1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1'-[(1-Cyclopropyl-4-methoxy-1H-indol-6-yl)carbonyl]-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

Participants

Reaction Steps

Et3N (58 μL), HOBT (32 mg) and WSC (40 mg) were added to a solution of 1-cyclopropyl-4-methoxy-1H-indol-6-carboxylic acid (40 mg) and 6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (70 mg) in DMF (4 mL), and stirred overnight at room temperature. Water was added to the reaction mixture, and the formed solid was collected by filtration. The solid was washed thoroughly with water and ether. This was dried under reduced pressure to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 12.91 (1H, brs), 8.20 (1H, d, J=4.0 Hz), 8.00 (1H, dd, J=8.0, 4.0 Hz), 7.36-7.26 (2H, m), 7.22 (1H, s), 6.57 (1H, s), 6.39 (1H, d, J=4.0 Hz), 4.20-4.00 (1H, m), 3.87 (3H, s), 3.46-3.40 (1H, m), 3.40-3.20 (3H, m), 2.89 (2H, s), 2.06-1.77 (4H, m), 1.07-1.03 (2H, m), 0.94-0.90 (2H, m); MS [M+H]+=515.

Provenance & Evidence