Isopropyl isocyanate → HCID 86663003, compound

Participants

Reaction Steps

A solution of 7-(aminomethyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 33-1, 30 mg, 0.065 mmol) and 2-isocyanatopropane (0.019 mL, 0.195 mmol) in THF (3 mL) was stirred at 40° C. overnight. The mixture was concentrated and purified by preparative HPLC. The appropriate effluent fractions were concentrated and partitioned between EtOAc and NaHCO3 (aq). The organic phase was dried and concentrated to provide 7-(3-isopropylureido)methyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a white solid (5.8 mg, 14%). 1H NMR (400 MHz, methanol-d4) δ 7.84 (1 H, d, J=7.7 Hz), 7.77 (1 H, d, J=7.5 Hz), 7.53-7.63 (2 H, m), 7.38-7.51 (4 H, m), 7.30 (1 H, dd, J=7.2, 1.7 Hz), 6.93-6.99 (2 H, m), 6.85 (1 H, dd, J=8.3, 1.4 Hz), 4.79-4.91 (2 H, m), 4.33 (2 H, s), 3.69-3.78 (1 H, m), 1.79 (3 H, s), 1.03 (6 H, d, J=6.4 Hz). Mass spectrum m/z 546.3 (M+H)+.

Provenance & Evidence