Water → 2-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-6,8-difluoro-7-methyl-5-(1-pentylamino)-4H-1-benzopyran-4-one

HRID 1736173Notes

Reaction equation

HRID 1736173 reaction equation
[C:1]([N:4]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[C:24]([F:25])=[C:23]([CH3:26])[C:22]([F:27])=[C:21]([NH2:28])[C:17]=3[C:18](=[O:20])[CH:19]=2)=[CH:10][C:9]=1[F:29])[CH2:5][CH2:6][CH3:7])(=[O:3])[CH3:2].[H-].[Na+].I[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].O>CN(C)C=O>[C:1]([N:4]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[C:24]([F:25])=[C:23]([CH3:26])[C:22]([F:27])=[C:21]([NH:28][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:17]=3[C:18](=[O:20])[CH:19]=2)=[CH:10][C:9]=1[F:29])[CH2:5][CH2:6][CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 123351-IodopentaneHCID 24758Sodium hydrideHCID 194348902-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one

Product 1

HCID 194350112-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-6,8-difluoro-7-methyl-5-(1-pentylamino)-4H-1-benzopyran-4-oneYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

299 mg (0.740mmol) of the above 2-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one was dissolved in 10 mL of dimethylformamide under argon atmosphere, 60 mg (1.5 mmol) of sodium hydride (60% oil dispersion) and 0.98 mL (7.4 mmol) of 1-iodopentane were added under ice-cooling and the mixture was stirred at room temperature for 6 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) to give 91.2 mg of 2-[4-[N-acetyl-N-(1-propyl)amino]-3-fluorophenyl]-6,8-difluoro-7-methyl-5-(1-pentylamino)-4H-1-benzopyran-4-one (yield: 26%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted once 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)

Sources & evidence

ORD record
ord-7e767acef2a84e2ca438ed2692e3b5fa
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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