7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839374, compound

HRID 2165631Notes

Reaction equation

HRID 2165631 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.Cl[C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]2[CH2:24][CH3:25])=[CH:16][C:15]=1[F:30]>N1C=CC=CC=1>[CH2:24]([N:21]1[C:22]2[C:17](=[CH:16][C:15]([F:30])=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH:7]([C:5]4[S:6][C:2]([CH3:1])=[CH:3][CH:4]=4)[CH2:12]3)[CH:23]=2)[C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20]1)[CH3:25]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197635932-(5-Methylthiophen-2-yl)piperazine

Product 1

HCID 14839374HCID 14839374, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.368 g of 2-(5-methyl-2-thienyl)piperazine and 2.152 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 15 ml of pyridine was heated at reflux under argon for 18 hours, then allowed to cool and the solvent removed. The residue was triturated with methanol and ether, then filtered and dried, giving 580 mg of the desired product, mp 200°-210° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 18 hours
  3. temperatureto cool
  4. customthe solvent removed
  5. customThe residue was triturated with methanol and ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-5307318bacbc4335991a47c57f360f4c
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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