N-bromobutanimide → HCID 178482048, compound

Participants

Reaction Steps

To a room temperature slurry of 4-(5-amino-6-(1-hydroxyisoquinolin-6-yl)pyrazin-2-yl)-N-cyclopropyl-N-methylbenzenesulfonamide hydrochloride (1.00 g, 2.07 mmoL, prepared by general method C) in DMF (10 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (1 mL). Within minutes, the slurry discharged to a solution. Then, N-bromosuccinimide (386 mg, 2.17 mmol) was added in one portion. After 1 h the reaction was concentrated and flashed over silica gel (4-8% MeOH/DCM eluent) to provide 4-(5-amino-6-(4-bromo-1-hydroxyisoquinolin-6-yl)pyrazin-2-yl)-N-cyclopropyl-N-methylbenzenesulfonamide hydrochloride (480 mg, 43% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.59-11.67 (br. s, 1H), 8.77 (s, 1H), 8.36 (d, J=8.3 Hz, 1H), 8.24-8.30 (m, 2H), 8.17 (d, J=1.5 Hz, 1H), 7.99 (dd, J=8.3, 1.5 Hz, 1H), 7.86 (d, J=8.5 Hz, 2H), 7.62 (d, J=6.0 Hz, 1H), 6.76 (br. s, 2H), 2.69 (s, 3H), 1.80-1.90 (m, 1H), 0.76 (s, 2H), 0.65-0.73 (m, 2H); MS (EI) m/z=527.4 [M+1]+.

Provenance & Evidence