HCID 10366027, compound → HCID 22041464, compound

HRID 1790235Notes

Reaction equation

HRID 1790235 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:16]=3[C:15]=2[CH3:24])(=[O:13])=[O:12])=[C:6]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:5]=1)(=[O:3])[CH3:2].[Br-:29].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:29][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:16]=3[C:15]=2[CH3:24])(=[O:12])=[O:13])=[C:6]([S:25]([CH3:28])(=[O:26])=[O:27])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 10366027HCID 10366027, compoundHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 22041464HCID 22041464, compoundYield 137.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into 4.0 mL of chloroform was dissolved 200 mg of Compound 19, and 194 mg of benzyltrimethylammonium tribromide was added, followed by 1 hour of stirring at room temperature. The reaction was terminated by adding water to the reaction solution and then the solvent was once removed by evaporation. The residue was adjusted to pH 2 to 3 by adding 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was washed with methanol to obtain 201 mg of N-(4-bromoacetyl-2-methanesulfonylphenyl)-5-fluoro-3-methylbenzo[b]thiophene-2-sulfonamide as a colorless solid. The thus obtained N-(4-bromoacetyl-2-methanesulfonylphenyl)-5-fluoro-3-methylbenzo[b]thiophene-2-sulfonamide (150 mg) was dissolved into a mixed solution of 1.5 mL of dioxane and 1.5 mL of ethanol, and 53 mg of sodium hydrogen carbonate and 26 mg of thioacetamide were successively added, followed by 2 hours of stirring under heating and refluxing. The reaction was terminated by adding water to the reaction solution and then the solvent was removed by evaporation under reduced pressure. The residue was adjusted to pH 2 to 3 by adding 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain 61 mg of the title compound as light yellow powder.

Workup

  1. additionwas added
  2. customThe reaction was terminated
  3. additionby adding water to the reaction solution
  4. customthe solvent was once removed by evaporation
  5. additionby adding 1 mol/L hydrochloric acid
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed by evaporation under reduced pressure
  10. washthe resulting residue was washed with methanol

Sources & evidence

ORD record
ord-4e4aa71acf48406f8e6045f64380a89b
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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