5-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide → 5-Chloro-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1619589Notes

Reaction equation

HRID 1619589 reaction equation
[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=3)=[CH:32][C:31]=2[C:46]2[CH:51]=[CH:50][N:49]=[N:48][CH:47]=2)=[CH:4][C:5]([F:28])=[C:6]([S:8]([N:11](CC2C=CC(OC)=CC=2OC)[C:12]2[S:13][CH:14]=[N:15][N:16]=2)(=[O:10])=[O:9])[CH:7]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:38][CH:37]=3)=[CH:32][C:31]=2[C:46]2[CH:51]=[CH:50][N:49]=[N:48][CH:47]=2)=[CH:4][C:5]([F:28])=[C:6]([S:8]([NH:11][C:12]2[S:13][CH:14]=[N:15][N:16]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 1

HCID 671227215-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

Product 1

HCID 566007875-Chloro-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamideYield 26%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[3-pyridazin-4-yl-4′-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 24, 213 mg, 0.28 mmol) was dissolved a in 4M solution of hydrogen chloride in 1,4-dioxane (7 mL) and stirred at room temperature for 3 hours. A precipitate formed which was collected by filtration and purified by reverse phase preparative HPLC (Trilution method) to afford the title compound as a solid (44 mg, 26%).

Workup

  1. customA precipitate formed which
  2. filtrationwas collected by filtration
  3. custompurified by reverse phase preparative HPLC (Trilution method)

Sources & evidence

ORD record
ord-52508142e7c44f13af98cf998506be70
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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