Trifluoroacetic acid → 3-{1-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide

HRID 1928249Notes

Reaction equation

HRID 1928249 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:16]=[CH:17][N:18]([C:20]3[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([CH3:34])[CH:28]=4)[N:21]=3)[CH:19]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:22]2[CH:23]=[C:24]([CH3:26])[N:25]=[C:20]([N:18]3[CH:19]=[C:15]([C:11]4[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=4)[N:16]=[CH:17]3)[N:21]=2)=[CH:28][C:29]=1[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57468996N-tert-Butyl-3-{1-[6-(4-chloro-3-methyl-phenyl)-4-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide

Product 1

HCID 574689953-{1-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of N-tert-butyl-3-{1-[6-(4-chloro-3-methyl-phenyl)-4-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide (0.53 g) in dichloromethane (5 ml) was added TFA (5 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness and saturated NaHCO3 solution (10 ml), diethylether 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 and dried. Further purification by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (THF/heptane) yielded the title compound as a white solid (0.3 g, 68%). MS (ISP) 440.1 [(M+H)+]; mp 219° C. (dec.).

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (10 ml), diethylether and heptane
  3. additionwere added
  4. stirringThe mixture was stirred at room temperature for 1 h
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water and heptane
  7. customdried
  8. customFurther purification by flash chromatography
  9. customon silica gel (ethyl acetate/heptane) and crystallization (THF/heptane)

Sources & evidence

ORD record
ord-4a50699c50c84fc884faafc88bdfc208
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

Loading…