Water → HCID 19434947, compound

HRID 1736205Notes

Reaction equation

HRID 1736205 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.[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[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]([CH3:21])([CH3:22])[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][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 19435004HCID 19435004, compound

Product 1

HCID 19434947HCID 19434947, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

709 mg (1.35 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 30 mL of dimethylformamide under argon atmosphere, 1.14 mL (13.5 mmol) of pyrrolidine and 1.86 g (13.5 mmol) of potassium carbonate were added and the mixture was stirred at 50° C. for 8 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=100:9:1) to give 431 mg of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-[3-(pyrrolidin-1-yl)propylamino]-4H-1-benzopyran-4-one (yield: 64%).

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=100:9:1)

Sources & evidence

ORD record
ord-b34843dbd2914e4d8760a659317fe7ff
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

Loading…