1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 24857133, compound

Participants

Reaction Steps

TEA (162 mg) was added to a mixture of EDCI (92 mg), HOBT (73.5 mg), 1-cyclopropyl-4-ethoxy-3-methyl-1H-indole-6-carboxylic acid (104 mg), and methyl 5-(4-oxospiro[chroman-2,4′-piperidin]-6-yl)nicotinate dihydrochloride (170 mg) and DMF (3 ml), and the mixture was stirred at r.t. for 5 hours. The mixture was evaporated and purified through SiO2 column chromatography (eluted with Hex-EtOAc, then MeOH—CHCl3) to give methyl ester of the title compound as a pale yellow solid. 1 ml of 1N NaOHaq was added to its solution in 3 ml of MeOH and 3 ml of THF, and the mixture was stirred at r.t. for 4 h. Then the mixture was neutralized with 1N HClaq and diluted with CHCl3-MeOH. The mixture was dried over Na2SO4, filtered, and concentrated. The residue was crystallized from EtOAc-n-hexane to give the title compound as a slightly yellowish powder. 1H-NMR (400 MHz, DMSO-d6) δ: 13.57 (1H, s), 9.08 (1H, d, J=2.0 Hz), 9.03 (1H, d, J=2.0 Hz), 8.41 (1H, dd, J=2.0, 2.0 Hz), 8.08-8.02 (2H, m), 7.26 (1H, dd, J=7.8, 1.0 Hz), 7.12 (1H, d, J=1.0 Hz), 7.00 (1H, d, J=1.0 Hz), 6.48 (1H, s), 4.36-4.14 (1H, br m), 4.08 (2H, q, J=7.0 Hz), 3.78-3.20 (4H, br m), 2.96 (2H, s), 2.33 (3H, d, J=1.0 Hz), 2.09-1.73 (4H, m), 1.37 (3H, t, J=7.0 Hz), 1.03-0.98 (2H, m), 0.89-0.85 (2H, m); MS [M+H]+=580.

Provenance & Evidence