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

HRID 1989458Notes

Reaction equation

HRID 1989458 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]3N=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH:22]=[C:21]([C:32]([F:35])([F:34])[F:33])[N:20]=3)[CH:18]=2)=[N:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.[C:36](O)(C(F)(F)F)=O>ClCCl>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[CH:22]=[C:21]([C:32]([F:34])([F:33])[F:35])[N:20]=[C:19]([N:17]3[CH:18]=[C:14]([C:12]4[S:13][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:10][N:11]=4)[N:15]=[CH:16]3)[CH:36]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57468927N-tert-butyl-2-{1-[4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonamide

Product 1

HCID 686953552-{1-[4-(4-Chloro-phenyl)-6-trifluoromethyl-pyridin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonic acid amideYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of N-tert-butyl-2-{1-[4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonamide (0.088 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 and purified by flash-chromatography on silica gel (ethyl acetate/hexane) and crystallization (THF/hexane) to yielded the title compound as a light brown solid (0.03 g, 14%). MS (ISN) 485.2 [(M−H)−]; mp 263° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness
  3. custompurified by flash-chromatography on silica gel (ethyl acetate/hexane) and crystallization (THF/hexane)

Sources & evidence

ORD record
ord-7da7427a843a4521b3e585d29288543c
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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