Ethyl bromoacetate → HCID 86633058, compound

HRID 1094188Notes

Reaction equation

HRID 1094188 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:22])[C:13]([OH:21])=[CH:14][N:15]3[CH:18]([CH3:20])[CH3:19])=[CH:10][C:9]=2[F:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].[Cl-].[NH4+]>CN(C=O)C>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:22])[C:13]([O:21][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:14][N:15]3[CH:18]([CH3:20])[CH3:19])=[CH:10][C:9]=2[F:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 57811578HCID 57811578, compound

Product 1

HCID 86633058HCID 86633058, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 5.0 ml DMF solution of 144 mg of 7-(cyclohexylamino)-6-fluoro-3-hydroxy-1-isopropylquinolin-4(1H)-one were added 313 mg of potassium carbonate and 100 μl of ethyl bromoacetate in that order, followed by overnight stirring at room temperature. Aqueous saturated ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. After drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure, the residue was purified by silica gel column chromatography to obtain 159 mg of ethyl {[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]oxy}acetate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialAfter drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d5c5b0aafa54ccc8d4b19ec28e6eb0c
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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