Trifluoroacetic acid → 3'-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid amide

HRID 1928404Notes

Reaction equation

HRID 1928404 reaction equation
C([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([CH3:34])[CH:28]=4)[CH:24]=[C:23]([CH3:35])[N:22]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=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:25]2[CH:24]=[C:23]([CH3:35])[N:22]=[C:21]([C:17]3[CH:16]=[C:15]([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:10]=4)[CH:20]=[CH:19][CH:18]=3)[N:26]=2)=[CH:28][C:29]=1[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 602094753'-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide

Product 1

HCID 574690533'-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid amideYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 3′-[4-(4-chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide (0.45 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), 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. The crude product was further purified by flash chromatography on silica gel (ethylacetate/heptane) and crystallization (dichloromethane/MeOH/hexane) to yield the title compound as a white solid (0.29 g, 65%). MS (ISP) 450.1 [(M+H)+]; mp 201° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (5 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. customThe crude product was further purified by flash chromatography on silica gel (ethylacetate/heptane) and crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-68b5d78b5db544768b3c2f2ac946c831
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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