Acetic Anhydride → HCID 59375109, compound

Participants

Reaction Steps

A solution of crude 7-(aminomethyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 33-1, 60 mg, 0.065 mmol) and TEA (23 μL, 0.163 mmol) in THF (1.3 mL) was treated with acetic anhydride (7.4 μL, 0.078 mmol) and the mixture was stirred at rt overnight. The mixture was concentrated and the residue was purified by preparative HPLC. The appropriate effluent fractions were concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated to provide 7-(acetamidomethyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as an off-white solid (12 mg, 36%). 1H NMR (400 MHz, DMSO-d6) δ 11.51 (1H, s), 8.29-8.45 (1H, m), 8.18 (1H, br. s.), 8.01 (1H, d, J=7.9 Hz), 7.81 (1H, d, J=7.5 Hz), 7.69 (2H, d, J=4.0 Hz), 7.60-7.65 (2H, m), 7.57 (1H, ddd, J=7.9, 4.2, 4.0 Hz), 7.50 (2H, t, J=7.8 Hz), 7.34 (1H, dd, J=7.7, 1.1 Hz), 6.94-7.06 (2H, m), 6.87 (1H, dd, J=8.3, 1.4 Hz), 4.90-5.04 (2H, m), 4.35 (2H, t, J=5.2 Hz), 1.89 (3H, s), 1.84 (3H, s). Mass spectrum m/z 503.2 (M+H)+.

Provenance & Evidence