Methyl iodide → HCID 70654872, compound

Participants

Reaction Steps

To a room temperature slurry of 4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)-N-((1R,2R)-2-methylcyclopropyl)benzenesulfonamide hydrochloride (110 mg, 0.227 mmol) and cesium carbonate (222 mg, 0.681 mmol) was added methyl iodide (16.0 μL, 0.251 mmol). At completion, the reaction was filtered and concentrated, then flashed over silica gel (5-10% MeOH/DCM eluent) to provide 4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)-N-methyl-N-((1R,2R)-2-methylcyclopropyl)-benzenesulfonamide (90 mg, 86% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.55 (s, 1H), 8.25 (d, J=7.8 Hz, 1H), 8.16 (d, J=8.5 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 7.83 (dd, J=8.0, 1.5 Hz, 1H), 7.70 (s, 1H), 5.95 (br. s, 1H), 5.14 (br. s, 2H), 3.66 (dt, J=7.0, 2.3 Hz, 2H), 3.14 (t, J=7.0 Hz, 2H), 2.76 (s, 3H), 1.48-1.53 (m, 1H), 1.27-1.35 (m, 1H), 1.06 (d, J=6.3 Hz, 3H), 0.96-1.02 (m, 1H), 0.47 (dd, J=12.3, 6.0 Hz, 1H); MS (EI) m/z=464.5 [M+1]+.

Provenance & Evidence