Isopropyl isocyanate → HCID 59375140, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-amino-4-(2-methyl-3-(1-methyl-1H-imidazole-2-carboxamido)phenyl)-9H-carbazole-1-carboxamide (Example 54-15, 29 mg, 0.066 mmol) and 2-isocyanatopropane (0.019 mL, 0.198 mmol) in 1,2-dichloroethane (3 mL) was stirred at rt for 2.5 h, then at 50° C. for 2 h. Additional 2-isocyanatopropane was added and the mixture was stirred at 40° C. for 16 h. The mixture was concentrated and purified by HPLC. The appropriate effluent fractions were partially concentrated, treated with NaHCO3 (aq) and extracted with EtOAc. The organic phase was dried and concentrated to provide 7-(3-isopropylureido)-4-(2-methyl-3-(1-methyl-1H-imidazole-2-carboxamido)phenyl)-9H-carbazole-1-carboxamide as a pale pink solid (15 mg, 43%). 1H NMR (400 MHz, DMSO-d6) δ 11.32 (1H, s), 9.97 (1H, s), 8.37 (1H, s), 8.13 (1H, br. s.), 7.88 (1H, d, J=7.9 Hz), 7.81 (1H, d, J=1.8 Hz), 7.76 (1H, d, J=7.9 Hz), 7.40-7.48 (2H, m), 7.38 (1H, t, J=7.7 Hz), 7.13 (1H, d, J=7.5 Hz), 7.06 (1H, s), 6.82-6.92 (2H, m), 6.73 (1H, d, J=8.3 Hz), 5.98 (1H, d, J=7.5 Hz), 4.01 (3H, s), 3.68-3.81 (1H, m), 1.89-1.95 (3H, m), 1.07 (6H, d). Mass spectrum m/z 524.3 (M+H)+.

Provenance & Evidence