Potassium Carbonate → 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{2-pyridazin-4-yl-4-[2-(trifluoromethyl)pyridin-4-yl]phenoxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1619687Notes

Reaction equation

HRID 1619687 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH:10]=[CH:9][C:8]=2[OH:23])=[CH:3][N:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[C:32](F)=[CH:33][C:34]([F:57])=[C:35]([S:37]([N:40]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=2[O:55][CH3:56])[C:41]2[S:42][CH:43]=[N:44][N:45]=2)(=[O:39])=[O:38])[CH:36]=1>CS(C)=O>[Cl:30][C:31]1[C:32]([O:23][C:8]2[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=3)=[CH:12][C:7]=2[C:4]2[CH:5]=[CH:6][N:1]=[N:2][CH:3]=2)=[CH:33][C:34]([F:57])=[C:35]([S:37]([N:40]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=2[O:55][CH3:56])[C:41]2[S:42][CH:43]=[N:44][N:45]=2)(=[O:38])=[O:39])[CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 136200890HCID 136200890, compound

Product 1

HCID 580423345-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{2-pyridazin-4-yl-4-[2-(trifluoromethyl)pyridin-4-yl]phenoxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(Pyridazin-4-yl)-4-(2-(trifluoromethyl)pyridine-4-yl)phenol (Preparation 79, 0.105 mg, 0.33 mmol) was dissolved in DMSO (3 mL) and potassium carbonate (91 mg, 0.66 mmol) was added followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzensulfonamide (Preparation 16, 153 mg, 0.33 mmol). The mixture was stirred at room temperature for 3 hours and then partitioned between ethyl acetate (40 mL) and 1M aqueous sodium hydroxide solution (10 mL). The organic layer was separated and dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (207 mg, 81%) as a beige solid.

Workup

  1. custompartitioned between ethyl acetate (40 mL) and 1M aqueous sodium hydroxide solution (10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a267b9ea24d142beadf8aeb87d95e5c6
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

Loading…