1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[5-(phenylmethyl)-2,5-diazabicyclo(2.2.1)hept-2-yl]-3-quinolinecarboxylic acid

HRID 1589572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589572
[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].Br.Br.[C:22]1([CH2:28][N:29]2[CH2:34][CH:33]3[CH2:35][CH:30]2[CH2:31][NH:32]3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N12CCCN=C1CCCCC2>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:32]3[CH2:31][CH:30]4[CH2:35][CH:33]3[CH2:34][N:29]4[CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH: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

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 166374642-Benzyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide

Produkt 1

HCID 135658241-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[5-(phenylmethyl)-2,5-diazabicyclo(2.2.1)hept-2-yl]-3-quinolinecarboxylic acidAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 0.54 g (2.0 mmol) of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.77 g (2.2 mmol) of 5-(phenylmethyl)-2,5-diazabicyclo(2.2.1)heptane dihydrobromide, (P. S. Portoghese and A. A. Mikhail, J. Org. Chem. 31, 1059 (1966)], 0.90 ml (6.0 mmol) of 1,8-diazabicyclo(5.4.0)undec-7-ene, and 20 ml of acetonitrile was heated under reflux for two hours and stirred at room temperature for two days. The mixture was filtered and the solid was washed with methanol to give 0.44 g of the title compound, mp 195°-198° C.

Aufarbeitung

  1. temperatureunder reflux for two hours
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-01c1a2ba7b6545648357dee5608857ad
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04571396

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