1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → (+)-1-Ethyl-6,8-difluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165653
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[F:20][CH2:21][CH:22]1[NH:27][CH2:26][CH2:25][NH:24][CH2:23]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:24]3[CH2:25][CH2:26][NH:27][CH:22]([CH2:21][F:20])[CH2:23]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14479501HCID 14479501, Verbindung

Produkt 1

HCID 14839398(+)-1-Ethyl-6,8-difluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 500 mg of 1-ethyl-1,4-dihydro-6,7,8-trifluoro-4-oxo-3-quinolinecarboxylic acid, 650 mg of racemic 3-fluoromethylpiperazine and 5 ml of pyridine was stirred at 80° C. in a sealed bottle under nitrogen for 2.5 hours. The solvents were removed and the residue triturated with methanol. The solid was collected, washed with methanol and dried, giving 376 mg of the desired product, mp 230°-235° C. (dec.).

Aufarbeitung

  1. customThe solvents were removed
  2. customthe residue triturated with methanol
  3. customThe solid was collected
  4. washwashed with methanol
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-83727a4b9d124551ad67a055d4161182
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04940710

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