Trifluoroacetic acid → HCID 178460790, compound

HRID 914396Notes

Reaction equation

HRID 914396 reaction equation
C([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17](O)=O)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:32]=[C:31]([NH2:33])[NH:30][N:29]=2)=[CH:24][CH:23]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:32]=[C:31]([NH:33][CH2:17][CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:5])=[O:20])[S:12][CH:13]=3)[NH:30][N:29]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 59759443{2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acidHCID 178507284HCID 178507284, compound

Product 1

HCID 178460790HCID 178460790, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained using {2-[(2-tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid synthesized in Example 3 and 3-(4-chlorophenyl)-1H-pyrazole-5-amine as starting materials and by operations similar to those of Example 242-1 and Example 242-2 was treated with dichloromethane and trifluoroacetic acid, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution (The objective compound was extracted in the saturated aqueous sodium hydrogen carbonate solution layer). Aqueous 10% citric acid solution was added to the aqueous layer, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound.

Workup

  1. customThe compound obtained
  2. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  3. additionwas added
  4. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution (The objective compound
  5. extractionwas extracted in the saturated aqueous sodium hydrogen carbonate solution layer)
  6. additionAqueous 10% citric acid solution was added to the aqueous layer
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0a11d4c4ab5745bfb7e811b5b1fd0ca7
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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