1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 19763575, compound

HRID 248511Notes

Reaction equation

HRID 248511 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][C:3]=1[CH:8]1[CH2:13][NH:12][CH2:11][CH2:10][NH:9]1.C([N:16]1[C:25]2[C:20](=[CH:21][C:22]([F:27])=[C:23](F)[CH:24]=2)[C:19](=[O:28])[C:18]([C:29]([OH:31])=[O:30])=[CH:17]1)C>N1C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][C:3]=1[CH:8]1[NH:9][CH2:10][CH2:11][N:12]([C:23]2[CH:24]=[C:25]3[C:20]([C:19](=[O:28])[C:18]([C:29]([OH:31])=[O:30])=[CH:17][NH:16]3)=[CH:21][C:22]=2[F:27])[CH2:13]1

Participants

4

Reactant 2

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197635852-(3,5-Dimethylfuran-2-yl)piperazine

Product 1

HCID 19763575HCID 19763575, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 1.4 g of 2-(3,5-dimethyl-2-furanyl)piperazine was dissolved in 5 ml of pyridine, 0.66 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid added and the mixture heated at 95°-100° C., under argon, :n a pressure bottle for 4 hours, then cooled. The solvent was removed in vacuo, the residue evaporated twice from toluene and the residue chromatographed, giving 700 mg of crude product. This product was recrystallized from methanol, giving 220 mg of the desired product, mp 230°-232° C.

Workup

  1. temperaturethe mixture heated at 95°-100° C., under argon
  2. temperaturecooled
  3. customThe solvent was removed in vacuo
  4. customthe residue evaporated twice from toluene
  5. customthe residue chromatographed
  6. customgiving 700 mg of crude product
  7. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-e8b05760f66f4e949a4a1328125df993
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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