Piperidine → t-Butyl[2-({4-[3-cyano-5-(piperidin-1-ylmethyl)pyridin-2-yl]benzoyl}amino)phenyl]carbamate

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Reaction Steps

A solution of N-(2-t-butoxycarbonylaminophenyl)-4-(3-cyano-5-formylpyridin-2-yl)benzamide (400 mg, 0.905 mmol, prepared as described in Method 15) in dichloromethane (5 ml) was added over 20 min to a stirred mixture of piperidine (0.1 ml, 1.00 mmol) sodium triacetoxyborohydride (212 mg, 1.0 mmol), powdered 3A molecular sieve (500 mg) and dichloromethane (15 ml) at −20° C. under nitrogen. The reaction mixture was stirred for 16 hours at ambient temperature before being filtered and washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica eluting with ethyl acetate to afford the title compound as a cream solid (252 mg, 55%); NMR Spectrum: (DMSO-d6) 1.40 (m, 2H), 1.45 (s, 9H), 1.46 (m, 4H), 2.39 (m 4H), 3.58 (s, 2H), 7.17 (m, 2H), 7.56 (m, 2H), 8.01 (d, 2H), 8.12 (d, 2H), 8.31 (d, 1H), 8.69 (s, 1H), 8.87 (d, 1H), 9.94 (s, 1H); Mass Spectrum: M+H+512.

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