Hydrochloric Acid → 5-{1'-[(1-Cyclopropyl-4-methoxy-1H-indol-6-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinic acid

Participants

Reaction Conditions

Reaction Steps

N,N′-carbonyldiimidazole (130 mg) and triethylamine (0.446 mL) were added to a solution of 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylic acid (185 mg) in DMF (4 mL), and stirred at 70° C. for 20 hours. To the reaction mixture was added 5-(4-oxo-spiro[chroman-2,4′-piperidin]-6-yl)nicotinic acid hydrochloride (370 mg), which was further stirred at that temperature for 6 hours. 1 N hydrochloric acid and water were added to the reaction mixture, and the formed solid was collected by filtration. The solid was purified through silica gel column chromatography (chloroform/methanol) to obtain the intended compound. 1H-NMR (400 MHz, DMSO-d6) δ: 9.04-9.00 (2H, m), 8.40 (1H, s), 8.06-8.00 (2H, m), 7.30-7.22 (3H, m), 6.58 (1H, s), 6.40 (1H, d, J=3.2 Hz), 4.47-4.01 (1H, m), 3.88 (3H, s), 3.79-3.09 (4H, m), 2.96 (2H, s), 2.15-1.71 (4H, m), 1.09-1.01 (2H, m), 0.96-0.89 (2H, m); MS [M+H]+=552.

Provenance & Evidence