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

HRID 865496

Reaktionsgleichung

Reaktionsgleichung von HRID 865496
[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-3d9257ae951d4b19a876d8321f7b92de
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565614

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