Triethylamine → 1-Cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651411
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.Cl.Cl.[CH3:22][N:23]([CH3:28])[CH:24]1[CH2:27][NH:26][CH2:25]1.C(N(CC)CC)C>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:26]4[CH2:27][CH:24]([N:23]([CH3:28])[CH3:22])[CH2:25]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 8471TriethylamineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 22121220N,N-dimethylazetidin-3-amine dihydrochloride

Produkt 1

HCID 100431761-Cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Versuchsvorschrift

A mixture of 0.25 g (1.32 mmoles) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.34 g (12 mmoles) of 3-dimethylaminoazetidine dihydrochloride and 3.3 g (33 mmoles) of triethylamine is heated under reflux in 10 ml of pryidine for 2 hours. The mixture is evaporated under vacuum, water is added and the resulting mixture made alkaline with 1N sodium hydroxide, heated, filtered while hot, acidified with acetic acid and filtered again. After washing with water, 0.4 g (88%) of 1-cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 255°-61° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux in 10 ml of pryidine for 2 hours
  3. customThe mixture is evaporated under vacuum, water
  4. additionis added
  5. temperatureheated
  6. filtrationfiltered while hot,
  7. filtrationfiltered again
  8. washAfter washing with water, 0.4 g (88%) of 1-cyclopropyl-6-fluoro-7-(3-dimethylamino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  9. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-b155683b214249d5ac0aec0dd0b8c0d3
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927926

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