Chlorosuccinimide → HCID 89781889, compound

Participants

Reaction Steps

To a 25-mL round-bottomed flask was added 2-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (357) (68 mg, 0.20 mmol), N-chlorosuccinimide (33 mg, 0.24 mmol) (Alfa-Aesar, Ward Hill, Mass.), and CHCl3 (3 mL). The reaction mixture was stirred at RT for 16 h and partitioned between water (5 mL) and EtOAc (5 mL). The organic extract was washed with brine (5 mL), dried over Na2SO4, and concentrated. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0-3% MeOH in DCM to provide 3-chloro-2-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (358) (9 mg, 12% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 13.75 (s, 1H), 8.40 (dd, J=1.27, 7.73 Hz, 1H), 7.75 (s, 2H), 7.70 (dd, J=1.27, 8.12 Hz, 1H), 7.44 (t, J=7.82 Hz, 1H), 4.32 (s, 2H), 2.51 (s, 3H), 1.45 (s, 3H), 0.90-0.95 (m, 2H), 0.73-0.79 (m, 2H). m/z (ESI, +ve) 368.1 (M+H)+.

Provenance & Evidence