Diisopropylethylamine → HCID 71730508, compound

Participants

Reaction Steps

A solution of 2-(3-(tert-butylamino)-2-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (343) (16 mg, 0.04 mmol), methanamine hydrochloride (15 mg, 0.22 mmol, Sigma-Aldrich), and DIEA (47.4 μL, 0.27 mmol) in DMSO (0.45 mL) was stirred at RT for 2 h. The reaction mixture was diluted with DCM (100 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. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel) with 1-4% of 2 M NH3 in MeOH/DCM to give 2-(3-(tert-butylamino)-2-(methylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4 (5H)-one (344) (4 mg, 24% yield) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (s, 9H) 2.85 (t, J=6.85 Hz, 2H) 2.95 (d, J=4.30 Hz, 3H) 3.42 (td, J=6.80, 2.45 Hz, 2H) 6.32 (s, 1H) 6.89 (d, J=2.15 Hz, 1H) 6.90 (br. s., 1H) 7.17 (t, J=7.63 Hz, 1H) 7.28 (dd, J=8.02, 1.37 Hz, 1H) 7.30-7.33 (m, 1H) 7.51 (dd, J=7.63, 1.37 Hz, 1H) 12.10 (br. s., 1H). MS (ESI, pos. ion) m/z: 365.3 (M+1).

Provenance & Evidence