1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

Participants

Reaction Conditions

Reaction Steps

6-(5-Oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (202 mg), 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (145 mg), EDCI (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 recrystallized from methanol to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.08-8.04 (2.0H, m), 8.00 (1.0H, dd, J=8.8, 2.2 Hz), 7.93-7.91 (1.0H, m), 7.25 (1.0H, d, J=8.5 Hz), 7.22 (2.0H, br s), 6.68 (2.0H, s), 4.37-4.13 (1.0H, m), 4.08 (4.0H, q, J=6.8 Hz), 3.86 (3.0H, s), 3.66-3.13 (3.0H, m), 2.95 (2.0H, s), 2.14-1.69 (4.0H, m), 1.37 (6.0H, t, J=7.0 Hz). MS [M+H]+=573.

Provenance & Evidence