4-Methylmorpholine → HCID 22050145, compound

Participants

Reaction Steps

1-[3-(aminomethyl)benzyl]-3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (EXAMPLE 161) (0.300 g, 0.668 mmol), 1-hydroxyisobutyric acid (0.215 g, 2.064 mmol), 1-hydroxybenzotriazole (0.112 g, 0.826 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.185 g, 0.963 mmol) were dissolved in N,N-dimethylacetamide (3 mL). N-methylmorpholine (0.209 g, 2.064 mmol) was added, and the reaction stirred for 1 hour at room temperature. The reaction was diluted with H2O (50 mL) and the aqueous layer extracted with ethyl acetate (3×25 mL). The combined organics were then washed with 1N HCl (25 mL), saturated Na2CO3 (25 mL), brine (25 mL), dried over Na2SO4, and concentrated to yield an off-white solid (0.235 g, 64%). 1H NMR (400 MHz, DMF-d6) δ 8.25 (br s, 1H), 7.81 (app q, J=7.92 Hz, 1H), 7.40-7.21 (m, 5H), 7.09 (d, J=6.84 Hz, 1H), 6.67 (s, 1H), 5.46 (s, 2H), 5.42 (s, 2H), 4.42 (d, J=6.24 Hz, 2H), 2.44 (s, 3H), 1.38 (s, 6H). ES-HRMS m/z 535.1024 (M+H C25H25BrF2N2O4 requires 535.1039).

Provenance & Evidence