Tert-Butylamine → 2-(3-(tert-butylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

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Reaction Steps

A solution of 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (210i, 75 mg, 0.266 mmol) and 2-methylpropan-2-amine (56.1 μl, 0.531 mmol; Aldrich) in DMSO (2.6 ml) was stirred at 100° C. for 1 h. The mixture was diluted with DCM (150 ml), added to a separatory funnel, and washed with saturated aq. NaHCO3 (2×100 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. The impure material was dissolved in DMSO (˜20 mg/ml) and injected (4×1.0 ml) onto a Shimadzu preparatory LC (rpHPLC: Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% MeCN/water with 0.1% TFA) before the pure fractions were combined, basicified with NaHCO3 (saturated, aq.), extracted with DCM, separated, dried over Na2SO4, and concentrated via rotary evaporation to give 2-(3-(tert-butylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (210, 25% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (s, 9H) 2.87 (t, J=6.85 Hz, 2H) 3.45 (td, J=6.85, 2.35 Hz, 2H) 6.95 (br. s., 1H) 7.07 (d, J=2.15 Hz, 1H) 7.34 (t, J=7.82 Hz, 1H) 7.58 (s, 1H) 7.61 (dd, J=7.92, 1.27 Hz, 1H) 7.90 (dd, J=7.53, 1.27 Hz, 1H) 8.38 (s, 1H) 12.13 (br. s., 1H). MS (ESI, pos. ion) m/z: 336.2 (M+1).

Provenance & Evidence