Hydrochloric Acid → N-(2-aminophenyl)-4-{3-cyano-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzamide

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Reaction Steps

t-Butyl {2-[(4-{3-cyano-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzoyl)amino]phenyl}carbamate (586 mg, 1.06 mmol; prepared as described in Method 19) was dissolved in ethyl acetate (7 ml) and 3M aqueous hydrochloric acid (7 ml) was added. The resulting suspension was stirred for 6 hours at ambient temperature then 3M aqueous hydrochloric acid (1.75 ml) added. The suspension was stirred for a further 2 hours then 3M aqueous hydrochloric acid (3.5 ml) was added and stirred for 30 minutes. The suspension was poured into water (50 ml) and washed with ethyl acetate (3×15 ml). The resulting aqueous solution was basified using a 2M aqueous solution of sodium hydroxide. A pale yellow precipitate crashed out which was filtered and washed with water. The pale yellow solid was dried in a vacuum oven at 50° C. ovenight (294 mg, 62%); NMR Spectrum: (CDCl3) 0.99 (d, 6H), 2.48 (m, 8H), 2.60 (m, 1H) 3.56 (s, 2H), 3.79 (br s, 2H), 6.80 (m, 2H), 7.03 (m, 1H), 7.32 (d, 1H), 7.81 (br s, 1H), 7.99 (s, 4H), 8.04 (s, 1H), 8.74 (s, 1H); Mass Spectrum: M+H+ 455.

Provenance & Evidence