Triethylamine → HCID 86716055, compound

Participants

Reaction Steps

To 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (1 eq, 200 mg, 0.52 mmol), tert-butyl 4-piperidinylcarbamate (1 eq, 105 mg, 0.052 mmol), and triethylamine (3 eq, 0.22 mL, 1.57 mmol) was added (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (1 eq, 232 mg, 0.52 mmol). The reaction was stirred 16 h and then concentrated in vacuo. The crude material was purified by column chromatography 0-100% ethyl acetate/hexanes to yield 277 mg (93%) of desired product. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.45 (s, 11H) 1.95-2.10 (m, 2H) 2.14-2.25 (m, 3H) 2.97 (br. s., 1H) 3.25 (d, J=7.63 Hz, 1H) 3.66-3.82 (m, 1H) 4.31 (d, J=13.37 Hz, 1H) 4.49 (d, J=5.84 Hz, 1H) 4.66 (d, J=13.09 Hz, 1H) 7.03-7.10 (m, 2H) 7.12-7.18 (m, 1H) 7.21-7.34 (m, 3H) 7.45 (d, J=2.07 Hz, 1H); [M+Na]+ 587.4.

Provenance & Evidence