6-Fluoro-2-methyl-3-nitropyridine → 1-((1R,2R)-2-((S)-1-(6-Methyl-5-nitropyridin-2-yl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea

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Reaction Steps

1-((1R,2R)-2-((S)-1-(6-Methyl-5-nitropyridin-2-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 6-fluoro-2-methyl-3-nitropyridine (54.3 mg, 0.35 mmol) according to General Procedure A to give 20 mg (14%) of yellow solid. Anal. Calcd. for C24H32N6O3 m/z 452.2, found: 453.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.82 (d, J=9.4 Hz, 1H), 7.17 (m, 4H), 6.98 (m, 1H), 6.59 (d, J=9.4 Hz, 1H), 6.02 (d, J=4.6 Hz, 1H), 4.74 (m, 1H), 4.16 (m, 1H), 3.68 (m, 1H), 3.54 (m, 2H), 3.26 (m, 2H), 2.57 (s, 3H), 2.39 (m, 1H), 2.12 (m, 3H), 1.92 (m, 4H), 1.47 (m, 4H).

Provenance & Evidence