1-Hydroxybenzotriazole → N-Carbamoylmethyl-1'-{[3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-4-oxospiro[chroman-2,4'-piperidine]-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-Carbamoylmethyl-4-oxospiro[chroman-2,4′-piperidine]-6-carboxamide hydrochloride (354 mg), 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (145 mg), WSC hydrochloride (115 mg), HOBT (91.2 mg) and triethylamine (0.209 mL) were suspended in DMF (3 mL), and stirred at 50° C. for 16 hours. Water was added to it, the formed solid was taken out through filtration, and the resulting solid was purified through silica gel column chromatography (chloroform/methanol), and crystallized from chloroform/diethyl ether to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.75 (1.0H, t, J=5.6 Hz), 8.35-8.28 (1.0H, m), 8.09 (1.0H, dd, J=8.8, 2.2 Hz), 8.04 (1.0H, s), 7.92 (1.0H, s), 7.35 (1.0H, s), 7.17 (1.0H, d, J=8.8 Hz), 7.00 (1.0H, s), 6.68 (2.0H, s), 4.31-4.02 (1.0H, m), 4.08 (4.0H, q, J=7.0 Hz), 3.86 (3.0H, s), 3.77 (2.0H, d, J=5.9 Hz), 3.64-3.02 (3.0H, m), 2.93 (2.0H, s), 2.10-1.72 (4.0H, m), 1.37 (6.0H, t, J=7.0 Hz). MS [M+H]+=590.

Provenance & Evidence