N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide → 4-Ethoxybenzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate

Participants

Reaction Steps

4-Ethoxybenzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (50 mg, 0.17 mmol) and 4-ethoxybenzyl carbonochloridate (58.5 mg, 0.18 mmol) according to General Procedure H to give 65 mg (81%) of pale yellow solid. Anal. Calcd. for C28H36N4O3 m/z 476.3, found: 477.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52 (d, J=8.9 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 1H), 7.04 (d, J=8.6 Hz, 1H), 6.95 (d, J=9 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 4.92 (m, 2H), 3.98 (m, 2H), 3.86 (d, J=6.9 Hz, 1H), 3.75 (d, J=12.5 Hz, 1H), 3.07 (m, 1H), 2.76 (m, 1H), 2.35 (m, 2H), 1.89 (m, 1H), 1.78 (m, 2H), 1.64 (m, 3H), 1.44 (m, 1H), 1.30 (t. J=7 Hz, 3H), 1.17 (m, 4H), 1.02 (m, 1H).

Provenance & Evidence