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

HRID 1928192Notes

Reaction equation

HRID 1928192 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[C:19]([C:21]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH3:34])[N:22]=3)[CH:18]=[CH:17][N:16]=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:25]2[CH:24]=[C:23]([CH3:34])[N:22]=[C:21]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]([C:11]4[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=4)[CH:20]=3)[N:26]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 602094353-{4-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid tert-butylamide

Product 1

HCID 574689363-{4-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 3-{4-[4-(4-chloro-phenyl)-6-methyl-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid tert-butylamide (0.47 g) in dichloromethane (6 mL) was added TFA (6 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 (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 and dried to yield the title compound as a white solid (0.2, 46%). MS (ISP) 437.1 [(M+H)+]; mp 224° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (5 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-555296a04e87428e857ee873a59f1cf0
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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