Acetic Anhydride → 1-(4-(5,7-Difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazin-1-yl)ethanone

Participants

Reaction Steps

The 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)-quinolin-4-amine (50 mg, 0.11 mmol) was dissolved in THF (1.1 mL) and the triethylamine (24.0 μL, 0.17 mmol) and acetic anhydride (11.0 μL, 0.11 mmol) were added and the mixture was stirred overnight. The reaction was then quenched with water and extracted with EtOAc. The organic layers were dried over magnesium sulfate and the filtrate was cond. The crude material was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 95% over 20 min to provide, after treatment with sodium bicarbonate 1-(4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazin-1-yl)ethanone: 1H NMR (CDCl3) δ ppm 8.22 (1H, d, J=7.6 Hz), 7.88 (1H, d, J=2.2 Hz), 7.82 (1H, d, J=1.8 Hz), 7.49 (1H, dd, J=9.6, 1.2 Hz), 7.14-7.23 (1H, m), 6.86 (1H, ddd, J=13.0, 8.4, 2.3 Hz), 3.77-3.95 (6H, m), 3.61-3.76 (4H, m), 3.53-3.61 (2H, m), 3.23-3.37 (4H, m), 2.19 (3H, s), 2.16 (3H, s). Mass Spectrum (ESI) m/e=483.3 (M+1).

Provenance & Evidence