1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1589564

Reaktionsgleichung

Reaktionsgleichung von HRID 1589564
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].Cl.Cl.[CH:21]12[CH2:28][CH2:27][CH:24]([NH:25][CH2:26]1)[CH2:23][NH:22]2.N12CCCN=C1CCCCC2>C(#N)C>[CH:21]12[CH2:28][CH2:27][CH:24]([NH:25][CH2:26]1)[CH2:23][N:22]2[C:10]1[CH:11]=[C:12]2[C:7]([C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4][N:3]2[CH2:1][CH3:2])=[CH:8][C:9]=1[F:14]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 229243902,5-Diazabicyclo(2.2.2)octane dihydrochloride

Produkt 1

HCID 135657957-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 0.52 g (2.0 mmole) of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.37 g (2.0 mmole) of 2,5-diazabicyclo(2.2.2)octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 0.90 ml (6.0 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 25 ml of acetonitrile was heated under reflux for 21 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was recrystallized from ethanol to give 0.30 g of the title compound, mp 270°-272°.

Aufarbeitung

  1. temperatureunder reflux for 21 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9cd97c866e664a92aa9f435b7db69aaf
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04571396

Verknüpfte Notizen

Wird geladen…