Trifluoroacetic acid → HCID 57469130, compound

HRID 1928509Notes

Reaction equation

HRID 1928509 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:25]=[C:24]([CH:26]([F:28])[F:27])[CH:23]=[C:22]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=4)[N:21]=3)[CH:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:28][CH:26]([F:27])[C:24]1[CH:23]=[C:22]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:36])[F:38])=[CH:31][CH:30]=2)[N:21]=[C:20]([C:16]2[CH:15]=[C:14]([C:11]3[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=3)[CH:19]=[CH:18][CH:17]=2)[N:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57469131HCID 57469131, compound

Product 1

HCID 57469130HCID 57469130, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of N-tert-butyl-5-{3-[4-difluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide (0.4 g) in dichloromethane (7 ml) was added TFA (7 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness, poured into 2N Na2CO3 solution (20 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. Further purification by flash-chromatography on silica gel (ethyl acetate/hexane) and crystallization (dichloromethane) yielded the title compound as a white solid (0.064 g, 13%). MS (ISP) 512.3 [(M+H)+]; mp 240.5° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness
  3. additionpoured into 2N Na2CO3 solution (20 ml)
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined organic layers were washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customFurther purification by flash-chromatography
  9. customon silica gel (ethyl acetate/hexane) and crystallization (dichloromethane)

Sources & evidence

ORD record
ord-18ecb5430b9b4e15aef9b9d32dcf5ec4
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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