Water → HCID 19434852, compound

HRID 1736203Notes

Reaction equation

HRID 1736203 reaction equation
[F:1][C:2]1[CH:3]=[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.[CH3:38][NH:39][CH3:40].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:38][N:39]([CH3:40])[CH2:30][CH2:29][CH2:28][NH:27][C:26]1[C:6]2[C:7](=[O:25])[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:22])[CH3:20])=[C:13]([F:24])[CH:12]=3)[O:10][C:5]=2[C:4]([F:36])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 19435004HCID 19435004, compound

Product 1

HCID 19434852HCID 19434852, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

709 mg (1.35mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-(3-methanesulfonyloxypropylamino)-4H-1-benzopyran-4-one obtained in Example 129 (2) was dissolved in 30 mL of dimethylformamide under argon atmosphere, 1.10 g (13.5 mmol) of dimethylamine hydrochloride and 1.86 g (13.5 mmol) of potassium carbonate were added and the mixture was stirred at 50° C. for 39 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:methanol=100:1) to give 444 mg of 5-(3-dimethylaminopropylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one (yield: 69%).

Workup

  1. extractionthe mixture was extracted twice 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)

Sources & evidence

ORD record
ord-a7d93f0f7aa7491f952eb38770339577
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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