Divinyl sulfone → HCID 66604190, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-amino-2-(4-(morpholinomethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (50 mg, 0.125 mmol), vinyl sulfone (0.13 mL, 1 3 mmol) in 2-propanol (3 mL) was stirred at 100° C. overnight. The solvent was removed and preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 7-(1,1-dioxido-4-thiomorpholinyl)-2-(4-(4-morpholinylmethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (6 mg, 10.97 μmol, 8.81% yield). MS (ESI) m/z 520.22 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.22 (1H, s), 8.54 (1H, br. s.), 8.30 (1H, s), 8.22 (2H, d, J=8.24 Hz), 8.09 (1H, d, J=8.55 Hz), 7.82 (1H,s),7.46 (2H, d, J=7.93 Hz), 7.32 (1H, d, J=2.14 Hz), 7.07 (1H, dd, J=8.85, 2.14 Hz), 3.88 (4H, br. s.), 3.58-3.65 (4H, m), 3.55 (2H, s), 3.20-3.27 (4H, m), 2.41 (4H, br. s.).

Provenance & Evidence