Dimethylamine → HCID 89783640, compound

Participants

Reaction Conditions

Reaction Steps

A solution of rac-2-(3-fluoro-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 156; 32.0 mg, 0.103 mmol) and dimethylamine (2.0M in THF; 0.155 mL, 0.309 mmol) in DMSO (0.8 mL) was stirred under argon in a sealed microwave flask at 25° C. for 10 min, then at 60° C. for 18 h. Additional dimethylamine (2.0M in THF; 0.155 mL, 0.309 mmol) was added, and the resulting mixture was stirred under argon in a sealed microwave flask at 60° C. for 4.5 h. The reaction was cooled to 25° C. and diluted with water (10 mL). The precipitated solid was collected by vacuum filtration, washed with water (2×5 mL), and dried in vacuo to provide rac-2-(3-(dimethylamino)-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (22.7 mg, 0.068 mmol, 66% yield) as a yellow-orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.81 (1H, br. s.), 7.96 (1H, dd, J=7.5, 1.1 Hz), 7.66 (1H, dd, J=8.1, 0.9 Hz), 7.47 (1H, t, J=7.8 Hz), 7.08 (1H, d, J=2.2 Hz), 6.99 (1H, br. s.), 3.40-3.49 (1H, m), 3.13-3.15 (6H, m), 3.06-3.18 (2H, m), 2.71 (3H, s), 1.30 (3H, d, J=6.5 Hz). m/z (ESI, +ve) 336.2 (M+H)+.

Provenance & Evidence