Trifluoroacetic acid → 5-{3-[4-Methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide

HRID 1989742Notes

Reaction equation

HRID 1989742 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]([CH3:26])[CH:23]=[C:22]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[C:29]([CH3:37])[CH:28]=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>[CH3:26][C:24]1[CH:23]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[C:29]([CH3:37])[CH:28]=2)[N:21]=[C:20]([C:16]2[CH:15]=[C:14]([C:11]3[S:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:13][CH:12]=3)[CH:19]=[CH:18][CH:17]=2)[N:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57469109N-tert-Butyl-5-{3-[4-methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide

Product 1

HCID 574691085-{3-[4-Methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amideYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of N-tert-butyl-5-{3-[4-methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide (0.15 g) in dichloromethane (3 ml) was added TFA (3 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 crystallization (ethyl acetate/heptane) yielded the title compound as a light brown solid (0.064 g, 25%). MS (ISP) 490.1 [(M+H)+]; mp 242° 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
  9. customby crystallization (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-5cfbba636dcd4c72bdd9ba697e355b31
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

Loading…