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

HRID 1274729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1274729
[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

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 178471951HCID 178471951, VerbindungHCID 178471955HCID 178471955, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 150 mg of the mixture of ethyl 3-(4-amino-5-fluoropyridine-2-yl)amino-2-(3-chloro-2,4,5-trifluoro-benzoyl)acrylate and ethyl 3-(2-amino-5-fluoropyridine-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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-eb38112ea5d14e2ab52870d9a4fb4bf1
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156903

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