4-Chloro-2-pyridinecarbonitrile → 1-((1R,2R)-2-((S)-1-(2-Cyanopyridin-4-yl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea

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Reaction Steps

1-((1R,2R)-2-((S)-1-(2-Cyanopyridin-4-yl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea was synthesized using 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea (from intermediate C, Example 1) (100 mg, 0.32 mmol) and 4-chloropicolinonitrile (44 mg, 0.15 mmol) according to General Procedure A to give 29.3 mg (22.1%) of pale brown oil. Anal. Calcd. for C24H30N6O m/z 418.2, found: 419.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.89 (d, J=6.5 Hz, 1H), 7.35 (d, J=2.7 Hz, 1H), 7.25 (m, 4H), 7.04 (m, 2H), 4.08 (m, 1H), 3.72 (m, 2H), 3.60 (m, 1H), 3.51 (m, 1H), 3.25 (m, 2H), 2.31 (m, 1H), 2.15-2.05 (m, 4H), 1.98-1.88 (m, 3H), 1.63-1.42 (m, 5H).

Provenance & Evidence