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

HRID 1928312Notes

Reaction equation

HRID 1928312 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]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=4)[N:20]=3)[CH:18]=2)=[N:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[F:28][C:25]([F:26])([F:27])[C:23]1[CH:22]=[C:21]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:38])[F:37])=[CH:33][CH:34]=2)[N:20]=[C:19]([N:17]2[CH:18]=[C:14]([C:12]3[S:13][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:10][N:11]=3)[N:15]=[CH:16]2)[CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 602094682-{1-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid tert-butylamide

Product 1

HCID 574690312-{1-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid amideYield 86%

Procedure

To 2-{1-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid tert-butylamide (example 281) (0.160 g, 0.28 mmol) was added TFA (5 mL) and the reaction mixture was allowed to stir at room temperature for 24 h. The mixture was evaporated to dryness and saturated NaHCO3 solution (5 mL), diethyl ether and heptane were added. The mixture was stirred at room temperature for 1 h, the precipitate was collected by filtration, washed with water and heptane/diethyl ether and dried to yield the title compound as an off-white solid (0.124 g, 86%). MS (ISP) 520.2 [(M+H)+]; mp>266° C.

Workup

  1. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (5 mL), diethyl ether and heptane
  2. additionwere added
  3. stirringThe mixture was stirred at room temperature for 1 h
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water and heptane/diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-8c0b0d9242334bf7ad920674c8c7b8fc
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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