m-Tolyl isocyanate → HCID 71226857, compound

Participants

Reaction Steps

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-m-tolylurea 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 1-isocyanato-3-methylbenzene (22.3 mg, 0.17 mmol) according to General Procedure G to give 20 mg (27.7%) of a white solid. Anal. Calcd. for C26H33N5O m/z 431.3, found: 432.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (s, 1H), 7.39 (d, J=8.9 Hz, 2H), 7.20 (s, 2H), 7.10 (t, J=8.1 Hz, 1H), 6.92 (d, J=8.9 Hz, 2H), 6.71 (d, J=7.4 Hz, 1H), 6.15 (d, J=7.6 Hz, 1H), 3.89 (d, J=11.1 Hz, 1H), 3.77 (d, J=13.2 Hz, 1H), 3.26 (d, J=8.9 Hz, 1H), 2.79 (m, 1H), 2.57 (m, 1H), 2.42 (m, 1H), 2.24 (s, 1H), 1.88 (m, 3H), 1.65 (m, 4H), 1.45 (m, 1H), 1.21 (m, 4H), 1.11 (m, 1H).

Provenance & Evidence