Trifluoroacetic acid → HCID 59374985, compound

Participants

Reaction Steps

A solution of racemic 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 44-4, 30 mg, 0.052 mmol) in methanol-DMSO was treated with TFA (0.5 mL) and the solution was stirred overnight at rt. The mixture was concentrated and purified by preparative HPLC to provide 7-(2,3-dihydroxypropoxy)-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a white solid (9.4 mg, 32%). 1H NMR (400 MHz, DMSO-d6) δ 11.39 (1 H, s), 8.16 (1 H, br. s.), 7.94 (1 H, d, J=7.7 Hz), 7.54-7.65 (3 H, m), 7.49 (3 H, t, J=7.9 Hz), 7.25-7.38 (2 H, m), 6.99 (1 H, d, J=7.7 Hz), 6.92 (1 H, d, J=8.8 Hz), 6.60 (1 H, d, J=1.3 Hz), 4.82-5.01 (3 H, m), 4.60-4.71 (1 H, m), 3.96-4.08 (1 H, m), 3.76-3.96 (2 H, m), 3.48 (2H, t, J=5.6 Hz), 2.44 (3 H, s), 1.77-1.88 (3 H, m). Mass spectrum m/z 536.1 (M+H)+.

Provenance & Evidence