Trifluoroacetic acid → HCID 71730505, compound

Participants

Reaction Steps

A solution of tert-butyl (2-methyl-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)propyl)carbamate (339) (0.13 g, 0.28 mmol) in DCM (2.80 mL) and TFA (1.0 mL, 13.99 mmol) was stirred at 0° C. for 20 min before it was warmed to RT and stir for 1 h. The reaction mixture was concentrated and the residue was diluted with CHCl3/IPA(3:2) (150 mL), added to a separatory funnel, and washed with saturated aq. NaHCO3 (2×75 mL) before the organic layer was separated, dried over Na2SO4, and concentrated to give 2-(3-((1-amino-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (65 mg, 0.17 mmol, 63% yield) which was impure by NMR. This material was dissolved in MeOH (˜20 mg/mL) and injected (2×1.0 mL) onto the Shimadzu preparatory LC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% MeCN/water with 0.1% TFA); the pure fractions were combined, basicified with NaHCO3 (saturated, aq.), extracted with CHCl3/IPA(3:2), separated, dried over Na2SO4, and concentrated via rotary evaporation to give 2-(3-((1-amino-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (341) (19 mg, 0.05 mmol, 18% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.60 (s, 6H) 2.59 (s, 3H) 2.95 (s, 2H) 2.99 (t, J=6.85 Hz, 2H) 3.65 (td, J=6.85, 2.54 Hz, 2H) 5.33 (br. s., 1H) 6.19 (s, 1H) 7.10 (d, J=2.15 Hz, 1H) 7.36 (t, J=7.82 Hz, 1H) 7.65 (dd, J=8.02, 1.37 Hz, 1H) 7.92 (dd, J=7.63, 1.37 Hz, 1H) 12.64 (br. s., 1H). MS (ESI, pos. ion) m/z: 365.3 (M+1).

Provenance & Evidence