p-(Trifluoromethoxy)phenyl isocyanate → 1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-(trifluoromethoxy)phenyl)urea

Participants

Reaction Steps

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-(trifluoromethoxy)phenyl)urea was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (40 mg, 0.13 mmol) and 1-isocyanato-4-(trifluoromethoxy)benzene (27.2 mg, 0.13 mmol) according to General Procedure G to give 25 mg (37.2%) of white solid. Anal. Calcd. for C26H30F3N5O2 m/z 501.2, found: 502.0 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.7 (s, 1H), 7.49 (d, J=9 Hz, 2H), 7.40 (d, J=8.9 Hz, 2H), 7.23 (d, J=8.9 Hz, 2H), 6.92 (d, J=8.9 Hz, 2H), 6.13 (d, J=7.4 Hz, 1H), 3.87 (d, J=11.8 Hz, 1H), 3.76 (d, J=12.9 Hz, 1H), 3.28 (m, 1H), 2.79 (m, 1H), 2.60 (m, 2H), 2.44 (m, 2H), 1.91 (m, 1H), 1.65 (m, 3H), 1.48 (m, 1H), 1.24 (m, 6H), 1.11 (m, 1H).

Provenance & Evidence