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

HRID 610266Notes

Reaction equation

HRID 610266 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]([Cl:20])[C:13]=1F)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.ClC1C(F)=C(C=C(F)C=1F)C(CC(OCC)=O)=O.[NH2:41][C:42]1[C:47]([F:48])=[CH:46][C:45]([Cl:49])=[C:44]([NH:50][CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=2)[N:43]=1>C(Cl)(Cl)Cl>[Cl:20][C:14]1[C:15]([F:19])=[C:16]([F:18])[CH:17]=[C:12]2[C:13]=1[N:41]([C:42]1[C:47]([F:48])=[CH:46][C:45]([Cl:49])=[C:44]([NH:50][CH2:51][C:52]3[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=3)[N:43]=1)[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]2=[O:22]

Participants

5

Reactant 3

HCID 10934859Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoateHCID 221212532-Amino-5-chloro-3-fluoro-6-(p-methoxybenzylamino)pyridineHCID 54402571Ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate

Product 1

HCID 22121268Ethyl 8-chloro-1-[5-chloro-3-fluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

To 2 ml chloroform solution of ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate prepared from 0.56 g of ethyl 3-chloro-2,4,5-trifluorobenzoylacetate by normal process was added 0.66 g of 2-amino-5-chloro-3-fluoro-6-(p-methoxybenzylamino)pyridine. The solution was concentrated under reduced pressure. To the residue were added 0.5 g of anhydrous potassium carbonate and 1.5 ml of N,N-dimethylformamide, and the mixture was stirred at 90° C. for 20 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 with 300 ml of distilled water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The solution was allowed to stand after adding 4 ml of ethanol. The precipitate was collected by filtration, washed with ethanol and diisopropylether successively to obtain 0.56 g of the title compound as a pale yellow powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionTo the residue were added 0.5 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 with 300 ml of distilled water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionafter adding 4 ml of ethanol
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-4f92687b036b4508ac83b6c243cc018d
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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