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

HRID 248484Notes

Reaction equation

HRID 248484 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-e075c6392e1c43729f415a6b2808cbf7
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

Loading…