7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-[3-(2,5-Dimethyl-3-thienyl)-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248489Notes

Reaction equation

HRID 248489 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:13])=[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>[CH3:1][C:2]1[S:3][C:4]([CH3:13])=[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 197636102-(2,5-Dimethyl-3-thienyl)piperazine

Product 1

HCID 148393817-[3-(2,5-Dimethyl-3-thienyl)-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 46.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.35 g of 2-(2,5-dimethyl-3-thienyl)piperazine and 1.076 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 10 ml of pyridine was heated for 48 hours, then cooled and filtered. The filtrate was evaporated under reduced pressure and the residue triturated with chloroform:methanol (9:1),. giving 800 mg of the desired product, mp 248°-250° C.

Workup

  1. temperaturewas heated for 48 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue triturated with chloroform:methanol (9:1)

Sources & evidence

ORD record
ord-e7261769215c4cee8c6b9812cfbfa549
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

Loading…