Water → HCID 19434875, compound

HRID 1736181Notes

Reaction equation

HRID 1736181 reaction equation
[F:1][C:2]1[C:3]([CH3:37])=[C:4]([F:36])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27][CH2:28][CH2:29][CH2:30]OS(C)(=O)=O.Cl.[CH3:39][NH:40][CH3:41].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:1][C:2]1[C:3]([CH3:37])=[C:4]([F:36])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:20])[CH3:21])=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27][CH2:28][CH2:29][CH2:30][N:40]([CH3:41])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 19434955HCID 19434955, compound

Product 1

HCID 19434875HCID 19434875, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1.02 g (1.89 mmol) of the above 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-(3-methanesulfonyloxypropylamino)-7-methyl-4H-1-benzopyran-4-one was dissolved in 30 mL of dimethylformamide, 1.54 g (18.9 mmol) of dimethylamine hydrochloride and 2.60 g (18.9 mmol) of potassium carbonate were added and the mixture was stirred at 50° C. for 24 hours. Water was added to the reaction solution and the mixture was extracted once 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:methanol:=100:1-9:1) to give 660 mg of 6,8-difluoro-5-(3-dimethylaminopropylamino)-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-one (yield: 71%).

Workup

  1. extractionthe mixture was extracted once with ethyl acetate
  2. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol:=100:1-9:1)

Sources & evidence

ORD record
ord-4536bfa461724500b68d75fd2c182ae4
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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