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

Participants

Reaction Steps

4-(Trifluoromethoxy)benzyl (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-(trifluoromethoxy)benzyl carbonochloridate (65.8 mg, 0.18 mmol) according to General Procedure H to give 30 mg (34.7%) of light brown solid. Anal. Calcd. for C27H31F3N4O3 m/z 516.2, found: 517.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.54 (d, J=8.8 Hz, 2H), 7.46 (d, J=8.4 Hz, 2H), 7.32 (d, J=8.0 Hz, 1H), 7.17 (d, J=8.04 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 5.05 (t, J=8.1 Hz, 2H), 3.89 (m, 1H), 3.8 (m, 1H), 3.10 (m, 1H), 2.77 (m, 1H), 2.39 (m, 2H), 1.92 (m, 1H), 1.81 (m, 2H), 1.66 (m, 3H), 1.47 (m, 1H), 1.18 (m, 7H), 1.04 (m, 1H).

Provenance & Evidence