Acetic Acid → 1-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 2235039Notes

Reaction equation

HRID 2235039 reaction equation
[Br:1][C:2]1[C:3]([F:32])=[C:4]([F:31])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[C:14]([NH:20]C(C)(C)C)[N:13]=1)[CH:9]=[C:8]([C:25]([O:27]CC)=[O:26])[C:7]2=[O:30].Cl.C(O)(=O)C>O>[NH2:20][C:14]1[N:13]=[C:12]([N:10]2[C:11]3[C:6](=[CH:5][C:4]([F:31])=[C:3]([F:32])[C:2]=3[Br:1])[C:7](=[O:30])[C:8]([C:25]([OH:27])=[O:26])=[CH:9]2)[C:17]([F:18])=[CH:16][C:15]=1[F:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 15434899Ethyl 8-bromo-1-[6-(t-butylamino)-3,5-difluoro-pyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 154869771-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 8-bromo-1-[6-(tert-butylamino)-3,5-difluoropyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinolin-3-carboxylate (1.38 g) was added to a liquid mixture of 14% hydrochloric acid (3.5 mL) and acetic acid (3.5 mL), followed by stirring for five hours under reflux. Distilled water (5 mL) was added to the mixture, and the mixture was left to cool. The precipitate was collected through filtration, and washed sequentially with ethanol and diisopropyl ether, to thereby yield 1.10 g of the title compound as a colorless powder.

Workup

  1. temperatureunder reflux
  2. waitthe mixture was left
  3. temperatureto cool
  4. filtrationThe precipitate was collected through filtration
  5. washwashed sequentially with ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-382b36284419445996453e5f81424842
Source dataset
uspto-grants-2010_05
Patent number
US07713997B2

Reaction notes

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