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 368501Notes

Reaction equation

HRID 368501 reaction equation
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

Participants

5

Reactant 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

Product 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-carboxylateYield 65.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c5cc779034804bdab6ac6becf502a3b8
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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