2-Fluoro-5-(trifluoromethyl)pyridine → 1-Phenyl-3-((1R,2R)-2-((S)-1-(5-(trifluoromethyl)pyridin-2-yl)piperidin-3-ylamino)cyclohexyl)urea

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Reaction Steps

1-Phenyl-3-((1R,2R)-2-((S)-1-(5-(trifluoromethyl)pyridin-2-yl)piperidin-3-ylamino)cyclohexyl)urea 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-fluoro-5-(trifluoromethyl)pyridine (57.4 mg, 0.35 mmol) according to General Procedure A to give 15 mg (10.3%) of white solid. Anal. Calcd. for C24H30F3N5O m/z 461.2, found: 462.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 8.18 (m, 1H), 7.30 (m, 1H), 7.21 (m, 4H), 7.00 (m, 1H), 6.67 (d, J=8.9 Hz, 1H), 6.18 (d, J=5.4 Hz, 1H), 4.47 (m, 1H), 3.79 (m, 1H), 3.59 (m, 3H), 3.23 (m, 1H), 2.33 (m, 1H), 2.07 (m, 4H), 1.87 (m, 3H), 1.67 (d, J=7 Hz, 2H), 1.49 (m, 4H).

Provenance & Evidence