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

HRID 368501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368501
C1(C)C=CC=CC=1.[F:8][C:9]1[C:10]([N:26]2[C:35]3[C:30](=[C:31](F)[C:32]([F:38])=[C:33]([F:37])[C:34]=3[F:36])[C:29](=[O:40])[C:28]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:27]2)=[N:11][C:12]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:13]([F:15])[CH:14]=1.[CH2:46]([NH2:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CCCCCC>[CH2:46]([NH:53][C:31]1[C:32]([F:38])=[C:33]([F:37])[C:34]([F:36])=[C:35]2[C:30]=1[C:29](=[O:40])[C:28]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:27][N:26]2[C:10]1[C:9]([F:8])=[CH:14][C:13]([F:15])=[C:12]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:11]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Komponenten

5

Edukt 3

HCID 1140Toluene2×HCID 7504BenzylamineHCID 22121224Ethyl 1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 22121197Ethyl 5-benzylamino-1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To 8 ml of toluene were added 1.58 g of ethyl 1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridine-2-yl]-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate together with 0.68 g of benzylamine, and the mixture was stirred at 110° C. for 20 minutes and allowed to cool. After adding 15 ml of toluene and 15 ml of n-hexane, the mixture was washed twice with 300 ml of distilled water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added 4 ml of ethanol, and the solution was allowed to stand, and the precipitate was collected by filtration and washed with ethanol to obtain 1.20 g of the title compound as a yellow powder.

Aufarbeitung

  1. temperatureto cool
  2. washthe mixture was washed twice with 300 ml of distilled water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added 4 ml of ethanol
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c5cc779034804bdab6ac6becf502a3b8
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133284

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