7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839382, compound

HRID 2165639Notes

Reaction equation

HRID 2165639 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:13])=[CH:5][C:6]=1[CH:7]1[CH2:12][NH:11][CH2:10][CH2:9][NH:8]1.Cl[C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:30])[C:20]([C:27]([OH:29])=[O:28])=[CH:21][N:22]2[CH2:25][CH3:26])=[CH:17][C:16]=1[F:31]>N1C=CC=CC=1>[Cl:1][C:2]1[S:3][C:4]([Cl:13])=[CH:5][C:6]=1[CH:7]1[NH:8][CH2:9][CH2:10][N:11]([C:15]2[CH:24]=[C:23]3[C:18]([C:19](=[O:30])[C:20]([C:27]([OH:29])=[O:28])=[CH:21][N:22]3[CH2:25][CH3:26])=[CH:17][C:16]=2[F:31])[CH2:12]1

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19763570HCID 19763570, compound

Product 1

HCID 14839382HCID 14839382, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3.1 g portion of 2-(2,5-dichloro-3-thienyl)piperazine was dissolved in 8 ml of pyridine, 880 mg of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added and the mixture was heated, under argon, in a pressure bottle, at 120°-130° C. for 18 hours. After cooling, the solid was collected, washed with ethanol, dried and recrystallized from dimethylformamide, giving 171 mg of the desired product, mp 254°-256° C. (dec.).

Workup

  1. temperaturethe mixture was heated, under argon, in a pressure bottle, at 120°-130° C. for 18 hours
  2. temperatureAfter cooling
  3. customthe solid was collected
  4. washwashed with ethanol
  5. customdried
  6. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-bf616b52a6bb433a875d5fdd83e4d043
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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