Methanol → HCID 71730637, compound

Participants

Reaction Steps

Trimethyloxonium tetrafluoroborate (239 mg, 1.617 mmol, Sigma-Aldrich) was added to a red slurry of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193, 113 mg, 0.32 mmol) in DCM (10 mL) and the resulting mixture was stirred at RT for 1 h when the solid had begun to stick to the side of the flask; MeOH (2 mL) was added to bring all the solid into solution and stir at RT for 16 h when a mixture of product and starting material was observed via lcms. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel) with 100% DCM to 4% 2 M NH3 in MeOH/DCM to give N-(tert-butyl)-8-(4-methoxy-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-3-methylquinoxalin-2-amine (351, 16 mg, 14% yield) as a rust colored solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.66 (s, 9H) 2.55 (s, 3H) 2.82 (t, J=7.73 Hz, 2H) 3.84 (t, J=7.73 Hz, 2H) 3.88 (s, 3H) 4.84 (s, 1H) 6.80 (d, J=1.96 Hz, 1H) 7.36 (t, J=7.82 Hz, 1H) 7.63 (dd, J=8.12, 1.27 Hz, 1H) 7.91 (dd, J=7.63, 1.37 Hz, 1H) 12.54 (br. s., 1H). 13C NMR (101 MHz, CDCl3) δ ppm 21.30, 21.51, 28.68, 46.23, 51.32, 52.37, 100.94, 110.83, 124.51, 124.72, 125.43, 126.11, 131.26, 135.55, 136.41, 136.91, 145.19, 148.40, 161.58. MS (ESI, pos. ion) m/z: 364.4 (M+1).

Provenance & Evidence