Trifluoroacetic acid → HCID 23114773, compound

HRID 2080385Notes

Reaction equation

HRID 2080385 reaction equation
FC(F)(F)C(O)=O.C(OC(O[CH:16]([C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[F:34])[C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]=1)=O)(C)(C)C.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([SH:42])=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([S:42][CH:16]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[F:34])[C:17]2[N:21]([CH3:22])[C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:18]=2)=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 23114696HCID 23114696, compound

Product 1

HCID 23114773HCID 23114773, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (2.0 ml) was added to the 2-[(t-butoxycarbonyloxy)-(2,5-difluorophenyl)methyl]-1-methyl-1H-benzimidazole (204 mg, 0.545 mmol) obtained in Referential Example 13. The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. Dioxane was added to the residue, followed by further concentration under reduced pressure. The residue was dissolved in thionyl chloride (1.0 ml). One drop of dimethylformamide was added to the resulting solution. The resulting mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure. Dioxane was added to the residue and the resulting mixture was concentrated further under reduced pressure. The residue was dissolved in dimethylformamide (5.0 ml). After addition of 4-chlorobenzenethiol (118 mg, 0.82 mmol) and potassium carbonate (451 mg, 3.27 mmol), the resulting mixture was stirred at 50° C. for 2 hours. The reaction mixture was then allowed to stand at room temperature and ethyl acetate (60 ml) was added thereto. The resulting mixture was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 5:1) to give the title compound (195 mg, 89%) as a colorless oil.

Workup

  1. customobtained in Referential Example 13
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionDioxane was added to the residue
  4. concentrationfollowed by further concentration under reduced pressure
  5. dissolutionThe residue was dissolved in thionyl chloride (1.0 ml)
  6. additionOne drop of dimethylformamide was added to the resulting solution
  7. stirringThe resulting mixture was stirred for 16 hours at room temperature
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. additionDioxane was added to the residue
  10. concentrationthe resulting mixture was concentrated further under reduced pressure
  11. dissolutionThe residue was dissolved in dimethylformamide (5.0 ml)
  12. stirringthe resulting mixture was stirred at 50° C. for 2 hours
  13. customto stand at room temperature
  14. washThe resulting mixture was washed with water and brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue thus obtained
  18. customwas purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-2cda4a14e62f483e8e324dbb29c296e6
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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