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

HRID 2379565

Reaction equation

HRID 2379565 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c33a255ec4fd47a2a356fe93009fb8f1
Source dataset
uspto-grants-1994_11
Patent number
US05362909

Linked notes

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