1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(1-Methylethyl)-1'-{[5-(tetrazol-5-yl)biphenyl-3-yl]carbonyl}spiro[7-azachroman-2,4'-piperidin]-4-one

Participants

Reaction Conditions

Reaction Steps

6-(1-Methylethyl)spiro[7-azachroman-2,4′-piperidin]-4-one hydrochloride (94 mg), 1-hydroxybenzotriazole monohydrate (36 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (57 mg), triethylamine (73 μL) and water (1 mL) were added in that order to a DMF (3 mL) solution of 5-(tetrazol-5-yl)biphenyl-3-carboxylic acid (50 mg), and stirred at 90° C. for 1 hour and 30 minutes. Water was added to the reaction liquid, the formed precipitate was taken out through filtration, washed with hexane/ethyl acetate=2/1, and dried to obtain the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.50 (1.0H, s), 8.38 (1.0H, s), 8.04 (1.0H, s), 7.87 (1.0H, s), 7.79 (2.0H, d, J=7.6 Hz), 7.54 (2H, t, J=7.6 Hz), 7.45 (1.011, t, J=7.6 Hz), 7.40 (1.0H, s), 4.40-4.22 (1.0H, m), 3.65-3.20 (3.0H, m), 3.01 (1.0H, q, J=6.8 Hz), 2.97 (2.0H, s), 2.15-2.05 (1.0H, m), 1.95-1.78 (3.0H, m), 1.18 (6.0H, d, J=6.8 Hz). MS [M+H]+=509.

Provenance & Evidence