Triethylamine → HCID 57342713, compound

Participants

Reaction Steps

1-{[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidine-4-carboxylic acid (1 eq., 12.7 mg, 0.024 mmol), ammonium chloride (10 eq., 12.7 mg, 0.24 mmol), benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (1 eq, 10.5 mg, 0.024 mmol), and triethylamine (10.1 eq., 0.03 mL, 0.024 mmol) was stirred in tetrahydrofuran (5 mL) for 3 d. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% ethyl acetate/hexane to yield pure 1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidine-4-carboxamide (6 mg, 44%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.92-2.31 (m, 5H) 2.46 (d, J=13.94 Hz, 2H) 3.65 (t, J=10.36 Hz, 1H) 3.75-3.90 (m, 1H) 4.02 (d, J=13.38 Hz, 1H) 4.23 (d, J=13.00 Hz, 1H) 5.24 (br. s., 2H) 7.07 (d, J=8.38 Hz, 2H) 7.12-7.20 (m, 1H) 7.20-7.49 (m, 9H).

Provenance & Evidence