Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate → Ethyl 1-[3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridin-2-yl]-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Temperature

90 °C

To 3 ml chloroform solution of ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate prepared from 0.84 g of ethyl 3-chloro-2,4,5-trifluorobenzoylacetate by normal process was added 0.75 g of 2-amino-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine. The solution was concentrated under reduced pressure, and to the residue were added 0.65 g of anhydrous potassium carbonate and 1.5 ml of N,N-dimethylformamide, and the mixture was stirred at 90° C. for 1 hour and allowed to cool. The solution was separated by adding 30 ml of chloroform and 300 ml of distilled water, and the chloroform layer was washed twice with 300 ml of distilled water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 0.45 g of the title compound as a pale yellow powder.

1. concentrationThe solution was concentrated under reduced pressure
2. additionto the residue were added 0.65 g of anhydrous potassium carbonate and 1.5 ml of N,N-dimethylformamide
3. temperatureto cool
4. customThe solution was separated
5. additionby adding 30 ml of chloroform and 300 ml of distilled water
6. washthe chloroform layer was washed twice with 300 ml of distilled water
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. filtrationThe precipitate was collected by filtration
10. washwashed with ethanol and diisopropylether successively

ORD record

ord-e28a309c2f7e48508059ef8b6865f25a

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133284