Water → HCID 19434838, compound

HRID 1736117Notes

Reaction equation

HRID 1736117 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])(=[O:3])[CH3:2].[CH3:26][S:27][CH2:28][CH2:29]Cl.CC(C)([O-])C.[K+].O>CN(C)C=O>[C:1]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])[CH2:29][CH2:28][S:27][CH3:26])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 109652-Chloroethyl methyl sulfide2×HCID 194349072-(4-Acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-4H-1-benzopyran-4-oneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 19434838HCID 19434838, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g (2.87 mmol) of Compound 27 obtained in Example 27 was dissolved in 30 ml of dimethylformamide under argon atmosphere, 1.43 ml of chloroethyl methyl sulfide and 354 mg of potassium tert-butoxide were added under ice-cooling and the mixture was stirred at 50° to 60 ° C. for 1 hour. Additional 0.29 ml of chloroethyl methyl sulfide and 322 mg of potassium tert-butoxide were added and the mixture was stirred at the same temperature for 17 hours. The reaction solution was cooled on ice, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 380 mg (32%) of 2-[4-[N-acetyl-N-(2-methylthioethyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 17 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-0dbad8bc26c741dc86343c87841add57
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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