Potassium Carbonate → 5-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamide

HRID 1619659Notes

Reaction equation

HRID 1619659 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:29])=[C:6]([S:8]([N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=2[O:27][CH3:28])[C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.[N:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:38]=[C:39]([C:44]3[CH:49]=[CH:48][C:47]([C:50]([F:53])([F:52])[F:51])=[CH:46][CH:45]=3)[CH:40]=[CH:41][C:42]=2[OH:43])=[CH:33][N:32]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[C:3]([O:43][C:42]2[CH:41]=[CH:40][C:39]([C:44]3[CH:45]=[CH:46][C:47]([C:50]([F:51])([F:52])[F:53])=[CH:48][CH:49]=3)=[CH:38][C:37]=2[C:34]2[CH:35]=[CH:36][N:31]=[N:32][CH:33]=2)=[CH:4][C:5]([F:29])=[C:6]([S:8]([N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=2[O:27][CH3:28])[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:17]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 580422645-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(pyrimidin-2-yl)benzenesulfonamideHCID 1362008883-Pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-ol

Product 1

HCID 580423475-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamideYield 101%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-pyrimidin-2-yl-benzenesulfonamide (Preparation 13, 216 mg, 0.47 mmol), 3-pyridazin-4-yl-4′-(trifluoromethyl)biphenyl-4-ol (Preparation 8, 150 mg, 0.47 mmol) and potassium carbonate (196 mg, 1.42 mmol) were stirred in dimethylsulfoxide (3 mL) at room temperature for 18 hours. A 1M aqueous solution of sodium hydroxide was added to the reaction mixture whereupon a precipitate was observed. The precipitate was collected by filtration and dissolved in ethyl acetate. The ethyl acetate was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as a solid (357 mg, 100%).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialThe ethyl acetate was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ff8ce492d38451cb7c4b8762da66d3b
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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