Water → HCID 19434826, compound

HRID 1736182Notes

Reaction equation

HRID 1736182 reaction equation
[F:1][C:2]1[C:3]([CH3:37])=[C:4]([F:36])[C:5]2O[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=O)[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.[CH2:38]([NH:40][CH2:41][CH3:42])[CH3:39].[OH2:43].[OH-:44].[Na+]>CN(C)C=O>[CH2:38]([N:40]([CH2:41][CH3:42])[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:44])[C:19]([CH3:21])([CH3:20])[CH3:22])=[C:13]([F:24])[CH:12]=3)[O:43][C:5]=2[C:4]([F:36])=[C:3]([CH3:37])[C:2]=1[F:1])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 19434955HCID 19434955, compound

Product 1

HCID 19434826HCID 19434826, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.02 g (1.89 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-(3-methanesulfonyloxypropylamino)-7-methyl-4H-1-benzopyran-4-one obtained in Example 116 (2) was dissolved in 30 mL of dimethylformamide, 2.0 mL (18.9 mmol) of diethylamine was added and the mixture was stirred at 80° C. for 15 hours. Water and a 1N aqueous solution of sodium hydroxide were 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 860 mg of 5-(3-diethylaminopropylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-one (yield: 88%).

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-21f8f39621f84886a4b49e6850d343e3
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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