Potassium Carbonate → Ethyl 1-(4-amino-5-fluoropyridine-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 610238Notes

Reaction equation

HRID 610238 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([NH:9][CH:10]=[C:11]([C:17](=[O:28])[C:18]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([Cl:26])[C:19]=2F)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1.NC1C=C(NC=C(C(=O)C2C=C(F)C(F)=C(Cl)C=2F)C(OCC)=O)C(F)=CN=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([N:9]2[C:19]3[C:18](=[CH:23][C:22]([F:24])=[C:21]([F:25])[C:20]=3[Cl:26])[C:17](=[O:28])[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10]2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178471951HCID 178471951, compoundHCID 178471955HCID 178471955, compound

Product 1

HCID 22121193Ethyl 1-(4-amino-5-fluoropyridine-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 150 mg of the mixture of ethyl 3-(4-amino-5-fluoropyridin-2-yl)amino-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate and ethyl 3-(2-amino-5-fluoropyridin-4-yl)amino-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate were added 230 mg of anhydrous potassium carbonate and 450 mg of N,N-dimethylformamide, and the mixture was stirred at 100° C. for 20 minutes and allowed to cool. The solution was separated by adding 20 ml of chloroform and 100 ml of distilled water, and the chloroform layer was washed with 100 ml of distilled water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel, 3.2 g; eluent: chloroform:methanol, 100:1), and the fraction containing the main product was concentrated under reduced pressure to obtain 35 mg of the title compound as a yellow solid residue.

Workup

  1. temperatureto cool
  2. customThe solution was separated
  3. additionby adding 20 ml of chloroform and 100 ml of distilled water
  4. washthe chloroform layer was washed with 100 ml of distilled water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionthe fraction containing the main product
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-603b60ef70ab42329cb2235d3f31155b
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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