1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1'-[(1-cyclopropyl-4-methoxy-1H-indol-6-yl)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

Et3N (209 uL), HOBT (91.2 mg) and WSC (115 mg) were added to a suspension of 1-cyclopropyl-4-(methyloxy)-1H-indole-6-carboxylic acid (116 mg) and 6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (202 mg) in DMF (3 mL), and the mixture was stirred overnight at 50° C. Water was added to the reaction mixture, and the formed solid was collected by filtration. The solid was purified by silica gel column chromatography (CHCl3/MeOH) to obtain the intended compound as colorless foam. 1H-NMR (400 MHz, DMSO-d6) δ: 8.06 (1H, d, J=2.3 Hz), 8.00 (1H, dd, J=8.7, 2.3 Hz), 7.29 (1H, d, J=3.2 Hz), 7.26 (1H, d, J=8.7 Hz), 7.24-7.21 (3H, m), 6.58 (1H, d, J=1.0 Hz), 6.40 (1H, dd, J=3.2, 1.0 Hz), 4.44-4.08 (1H, br m), 3.87 (3H, s), 3.80-3.25 (4H, m), 2.97 (2H, s), 2.10-1.70 (4H, m), 1.09-1.01 (2H, m), 0.96-0.89 (2H, m); MS [M+H]+=514.

Provenance & Evidence