Trifluoroacetic acid → 3-{4-[4-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidin-2-yl}-benzenesulfonamide

HRID 1928336Notes

Reaction equation

HRID 1928336 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)[N:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:27][C:25]1[CH:24]=[C:23]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][CH:29]=2)[N:22]=[C:21]([C:19]2[CH:18]=[CH:17][N:16]=[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:20]=2)[CH:26]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57469042HCID 57469042, compound

Product 1

HCID 574690413-{4-[4-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidin-2-yl}-benzenesulfonamideYield 262.9%

Conditions

Temperature
50 °C

Procedure

To the above prepared N-tert-butyl-3-{4-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidin-2-yl}-benzenesulfonamide (0.110 g, 0.19 mmol) was added TFA (6 mL) and the reaction mixture was stirred at 50° C. for 2 h. The mixture was evaporated to dryness and partitioned between EtOAc and saturated NaHCO3 solution, the organic layer was dried over Na2SO4. Removal of the solvent in vacuum left a crude product which was triturated with diethyl ether to give the title compound as a white solid (0.235 g, 100%). MS (ISP) 471.2 [(M+H)+]; mp>250° C.

Workup

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a crude product which
  6. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-46e663c6bf7c455a969ea6b5b033b3dc
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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