Acetate → 1-(6-Amino-3-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368514Notes

Reaction equation

HRID 368514 reaction equation
Cl.C([O-])(=O)C.[F:6][C:7]1[C:8]([N:22]2[C:31]3[C:26](=[CH:27][C:28]([F:34])=[C:29]([F:33])[C:30]=3[Cl:32])[C:25](=[O:35])[C:24]([C:36]([O:38]CC)=[O:37])=[CH:23]2)=[N:9][C:10]([NH:13]C(C)(C)CC(C)(C)C)=[CH:11][CH:12]=1>>[NH2:13][C:10]1[N:9]=[C:8]([N:22]2[C:31]3[C:26](=[CH:27][C:28]([F:34])=[C:29]([F:33])[C:30]=3[Cl:32])[C:25](=[O:35])[C:24]([C:36]([OH:38])=[O:37])=[CH:23]2)[C:7]([F:6])=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 175AcetateHCID 313Hydrochloric AcidHCID 22121174Ethyl 1-[3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridin-2-yl]-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212881-(6-Amino-3-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 85.1%

Procedure

To 1.2 ml of the mixed solution of 4N hydrochloric acid and acetate (1:1) was added 235 mg of ethyl 1-[3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine-2-yl]-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate and the mixture was heated under reflux for 6 hours with stirring and allowed to cool. The precipitate was collected by filtration and washed with ethanol to obtain 145 mg of the title compound as a gray powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-20d2b16cc2144427b3efe9911def9386
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

Loading…