Triethylamine → HCID 57343390, compound

Participants

Reaction Steps

Benzotriazole-1-yl-oxytris(dimethylamino)phosphonium-hexafluorophosphate (BOP) (1 eq, 490 mg, 1.11 mmol) was added to a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (1 eq, 422 mg, 1.11 mmol), tert-butyl 4-amino-1-piperidinecarboxylate (1 eq, 222 mg, 1.11 mmol), and triethylamine (3 eq., 0.46 mL, 3.32 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred 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 tert-butyl 4-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-amido]piperidine-1-carboxylate (548 mg, 88%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.33-1.51 (m, 9H) 1.93-2.10 (m, 2H) 2.37 (s, 3H) 2.91 (t, J=11.82 Hz, 2H) 3.89-4.23 (m, 2H) 6.84 (d, J=8.19 Hz, 1H) 7.00-7.12 (m, 2H) 7.19-7.36 (m, 4H) 7.43 (d, J=1.32 Hz, 1H).

Provenance & Evidence