Triethylamine → HCID 57342714, compound

Participants

Reaction Steps

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carb oxylic acid (1 eq, 20 mg, 0.052 mmol), triethylamine (3 eq, 0.02 mL, 0.157 mmol), 4-(ethylamino)-4-piperidinecarboxamide (1 eq, 9 mg, 0.052 mmol), and benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (1 eq, 23 mg, 0.052 mmol) was 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% CMA 80/ethyl acetate and precipitated from ethyl acetate with hexane to yield pure 1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-(ethylamino)piperidine-4-carboxamide (13 mg, 46%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.10 (t, J=6.97 Hz, 3H) 1.61-1.80 (m, 2H) 2.08-2.26 (m, 5H) 2.45-2.63 (m, 2H) 3.68 (td, J=8.85, 4.43 Hz, 2H) 3.96-4.19 (m, 2H) 5.40 (br. s., 1H) 7.07 (d, J=8.29 Hz, 2H) 7.12-7.19 (m, 1H) 7.20-7.36 (m, 3H) 7.44 (d, J=1.98 Hz, 1H).

Provenance & Evidence