Water → HCID 19434847, compound

HRID 1736124Notes

Reaction equation

HRID 1736124 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])(=[O:3])[CH3:2].[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Br.[H-].[Na+].O>CN(C)C=O>[C:1]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][Br:26])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 194349072-(4-Acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

Product 1

HCID 19434847HCID 19434847, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.00 g (14.4 mmol) of Compound 27 obtained in Example 27 was dissolved in 150 ml of dimethylformamide under argon atmosphere, 10.9 ml of 1,6-dibromohexane and 575 mg of sodium hydride (60% oil dispersion) were added under ice-cooling and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:acetone=20:1) to give 6.11 g (83%) of 2-[4-[N-acetyl-N-(6-bromohexyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:acetone=20:1)

Sources & evidence

ORD record
ord-96ab6806060e4bb18d6837a501f05c34
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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