Hydrochloric Acid → 1'-{[1-Cyclopropyl-4-(tetrazol-5-yl)-1H-indol-6-yl]carbonyl}-6-[6-(methyloxy)pyridin-3-yl]spiro[chroman-2,4'-piperidin]-4-one

Participants

Reaction Conditions

Reaction Steps

6-[6-(Methyloxy)pyridin-3-yl]spiro[chroman-2,4′-piperidin]-4-one dihydrochloride (238 mg), 1-cyclopropyl-4-(tetrazol-5-yl)-1H-indole-6-carboxylic acid (135 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. 1N hydrochloric acid and water were added to the reaction liquid, 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: 8.43 (1.0H, d, J=2.7 Hz), 7.98 (1.0H, dd, J=8.7, 2.7 Hz), 7.93-7.88 (2.0H, m), 7.87-7.83 (2.0H, m), 7.65 (1.0H, d, J=3.2 Hz), 7.21 (1.0H, d, J=8.3 Hz), 7.12 (1.0H, d, J=3.2 Hz), 6.88 (1.0H, d, J=8.3 Hz), 4.50-3.97 (1.0H, m), 3.88 (3.0H, s), 3.80-3.17 (4.0H, m), 2.94 (2.0H, s), 2.17-1.91 (2.0H, br m), 1.89-1.77 (2.0H, m), 1.16-1.09 (2.0H, m), 1.04-0.99 (2.0H, m). MS [M+H]+=576.

Provenance & Evidence