2-Methylpiperazine → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-4-oxo-

HRID 2291275

Reaktionsgleichung

Reaktionsgleichung von HRID 2291275
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[CH3:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:27]2[CH2:26][CH2:25][NH:24][CH:23]([CH3:22])[CH2:28]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Komponenten

4

Edukt 2

HCID 660572-MethylpiperazineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Produkt 1

HCID 30666843-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-4-oxo-Ausbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.25 g), 2-methylpiperazine (2.0 g), and pyridine (13 ml) was heated at 105°-110° C. for 1 hour with stirring. The reaction mixture was evaporated to dryness under reduced pressure and water was added to the residue. The mixture was extracted with chloroform and the extract was dried. After evaporation of chloroform, ethanol was added to the residue. The resulting crystals were filtered and recrystallized from chloroform-ethanol to give 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.4 g), m.p. 251°-253° C.

Aufarbeitung

  1. temperaturewas heated at 105°-110° C. for 1 hour
  2. customThe reaction mixture was evaporated to dryness under reduced pressure and water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with chloroform
  5. customthe extract was dried
  6. customAfter evaporation of chloroform, ethanol
  7. additionwas added to the residue
  8. filtrationThe resulting crystals were filtered
  9. customrecrystallized from chloroform-ethanol

Quellen und Nachweise

ORD-Eintrag
ord-7575f8ad516d41479d5f0b19a63d9fe6
Quelldatensatz
uspto-grants-1989_01
Patentnummer
US04795751

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