1-Aminopiperidine → HCID 11294616, compound

Participants

Reaction Steps

Part D: 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-fluoromethyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide. 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-fluoromethyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide was obtained by reacting 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-fluoromethyl-1H-imidazole-4-carboxylic acid (0.87 g, 2.18 mmol), diisopropylethylamine (DIPEA) (0.84 mL, 4.80 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (0.99 g, 2.62 mmol) and 1-aminopiperidine (0.28 mL, 2.62 mmol) for 16 hours at room temperature. The resulting mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate, successively washed with aqueous NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated to give a crude solid. This solid was further purified by flash chromatography. 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-fluoromethyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide was obtained in 64% yield, mp 162–163° C.; 1H-NMR (600 MHz, DMSO-d6) δ 1.35–1.41 (m, 2H), 1.61–1.66 (m, 4H), 2.80–2.84 (m, 4H), 5.63 (d, J=48 Hz, 2H), 7.36 (d, J=8 Hz, 2H), 7.44 (dd, J=8 and 2 Hz, 1H), 7.48 (d, J=8 Hz, 2H), 7.55 (d, J=2 Hz, 1H), 7.67 (d, J=8 Hz, 1H), 9.10 (s, 1H); HRMS (C22H21Cl3FN4O) [M+H]+: found m/z 481.0760, calcd 481.0765.

Provenance & Evidence