1-Methylpiperazine → 7-Fluoro-8-(4-methyl-1-piperazinyl)-5-oxo-1,2-dihydro-5H-thiazolo (3,2-a)-quinoline-4-carboxylic acid

HRID 2295719Notes

Reaction equation

HRID 2295719 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:19].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[F:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:24]1[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]1)[N:9]1[CH2:12][CH2:13][S:14][C:8]1=[C:7]([C:15]([OH:17])=[O:16])[C:6]2=[O:18]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 131164168-bromo-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a) quinoline-4-carboxylic acid

Product 1

HCID 100672737-Fluoro-8-(4-methyl-1-piperazinyl)-5-oxo-1,2-dihydro-5H-thiazolo (3,2-a)-quinoline-4-carboxylic acidYield 22%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 500 mg (1.45 mmol) of 8-bromo-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a) quinoline-4-carboxylic acid, 730 mg (7.25 mmol) of N-methylpiperazine and 10 ml of pyridine was heated to reflux for twelve hours on an oil bath. The conent was then concentrated under reduced pressure, water was added to the residue, insoluble matters were collected by filtration, washed with water, dried, and the resulting powder was recrystallized from dimethyl formamide to give 116 mg (22.0 percent) of the title compound. Melting point was 267° to 271° C. (decomposition).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for twelve hours on an oil bath
  3. concentrationThe conent was then concentrated under reduced pressure, water
  4. additionwas added to the residue, insoluble matters
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried
  8. customthe resulting powder was recrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-06c50cd67bf0499dac6fd380f90164ca
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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