To a solution of 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylic acid (54 mg) and 5-[4-oxo-spiro(chroman-2,4′-piperidin)-6-yl]-4H-1,2,4-triazole-3-carboxamide (102 mg) in DMF (4 mL) were added TEA (77 uL), HOBT (42 mg), and WSC (53 mg) at room temperature and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into H2O, extracted with CHCl3, dried over sodium sulfate, filtered, and concentrated in reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of CHCl3/MeOH (1:0-10:1) as eluent to give the title compound as a colorless solid. 1H-NMR (400 MHz, CDCl3) δ: 8.78-8.60 (1H, m), 8.40-8.25 (1H, m), 7.29 (1H, s), 7.15 (1H, d, J=8.0 Hz), 7.09 (1H, d, J=4.0 Hz), 6.57 (1H, s), 6.52 (1H, d, J=4.0 Hz), 4.30-4.17 (1H, m), 3.95 (3H, s), 3.62-3.38 (3H, m), 3.38-3.32 (1H, m), 2.85 (2H, s), 2.28-1.70 (4H, m), 1.06-1.04 (2H, m), 1.00-0.97 (2H, m); MS [M+H]+=541.
