5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 7-(4-Acetyl-3-methyl-1-piperazinyl)-5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 373525Notes

Reaction equation

HRID 373525 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1.[C:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH:25]1[CH3:30])(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([N:24]1[CH2:29][CH2:28][N:27]([C:10]2[CH:9]=[C:8]3[C:3]([C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]3[CH:14]3[CH2:16][CH2:15]3)=[C:2]([NH2:1])[C:11]=2[F:12])[CH2:26][CH:25]1[CH3:30])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 148802095-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 157294091-(2-Methylpiperazin-1-yl)ethan-1-one

Product 1

HCID 157294107-(4-Acetyl-3-methyl-1-piperazinyl)-5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1-acetyl-2-methylpiperazine and pyridine was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in aqueous ammonia. The solution was neutralized with an aqueous solution of acetic acid and cooled with ice. The crystals were collected by filtration to give 7-(4-acetyl-3-methyl-1-piperazinyl)-5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. It was recrystallized from ethanol/chloroform. m.p. 269°-271° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in aqueous ammonia
  5. temperaturecooled with ice
  6. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-26324228f0cc4ba489924766c6313cc9
Source dataset
uspto-grants-1992_11
Patent number
US05164392

Reaction notes

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