Trifluoroacetic acid → HCID 89783666, compound

Participants

Reaction Steps

To a slurry of NaH (60% in mineral oil; 0.064 g, 1.606 mmol) in 1 mL DMF at 0° C. was added methanesulfonamide (TCI America, Portland, Oreg.; 0.153 g, 1.606 mmol) in portions. The ice/water bath was removed and the reaction warmed to RT. 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 0.068 g, 0.229 mmol) was added. After 30 min, the reaction was cooled to 0° C., TFA (0.177 ml, 2.295 mmol) was added (dropwise via syringe), and 1 mL DMSO was added. The solution was filtered through a 0.45 micron syringe filter and purified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 10-70% ACN/H2O with 0.1% TFA); product-containing fractions were concentrated in vacuo, to give N-(3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)methanesulfonamide 2,2,2-trifluoroacetate (0.020 g, 0.041 mmol, 18% yield) as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (1H, br. s.), 10.98 (1H, br. s), 8.11 (1H, d, J=7.6 Hz), 7.74 (1H, dt, J=8.0, 0.8 Hz), 7.54-7.66 (1H, m), 7.05-7.15 (1H, m), 7.01 (1H, br. s.), 3.44 (2H, t, J=7.0 Hz), 3.39 (3H, s), 2.91 (2H, t, J=6.9 Hz), 2.68 (3H, s). m/z (ESI, +ve) 372.0 (M+H)+.

Provenance & Evidence