HCID 16122022, compound → HCID 21862598, compound

Temperature

90 °C

Sodium methylate methanol solution (28%, 96 g, 0.50 mol) was added to a solution of 2-(2-benzoylaminophenyl)-2-cyanoacetamide (Reference compound 17-1, 30 g, 0.11 mol) in anhydrous methanol (200 mL), and the mixture was stirred at 90° C. for 4.5 hours. The reaction mixture was concentrated by half in the volume under reduced pressure. After ice-water (500 mL) was added to the mixture, the whole was extracted with ethyl acetate (400 mL×2). The organic layer was washed with brine (300 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, ethanol (400 mL) was added to the residue and the insoluble solid was removed by filtration. After the filtrate was concentrated under reduced pressure, chloroform (80 mL) was added to the residue and the precipitated solid was washed with diethyl ether (40 mL). The resultant solid was dried under reduced pressure to give the title reference compound (10 q) as a brown solid (yield 53%).

1. concentrationThe reaction mixture was concentrated by half in the volume under reduced pressure
2. additionAfter ice-water (500 mL) was added to the mixture
3. extractionthe whole was extracted with ethyl acetate (400 mL×2)
4. washThe organic layer was washed with brine (300 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. customAfter the solvent was evaporated under reduced pressure, ethanol (400 mL)
7. additionwas added to the residue
8. customthe insoluble solid was removed by filtration
9. concentrationAfter the filtrate was concentrated under reduced pressure, chloroform (80 mL)
10. additionwas added to the residue
11. washthe precipitated solid was washed with diethyl ether (40 mL)
12. customThe resultant solid was dried under reduced pressure

ORD record

ord-ed8079245bb740fa9b6228f129a7979c

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193237B2