1,2-Dichloroethane → HCID 59375073, compound

Participants

Reaction Steps

A mixture of benzyl 5-(3-amino-2-methylphenyl)-8-carbamoyl-9H-carbazol-2-ylcarbamate (Example 51-2, 100 mg, 0.215 mmol), 5-fluoropicolinic acid (45.6 mg, 0.323 mmol), HOAT (44.0 mg, 0.323 mmol), and EDC (83 mg, 0.431 mmol) in DCM-THF (80:20, 12 mL) was treated with DIEA (0.150 mL, 0.861 mmol) and the solution was stirred at rt overnight. The mixture was concentrated and purified by preparative HPLC to provide benzyl 8-carbamoyl-5-(3-(5-fluoropicolinamido)-2-methylphenyl)-9H-carbazol-2-ylcarbamate as a white solid (47 mg, 36%). 1H NMR (400 MHz, DMSO-d6) δ 11.48 (1 H, s), 10.41 (1 H, s), 9.83 (1 H, s), 8.74 (1 H, d, J=3.0 Hz), 8.27 (1 H, dd, J=8.8, 4.8 Hz), 8.09-8.21 (1 H, m), 7.96-8.03 (2 H, m), 7.94 (1 H, d, J=7.8 Hz), 7.85 (1 H, d, J=7.5 Hz), 7.29-7.51 (7 H, m), 7.15-7.21 (1 H, m), 6.91-6.98 (2 H, m), 6.79 (1 H, d, J=8.8 Hz), 5.16 (2 H, s), 1.96 (3 H, s). Mass spectrum m/z 588.1 (M+H)+.

Provenance & Evidence