Acetic Anhydride → HCID 89783436, compound

Participants

Reaction Conditions

Reaction Steps

Ac2O (4.49 μl, 0.048 mmol) was added to a mixture of 2-(3-(azetidin-3-ylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (20.0 mg, 0.043 mmol) and DIPEA (0.023 mL, 0.130 mmol) in DCM (1.0 mL), and the resulting yellow suspension was stirred at 25° C. for 10 min. The mixture was concentrated in vacuo, and the residue was taken up in in DMSO (2.0 mL) and purified by reversed-phase HPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA) to provide 2-(3-((1-acetylazetidin-3-yl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (19.0 mg, 0.038 mmol, 87% yield) as a red solid: 1H NMR (400 MHz, MeOH-d4) δ ppm 7.86 (1H, d, J=7.4 Hz), 7.66 (1H, d, J=7.4 Hz), 7.44 (1H, t, J=7.8 Hz), 7.18 (1H, s), 4.89-4.97 (1H, m), 4.69 (1H, t, J=8.3 Hz), 4.46 (1H, dd, J=9.9, 8.1 Hz), 4.23 (1H, dd, J=9.2, 5.1 Hz), 4.05 (1H, dd, J=10.4, 5.1 Hz), 3.64 (2H, t, J=7.1 Hz), 3.04 (2H, t, J=7.0 Hz), 2.66 (3H, s), 1.91 (3H, s). 19F NMR (376 MHz, MeOH-d4) δ ppm −77.73 (3F, s). m/z (ESI, +ve) 391.1 (M+H)+.

Provenance & Evidence