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

HRID 1736196Notes

Reaction equation

HRID 1736196 reaction equation
[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7]I)(=[O:3])[CH3:2].Cl.[CH3:31][NH:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7][N:32]([CH3:33])[CH3:31])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 194348032-[4-[N-acetyl-N-(3-iodopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

Product 1

HCID 194349332-[4-[N-acetyl-N-(3-dimethylaminopropyl) amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-oneYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.16 g (13.9 mmol) of the above 2-[4-[N-acetyl-N-(3-iodopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 150 mL of dimethylformamide under argon atmosphere, 5.68 g (69.5 mmol) of dimethylamine hydrochloride and 9.61 g (69.5 mmol) of potassium carbonate were added and the mixture was stirred at room temperature for 14 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:methanol=20:1-6:1-chloroform:methanol:aqueous ammonia=9:1:1) to give 4.13 g of 2-[4-[N-acetyl-N-(3-dimethylaminopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one (yield: 69%).

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=20:1-6:1-chloroform:methanol:aqueous ammonia=9:1:1)

Sources & evidence

ORD record
ord-6deb141d443d4ef596ccd9e675624eb9
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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