Reaction Steps
A solution of 7-amino-4-(3-(4-fluorobenzamido)-2-methylphenyl)-9H-carbazole-1-carboxamide (Example 54-5, 30 mg, 0.066 mmol) and TEA (0.018 mL, 0.133 mmol) in DCM-THF (2:1, 3 mL) was treated with methanesulfonyl chloride (10 μL, 0.133 mmol). The mixture was stirred at rt for 1.5 h, and was concentrated and purified by preparative HPLC to provide 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(methylsulfonamido)-9H-carbazole-1-carboxamide as a white solid (Example 59-1, 3.5 mg, 9%). 1H NMR (500 MHz, methanol-d4) δ 7.91-8.01 (2H, m), 7.83 (1H, d, J=7.8 Hz), 7.45 (1H, d, J=1.7 Hz), 7.42 (1H, d, J=7.8 Hz), 7.34 (1H, t, J=7.8 Hz), 7.12-7.20 (3H, m), 6.95 (1H, d, J=7.8 Hz), 6.88 (1H, d, J=8.6 Hz), 6.73 (1H, dd, J=8.5, 2.1 Hz), 2.85 (3H, s), 1.90 (3H, s). Mass spectrum m/z 531.0 (M+H)+. Also obtained was 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(N-(methylsulfonyl)methylsulfonamido)-9H-carbazole-1-carboxamide as a white solid (Example 59-2, 14 mg, 28%). 1H NMR (400 MHz, DMSO-d6) δ 11.67 (1H, s), 10.08 (1H, s), 8.21 (1H, br. s.), 7.97-8.08 (3H, m), 7.79 (1H, d, J=1.8 Hz), 7.53 (1H, br. s.), 7.48 (1H, d, J=7.3 Hz), 7.26-7.39 (3H, m), 7.15 (1H, d, J=6.5 Hz), 6.93-7.03 (2H, m), 6.86 (1H, d, J=8.3 Hz), 3.46 (6H, d, J=9.0 Hz), 1.86 (3H, s). Mass spectrum m/z 607.2 (M−H)−.
