Thiomorpholine 1,1-dioxide → HCID 66604564, compound

Participants

Reaction Steps

8-Carbamoyl-6-(3-fluoro-4-methoxyphenyl)-9H-carbazole-2-carboxylic acid (Example 395, 35 mg, 0.083 mmol), HATU (150 mg, 0.394 mmol), DMAP (50 mg, 0.409 mmol), Thiomorpholine-1,1-dioxide (90 mg, 0.666 mmol) and DMF (2 ml) were combined and stirred at room temperature for 3 days. The reaction mixture was filtered through a 0.45 um Nylon filter and purify by preparative HPLC. Product containing fractions were evaporated to give 26.3 mg 3-(3-fluoro-4-methoxyphenyl)-7-(1,1-dioxo-thiomorpholine-4-carbonyl)-9H-carbazole-1-carboxamide. MS (ESI) m/e+=496, m/e−=494, consistent with [M+H]+and [M−H]− resp. HPLC retention time 9.61 min. (Sunfire C18 3.5 μm, 4.6×150 mm column, 15 min gradient, 10-100% B, 1 mL/min. Solvent A: 5% CH3CN—95% H2O—0.1% TFA; Solvent B: 95% CH3CN—5% H2O—0.1% TFA). 1H NMR (DMSO-d6) δ ppm 11.60 (s, 1H), 8.73 (d, 1H, J=1.6), 8.39 (b, 1H), 8.34-8.30 (m, 2H), 7.86 (d, 1H, J=0.7), 7.81 (dd, 1H, J=13.3, 2.3), 7.71 (dd, 1H, J=8.5, 1.2), 7.60 (b, 1H), 7.35 (dd, 1H, J=8.1, 1.4), 7.31 (t, 1H, J=9.0), 3.92 (s, 3H), 4.2-3.7 (b, 4H), 3.35-3.25 (b, 4H).

Provenance & Evidence