Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate → Ethyl 1-[6-(t-butylamino)-3,5-difluoropyridin-2-yl]-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 368397Notes

Reaction equation

HRID 368397 reaction equation
C(O[CH:4]=[C:5]([C:11](=[O:22])[C:12]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([F:20])[C:13]=1F)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.FC1C(F)=C(F)C(F)=CC=1C(CC(OCC)=O)=O.[NH2:41][C:42]1[C:47]([F:48])=[CH:46][C:45]([F:49])=[C:44]([NH:50][C:51]([CH3:54])([CH3:53])[CH3:52])[N:43]=1.NC(=C)C([O-])=O>C(Cl)(Cl)Cl>[C:51]([NH:50][C:44]1[N:43]=[C:42]([N:41]2[C:13]3[C:12](=[CH:17][C:16]([F:18])=[C:15]([F:19])[C:14]=3[F:20])[C:11](=[O:22])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4]2)[C:47]([F:48])=[CH:46][C:45]=1[F:49])([CH3:54])([CH3:52])[CH3:53]

Participants

6

Reactant 4

HCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 15896287N2-(tert-butyl)-3,5-difluoropyridine-2,6-diamineHCID 220225792-AminoacrylateHCID 54346083Ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate

Product 1

HCID 15434900Ethyl 1-[6-(t-butylamino)-3,5-difluoropyridin-2-yl]-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

To 1 ml chloroform solution of ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate prepared from 0.27 g of ethyl 2,3,4,5-tetrafluorobenzoylacetate by normal process was added 2-amino-6-(t-butylamino)-3,5-difluoropyridine until completion of the conversion into the aminoacrylate form was confirmed by monitoring the reaction by TLC. The solution was concentrated under reduced pressure. To the residue were added 0.6 g of anhydrous potassium carbonate and 1 ml of N,N-dimethylformamide, and the mixture was stirred at 90° C. for 15 minutes 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, concentrated under reduced pressure, and allowed to stand. The precipitate was collected by filtration, washed with ethanol and diisopropylether successively to obtain 0.15 g of the title compound as a colorless powder.

Workup

  1. customthe reaction by TLC
  2. concentrationThe solution was concentrated under reduced pressure
  3. additionTo the residue were added 0.6 g of anhydrous potassium carbonate and 1 ml of N,N-dimethylformamide
  4. temperatureto cool
  5. customThe solution was separated
  6. additionby adding 30 ml of chloroform and 300 ml of distilled water
  7. washthe chloroform layer was washed twice with 300 ml of distilled water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-6582fcae3d52485c945dca84e632bbc7
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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