2-Chloronicotinamide → 2-((S)-3-((1R,2R)-2-(3-Phenylureido)cyclohexylamino)piperidin-1-yl)nicotinamide

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Reaction Steps

2-((S)-3-((1R,2R)-2-(3-Phenylureido)cyclohexylamino)piperidin-1-yl)nicotinamide 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 2-chloronicotinamide (49 mg, 0.32 mmol) according to General Procedure A to give 9 mg (6.5%) of pale brown oil. Anal. Calcd. for C24H32N6O2 m/z 436.3, found: 437.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 8.2 (d, J=3.8 Hz, 1H), 7.65 (dd, J=2 Hz, 1H), 7.21 (m, 4H), 7.01 (m, 1H), 6.86 (m, 1H), 3.66 (m, 4H), 3.21 (m, 3H), 2.35 (m, 1H), 2.10 (m, 2H), 1.89 (m, 4H), 1.74 (m, 1H), 1.68 (d, J=1.68 Hz, 1H), 1.60 (m, 1H), 1.45 (m, 3H).

Provenance & Evidence