1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 19763611, compound

HRID 248530Notes

Reaction equation

HRID 248530 reaction equation
[F:1][CH:2]([F:9])[CH:3]1[NH:8][CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:10]([N:12]1[C:21]2[C:16](=[CH:17][C:18]([F:24])=[C:19](F)[C:20]=2[F:22])[C:15](=[O:25])[C:14]([C:26]([OH:28])=[O:27])=[CH:13]1)[CH3:11]>N1C=CC=CC=1>[F:1][CH:2]([F:9])[CH:3]1[NH:8][CH2:7][CH2:6][N:5]([C:19]2[C:20]([F:22])=[C:21]3[C:16]([C:15](=[O:25])[C:14]([C:26]([OH:28])=[O:27])=[CH:13][N:12]3[CH2:10][CH3:11])=[CH:17][C:18]=2[F:24])[CH2:4]1

Participants

4

Reactant 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19763572HCID 19763572, compound

Product 1

HCID 19763611HCID 19763611, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The above 100 mg of 3-difluoromethylpiperazine and 200 mg of 1-ethyl-1,4-dihydro-6,7,8-trifluoro-4-oxo-3-quinolinecarboxylic acid in 5 ml of pyridine was stirred at 75° C. overnight, then cooled and the solvent- removed in vacuo. The residue was triturated in a hot methanol/chloroform mixture and then purified by chromatography on silica gel, eluting with methanol:dichloromethane (5:95), giving 90 mg of the desired product, mp 212°-227° C. (dec.)

Workup

  1. temperaturecooled
  2. customthe solvent- removed in vacuo
  3. customThe residue was triturated in a hot methanol/chloroform mixture
  4. custompurified by chromatography on silica gel
  5. washeluting with methanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-1efff503f0e445d5bff713f0a95dc07a
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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