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

HRID 610275Notes

Reaction equation

HRID 610275 reaction equation
F[C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[NH2:20][C:21]1[C:26]([F:27])=[CH:25][C:24]([F:28])=[C:23]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[N:22]=1.[C:39](OCC)(=O)C=C>C(Cl)(Cl)Cl>[F:27][C:26]1[C:21]([N:20]2[C:2]3[C:3](=[C:12]([F:19])[C:13]([F:18])=[C:14]([F:17])[C:15]=3[F:16])[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:39]2)=[N:22][C:23]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[C:24]([F:28])[CH:25]=1

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 2760255Ethyl (pentafluorobenzoyl)acetateHCID 221212562-Amino-3,5-difluoro-6-(p-methoxybenzylamino)pyridine

Product 1

HCID 22121224Ethyl 1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

To 20 ml of chloroform solution of ethyl 3-ethoxy-2-pentafluorobenzoylacrylate prepared from 5.6 g of ethyl 2,3,4,5,6-pentafluorobenzoylacetate by normal process was added 2-amino-3,5-difluoro-6-(p-methoxybenzylamino)pyridine until the disappearance of the ethyl acrylate spot in TLC analysis. The solution was concentrated under reduced pressure. To the residue were added 4.3 g of anhydrous potassium carbonate and 15 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 100 ml of chloroform and 1 liter of distilled water, and the chloroform layer was washed twice with 1 liter of distilled water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was dispersed in ethanol, collected by filtration, and washed with ethanol and diisopropylether successively to obtain 6.15 g of the title compound as a colorless powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionTo the residue were added 4.3 g of anhydrous potassium carbonate and 15 ml of N,N-dimethylformamide
  3. temperatureto cool
  4. customThe solution was separated
  5. additionby adding 100 ml of chloroform and 1 liter of distilled water
  6. washthe chloroform layer was washed twice with 1 liter of distilled water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionThe precipitate was dispersed in ethanol
  10. filtrationcollected by filtration
  11. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-9865e4c6e0bf4a368053e3c3cd1764f6
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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