Water → 2-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one

HRID 1736172Notes

Reaction equation

HRID 1736172 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])=[C:20]([CH3:23])[C:19]([F:24])=[C:18]([NH2:25])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:26])(=[O:3])[CH3:2].[H-].[Na+].I[CH2:30][CH2:31][CH3:32].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])=[C:20]([CH3:23])[C:19]([F:24])=[C:18]([NH2:25])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:26])[CH2:30][CH2:31][CH3:32])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 194349512-(4-acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one

Product 1

HCID 194348902-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

506 mg (1.40 mmol) of the above 2-(4-acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one was dissolved in 30 mL of dimethylformamide under argon atmosphere, 60 mg (1.5 mmol) of sodium hydride (60% oil dispersion) and 0.28 mL (2.8 mmol) of 1-iodopropane were added thereto under ice-cooling and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction solution and the mixture was extracted twice 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) to give 315 mg of 2-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one (yield: 56%).

Workup

  1. temperatureunder ice-cooling
  2. extractionthe mixture was extracted twice 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)

Sources & evidence

ORD record
ord-3b0a941f81e74c6da145b0f1e73bdf3d
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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