2,6-Dimethylmorpholine → 6-Chloro-1-cyclopropyl-7-(2,6-dimethylmorpholin-4-yl)-8-fluoro-4-oxo-quinoline-3-carboxylic acid

HRID 2379565

Reaktionsgleichung

Reaktionsgleichung von HRID 2379565
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([CH:14]1[CH2:16][CH2:15]1)[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[C:5]2=[O:20].[CH3:21][CH:22]1[O:27][CH:26]([CH3:28])[CH2:25][NH:24][CH2:23]1.N12CCC(CC1)CN2>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[N:24]1[CH2:23][CH:22]([CH3:21])[O:27][CH:26]([CH3:28])[CH2:25]1)[N:8]([CH:14]1[CH2:16][CH2:15]1)[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[C:5]2=[O:20]

Komponenten

5

Edukt 3

HCID 1108622,6-DimethylmorpholineHCID 136165Diazabicyclo(2.2.2)octaneHCID 135791636-Chloro-1-cyclopropyl-7,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Produkt 1

HCID 4831066-Chloro-1-cyclopropyl-7-(2,6-dimethylmorpholin-4-yl)-8-fluoro-4-oxo-quinoline-3-carboxylic acidAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

3 g (10 mmol) of the product from Example A in 35 ml of dimethyl sulphoxide are heated at 140° with 1.2 g (10 mmol) of 2,6-dimethylmorpholine and 2.2 g (20 mmol) of diazabicyclo[2.2.2]octane for 5 hours. The mixture is concentrated under high vacuum, stirred with 30 ml of water, the pH is adjusted to 6 with 2N hydrochloric acid, and the precipitate is filtered off with suction and recrystallised from glycol monomethyl ether. 1.6 g (41% of theory) of 6-chloro-1-cyclopropyl-8-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-morpholinyl)-4-oxo-3-quinolinecarboxylic acid of melting point 258°-261° (with decomposition) is obtained.

Aufarbeitung

  1. concentrationThe mixture is concentrated under high vacuum
  2. filtrationthe precipitate is filtered off with suction
  3. customrecrystallised from glycol monomethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c33a255ec4fd47a2a356fe93009fb8f1
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05362909

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