Trifluoroacetic acid → 3-{1-[4-Difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide

HRID 906289Notes

Reaction equation

HRID 906289 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:16]=[CH:17][N:18]([C:20]3[N:25]=[C:24]([CH:26]([F:28])[F:27])[CH:23]=[C:22]([C:29]4[CH:30]=[N:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=4)[N:21]=3)[CH:19]=2)[CH:10]=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:30]=[N:31][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:34]=2)[N:21]=[C:20]([N:18]2[CH:19]=[C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=3)[N:16]=[CH:17]2)[N:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673932143-{1-[4-Difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonic acid tert-butylamide

Product 1

HCID 673933083-{1-[4-Difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamideYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 3-{1-[4-difluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonic acid tert-butylamide (0.06 g) in dichloromethane (2 ml) was added TFA (2 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 (25 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 column chromatography on silica gel (dichloromethane/MeOH/NH4OH 16:1:0.1) and crystallization (diethyl ether) yielded the title compound as a white solid (0.022 g, 4%). MS (ISP) 497.2 [(M+H)+]; mp 219.5° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness
  3. additionpoured into 2N Na2CO3 solution (25 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 column chromatography
  9. customon silica gel (dichloromethane/MeOH/NH4OH 16:1:0.1) and crystallization (diethyl ether)

Sources & evidence

ORD record
ord-9e542dab135943b59c9f6aa86c80ba7a
Source dataset
uspto-grants-2011_09
Patent number
US08012986B2

Reaction notes

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