Triethylamine → 1-[[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl]-4-phenyl-4-piperidinecarboxylic acid

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Reaction Steps

A 2 M solution of oxalyl chloride in dichloromethane (3 eq., 0.19 mL, 0.377 mmol) was added to 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (1 eq., 48 mg, 0.126 mmol) in dichloromethane (5 mL). Next, 2 drops of anhydrous N,N-dimethylformamide was added the reaction was stirred for 2 h. The reaction was concentrated in vacuo. The reaction mixture was dissolved in dichloromethane (5 mL). Triethylamine (3 eq., 0.05 mL, 0.377 mmol) and 4-carboxy-4-phenylpiperidin-1-ium chloride (1.5 eq., 45.7 mg, 0.189 mmol) was added and the reaction was stirred for 16 h. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-10% methanol/dichloromethane with 1% acetic acid to yield pure 1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidine-4-carboxylic acid (48 mg, 67%). (77) 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.87-2.09 (m, 2H) 2.15 (s, 3H) 2.61 (t, J=16.18 Hz, 2H) 3.21 (t, J=12.03 Hz, 1H) 3.47 (t, J=11.94 Hz, 1H) 4.26 (d, J=13.61 Hz, 1H) 4.57 (d, J=13.56 Hz, 1H) 7.05 (d, J=8.34 Hz, 2H) 7.12-7.45 (m, 10H).

Provenance & Evidence