Trifluoroacetic acid → 4-Methyl-2-{1-[6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid amide

HRID 1989620Notes

Reaction equation

HRID 1989620 reaction equation
C([NH:5][S:6]([C:9]1[S:13][C:12]([C:14]2[N:15]=[CH:16][N:17]([C:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[CH:22]=[C:21]([C:35]([F:38])([F:37])[F:36])[N:20]=3)[CH:18]=2)=[N:11][C:10]=1[CH3:39])(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:39][C:10]1[N:11]=[C:12]([C:14]2[N:15]=[CH:16][N:17]([C:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[CH:22]=[C:21]([C:35]([F:37])([F:36])[F:38])[N:20]=3)[CH:18]=2)[S:13][C:9]=1[S:6]([NH2:5])(=[O:8])=[O:7]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 247608934-Methyl-2-{1-[6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid tert-butylamide

Product 1

HCID 247609724-Methyl-2-{1-[6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid amideYield 51.7%

Conditions

Temperature
23 °C

Procedure

To 4-methyl-2-{1-[6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid tert-butylamide (example 300) (0.150 g, 0.254 mmol) was added TFA (5 mL) and the reaction mixture was stirred at 23° C. for 16 h. The mixture was evaporated to dryness and partitioned between TBME 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 (0.070 g, 51%). MS (ISP) 534.2 [(M+H)+]; mp 170° C. (dec.).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between TBME 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-d8f85e9ed4f344768156d787f0a4908a
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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