Trifluoroacetic acid → HCID 178506540, compound

HRID 910243Notes

Reaction equation

HRID 910243 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:20]=[CH:19][N:18](C(OC(C)(C)C)=O)[N:17]=4)=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:28]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([C:16]4[CH:20]=[CH:19][NH:18][N:17]=4)=[CH:14][CH:15]=3)=[N:7][C:6]=2[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67405262HCID 67405262, compound

Product 1

HCID 178506540HCID 178506540, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Subsequently, tert-butyl 3-[4-(5-iodo-1,3-benzoxazol-2-yl)phenyl]-1H-1-pyrazolecarboxylate (14.6 mg) was dissolved in chloroform (500 μL), and trifluoroacetic acid (231 μL) was added to the solution, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, followed by drying. The thus-obtained white solid was dissolved in chloroform, and the solution was washed sequentially with 1N aqueous sodium hydroxide, water, and saturated saline, followed by drying over magnesium sulfate. The solvent was evaporated under reduce pressure, and the solid was recovered through filtration by use of isopropyl ether, followed by drying under reduced pressure, to thereby yield the title compound (9.8 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customby drying
  3. dissolutionThe thus-obtained white solid was dissolved in chloroform
  4. washthe solution was washed sequentially with 1N aqueous sodium hydroxide, water, and saturated saline
  5. dry with materialby drying over magnesium sulfate
  6. customThe solvent was evaporated
  7. filtrationthe solid was recovered through filtration by use of isopropyl ether
  8. customby drying under reduced pressure

Sources & evidence

ORD record
ord-cb9f05a5b750475c8f67e37817362ea1
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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