Hydrochloric Acid → HCID 118566573, compound

Participants

Reaction Steps

To a stirred solution of 4-{6-chloro-5-[(4,4-difluoro-cyclohexylmethyl)-carbamoyl]-quinolin-2-yl}-piperidine-1-carboxylic acid tert-butyl ester (50 mg, 0.09 mmol, 1.00 eq) in dichloromethane (5.00 mL, 77.14 mmol, 100 V) at 0 OC was added 4M HCl in dioxane (2 mL, 8.00 mmol, 89.05 eq) dropwise under nitrogen. The reaction mixture was stirred at RT for 2 h and the solvent was evaporated completely. The crude obtained was basified with 10% sodium bicarbonate solution and was extracted with DCM. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The crude obtained was purified by preparative HPLC to afford the title compound (10 mg, 0.02 mmol, 24.5%) as a pale brown solid. 1H NMR (400 MHz, DMSO-d6): δ 8.79 (t, J=5.91 Hz, 1H), 7.99 (dd, J=9.42, 9.0 Hz, 2H), 7.76 (d, J=9.03 Hz, 1H), 7.58 (d, J=8.72 Hz, 1H), 3.43 (s, 1H), 3.25-3.29 (m, 2H), 3.03-3.06 (m, 2H), 2.91-2.98 (m, 1H), 2.58-2.67 (m, 2H), 2.02-2.04 (m, 2H), 1.64-1.84 (m, 9H), 1.23-1.30 (m, 2H). m/z: 422.0 [M+H]+

Provenance & Evidence