Water → HCID 19434841, compound

HRID 1736204Notes

Reaction equation

HRID 1736204 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.[CH2:37]([NH:39][CH2:40][CH3:41])[CH3:38].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:37]([N:39]([CH2:40][CH3:41])[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]([CH3:20])([CH3:22])[CH3:21])=[C:13]([F:24])[CH:12]=3)[O:10][C:5]=2[C:4]([F:36])=[CH:3][C:2]=1[F:1])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 8021Diethylamine2×HCID 11430Potassium Carbonate2×HCID 19435004HCID 19435004, compound

Product 1

HCID 19434841HCID 19434841, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3.50 g (6.65 mmol) 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 100 mL of dimethylformamide under argon atmosphere, 6.88 mL (66.5 mmol) of diethylamine and 9.18 g (66.5 mmol) of potassium carbonate were added and the mixture was stirred at 50° C. for 7 hours. Then, 6.88 mL (66.5 mmol) of diethylamine and 9.18 g (66.5 mmol) of potassium carbonate were further added and the mixture was stirred at 50° C. for 16 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=100:1-9:1) to give 1.68 g of 5-(3-diethylaminopropylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one (yield: 50%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 16 hours
  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:methanol=100:1-9:1)

Sources & evidence

ORD record
ord-a0cd89b1b62643dba0f5b02db8a59f8a
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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