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

HRID 248467Notes

Reaction equation

HRID 248467 reaction equation
[Br: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>[Br:1][C:2]1[S:6][C:5]([CH:7]2[NH:8][CH2:9][CH2:10][N:11]([C:14]3[CH:23]=[C:22]4[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]4[CH2:24][CH3:25])=[CH:16][C:15]=3[F:30])[CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197636062-(5-Bromothiophen-2-yl)piperazine

Product 1

HCID 148393577-[3-(5-Bromo-2-thienyl)-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3 g portion of 2-(5-bromo-2-thienyl)piperazine was suspended in 8 ml of dry pyridine. An 820 mg portion of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added and the mixture was heated in a pressure bottle, under argon, at 120°-130° C. for 18 hours, then cooled, filtered and evaporated to dryness. The residue was evaporated from toluene and this residue purified by chromatography, eluting with chloroform:water saturated methanol (9:1). The appropriate fractions were combined, evaporated and recrystallized from dimethylformamide-ether, giving 440 mg of the desired product, mp 233°-235° C. (dec.).

Workup

  1. temperaturethe mixture was heated in a pressure bottle, under argon, at 120°-130° C. for 18 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was evaporated from toluene
  6. customthis residue purified by chromatography
  7. washeluting with chloroform
  8. customevaporated
  9. customrecrystallized from dimethylformamide-ether

Sources & evidence

ORD record
ord-62e553e0534042cb81e8b5f28c252a13
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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