7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839376, compound

HRID 2165632Notes

Reaction equation

HRID 2165632 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)[S:5][CH:6]=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:4]4[S:5][CH:6]=[C:2]([CH3:1])[CH:3]=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 197636002-(4-Methylthiophen-2-yl)piperazine

Product 1

HCID 14839376HCID 14839376, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 10.92 g of 2-(4-methyl-2-thienyl)piperazine and 5.38 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 30 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 2 g of the desired product, mp 230° C.

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-f8917d294ae4444eb5429387adc69f93
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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