Picolinoyl Chloride Hydrochloride → HCID 59375137, compound

Participants

Reaction Steps

A solution of benzyl 5-(3-amino-2-methylphenyl)-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate, TFA salt (Example 51-1, 55 mg, 0.094 mmol), TEA (0.066 mL, 0.472 mmol), and picolinoyl chloride hydrochloric acid salt (50.4 mg, 0.283 mmol) in DCM (8 mL) was stirred at rt overnight. The mixture was concentrated and purified by preparative HPLC to provide benzyl 8-carbamoyl-5-(2-methyl-3-(picolinamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate, isolated as the TFA salt, as a white solid (26 mg, 39%). 1H NMR (400 MHz, methanol-d4) δ 8.59 (1 H, t, J=4.8 Hz), 8.14 (1 H, d, J=8.3 Hz), 7.89-7.99 (1 H, m), 7.85 (1 H, dd, J=9.9, 8.1 Hz), 7.50 (2 H, dd, J=7.7, 2.0 Hz), 7.11-7.32 (6 H, m), 7.01 (1 H, d, J=7.9 Hz), 6.74 (1 H, d, J=7.5 Hz), 4.96 (2 H, s), 3.68-3.87 (1 H, m), 2.96-3.10 (1 H, m), 2.49-2.66 (1 H, m), 1.82-2.11 (5 H, m), 1.73 (1 H, br. s.), 1.34-1.62 (1 H, m). Mass spectrum m/z 575.1 (M+H)+.

Provenance & Evidence