Ethyl Acetate → HCID 58043585, compound

Temperature

100 °C

To a solution of 5-(3-(4-bromophenyl)-3-(2,4-difluorophenyl)propanoyl)-1-methyl-pyridin-2(1H)-one (0.2 g, 463 μmol) in ethanol (5 mL) and water (0.2 mL) was added hydroxylamine hydrochloride (80.4 mg, 1.16 mmol) and sodium hydrogencarbonate (77.7 mg, 925 μmol) and the resulting colourless suspension was heated at reflux (100° C. oil bath temperature) for 4.5 hours. After cooling down the reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Colourless foam (0.205 g, 99%). MS (ESI+): m/z=449.1 ([M+H]+).

1. temperaturethe resulting colourless suspension was heated
2. temperatureAfter cooling down the reaction mixture
3. customthe layers were separated
4. extractionThe aqueous layer was extracted twice with ethyl acetate
5. washThe organic layers were washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. additiontreated with silica gel
9. customevaporated
10. customThe compound was purified by silica gel chromatography on a 20 g column
11. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)

ORD record

ord-824049f3a413410e936ed9c2e4328ec8

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765730B2