Ammonium formate → (R)-4-(3-aminopiperidin-1-yl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-benzyl 1-(1-carbamoyl-7-(4-methylpiperazine-1-carbonyl)-9H-carbazol-4-yl)piperidin-3-ylcarbamate (Example 16-1, 80 mg, 0.141 mmol), 10% palladium on carbon (14.97 mg, 0.014 mmol) and ammonium formate (53.2 mg, 0.844 mmol) in methanol (8 mL) was flushed with nitrogen and heated at 75° C. for 1 h. The mixture was cooled to rt, diluted with methanol and filtered through a Celite pad. The filtrate was concentrated to provide (R)-4-(3-aminopiperidin-1-yl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide as a white solid (75 mg, 98%). 1H NMR (400 MHz, methanol-d4) δ 8.13 (d, J=8.13 Hz, 1H) 7.86 (d, J=8.35 Hz, 1H) 7.68 (s, 1H) 7.29 (d, J=9.67 Hz, 1H) 6.86 (d, J=8.35 Hz, 1H) 3.54-3.72 (m, 2H) 3.24-3.53 (m, 5H) 2.88 (s, 3H) 2.11-2.29 (m, 1H) 1.92-2.11 (m, 2H) 1.44-1.73 (m, 1H). Mass spectrum m/z 435.2 (M+H)+.

Provenance & Evidence