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

HRID 1928168Notes

Reaction equation

HRID 1928168 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])=[CH:29][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:29]=[CH:28][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:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57468915N-tert-Butyl-3-{1-[6-(4-chloro-phenyl)-4-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide

Product 1

HCID 574689143-{1-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamideYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of N-tert-butyl-3-{1-[6-(4-chloro-phenyl)-4-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide (0.103 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 saturated NaHCO3 solution (3 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 and dried to yield the title compound as a white solid (0.046 g, 11%). MS (ISP) 426.0 [(M+H)+]; mp 275° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (3 mL), diethyl ether 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

Sources & evidence

ORD record
ord-e3a4aa0ed85543f3a131a08b3ad53f03
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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