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

HRID 373527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373527
[CH2:1]([NH:8][C:9]1[C:18]([F:19])=[C:17](F)[CH:16]=[C:15]2[C:10]=1[C:11](=[O:27])[C:12]([C:24]([OH:26])=[O:25])=[CH:13][N:14]2[CH:21]1[CH2:23][CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH:32]1[CH3:37])(=[O:30])[CH3:29]>N1C=CC=CC=1>[C:28]([N:31]1[CH2:36][CH2:35][N:34]([C:17]2[CH:16]=[C:15]3[C:10]([C:11](=[O:27])[C:12]([C:24]([OH:26])=[O:25])=[CH:13][N:14]3[CH:21]3[CH2:23][CH2:22]3)=[C:9]([NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:18]=2[F:19])[CH2:33][CH:32]1[CH3:37])(=[O:30])[CH3:29]

Komponenten

4

Edukt 2

HCID 148802085-Benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 157294091-(2-Methylpiperazin-1-yl)ethan-1-one

Produkt 1

HCID 198106217-(4-Acetyl-3-methyl-1-piperazinyl)-5-benzylamino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 5-benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1-acetyl-2-methylpiperazine and pyridine was heated under reflux. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with chloroform. The extract was dried and chloroform was evaporated. Ethanol was added to the residue, and the crystals were collected by filtration to give 7-(4-acetyl-3-methyl-1-piperazinyl)-5-benzylamino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. It was recrystallized from ethanol/diisopropyl ether. m.p. 235°-236° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with chloroform
  6. customThe extract was dried
  7. customchloroform was evaporated
  8. additionEthanol was added to the residue
  9. filtrationthe crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-6f70d3e97d024bb8b1fb7792cd699205
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164392

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