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

HRID 2165661Notes

Reaction equation

HRID 2165661 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, in 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, in a pressure bottle for 4 hours
  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-6e38a54d626f414c8bd6753ced82ddae
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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