Trifluoroacetic acid → N-(2-Aminophenyl)-4-{1-[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzamide

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Reaction Steps

tert-Butyl {2-[(4-{1-[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzoyl)amino]phenyl}carbamate (prepared as described in Method 7; 308 mg, 0.61 mmol) was taken up in dichloromethane (2 ml) and trifluoroacetic acid (1 ml) added. The reaction mixture was stirred at ambient temperature for 1 hour before being poured onto an SCX-3 cartridge (5 g). The cartridge was washed with dichloromethane (50 ml) and methanol (50 ml), before eluting the product with a 2M solution of ammonia in methanol (50 ml). The ammoniacal fraction was evaporated to afford a white solid (182 mg) that was purified by reverse phase preparative HPLC to afford the title compound (134 mg, 55%); NMR Spectrum: (DMSO d6) δ 1.70 (m, 4H), 2.01 (m, 2H), 2.22 (s, 3H), 2.57 (m, 1H), 2.95 (m, 2H), 3.28 (s, 2H), 3.71 (s, 3H), 4.86 (s, 2H), 6.60 (m, 1H), 6.78 (m, 1H), 6.97 (m, 1H), 7.17 (m, 1H), 7.23 (s, 1H), 7.37 (d, 2H), 7.90 (d, 2H), 9.55 (s, 1H); Mass Spectrum: M+H+404.

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