Diisopropylethylamine → HCID 71730510, compound

Participants

Reaction Steps

A solution of 2-(3-(tert-butylamino)-2-chloroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (345) (28 mg, 0.07 mmol), azetidin-3-ol hydrochloride (41 mg, 0.37 mmol, Matrix Scientific, Columbia, S.C.), and N-ethyl-N-isopropylpropan-2-amine (81 pt, 0.45 mmol) in DMSO (0.75 mL) was stirred at 50° C. for 1 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 1-5% of 2 M NH3 in MeOH/DCM to give 2-(3-(tert-butylamino)-2-(3-hydroxyazetidin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (346) (19 mg, 61% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (s, 9H) 2.85 (t, J=6.94 Hz, 2H) 3.43 (td, J=6.75, 2.35 Hz, 2H) 3.94 (dd, J=9.00, 5.09 Hz, 2H) 4.41 (dd, J=8.80, 6.85 Hz, 2H) 4.57 (sxt, J=5.91 Hz, 1H) 5.64-5.71 (m, 2H) 6.95 (s, 1H) 6.96 (s, 1H) 7.24 (t, J=7.82 Hz, 1H) 7.36 (dd, J=7.92, 1.27 Hz, 1H) 7.61 (dd, J=7.43, 1.37 Hz, 1H) 12.00 (s, 1H). MS (ESI, pos. ion) m/z: 407.1 (M+1).

Provenance & Evidence