Triethylamine → HCID 71116527, compound

Participants

Reaction Steps

1-(2,4-dichlorophenyl)-5-[4-(dimethylamino)phenyl]-4-methyl-1H-pyrazole-3-carboxylic acid (1 eq, 10 mg, 0.026 mmol), 4-hydroxy-4-phenylpiperidine (1 eq, 4.5 mg, 0.026 mmol), benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (1 eq., 11.3 mg, 0.026 mmol), and triethylamine (0.02 mL) were stirred in tetrahydrofuran (5 mL) for 16 h. 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-{[1-(2,4-dichlorophenyl)-5-[4-(dimethylamino)phenyl]-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-ol (7 mg, 50%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.73-1.95 (m, 2H) 2.09-2.29 (m, 5H) 2.85-3.04 (m, 3H) 3.34 (t, J=12.43 Hz, 1H) 3.66 (t, J=12.81 Hz, 1H) 4.34 (d, J=13.19 Hz, 1H) 4.74 (d, J=13.28 Hz, 1H) 6.61 (d, J=8.57 Hz, 2H) 6.99 (d, J=8.67 Hz, 2H) 7.09-7.57 (m, 8H).

Provenance & Evidence