m, 1H), 2.68-2.62 (m, 1H), 2.55-2.52 (m, 1H), 2.24-2.16 (m, 3H), 2.00-1.90 (m, 1H), 1.73-1.70 (m, 1H). MS ESI: [M+H]+ m/z 401.

Provenance & Evidence