Hydrochloric Acid → 5-chloro-4-[(3'-cyano-3-pyridazin-4-ylbiphenyl-4-yl)oxy]-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1619619Notes

Reaction equation

HRID 1619619 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][CH:39]=[C:38]([C:42]#[N:43])[CH:37]=3)=[CH:32][C:31]=2[C:44]2[CH:49]=[CH:48][N:47]=[N:46][CH:45]=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>CO.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][CH:39]=[C:38]([C:42]#[N:43])[CH:37]=3)=[CH:32][C:31]=2[C:44]2[CH:49]=[CH:48][N:47]=[N:46][CH:45]=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:9])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58042343HCID 58042343, compound

Product 1

HCID 566019855-chloro-4-[(3'-cyano-3-pyridazin-4-ylbiphenyl-4-yl)oxy]-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamideYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Chloro-4-(3′-cyano-3-(pyridazin-4-yl)biphenyl-4-yloxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 118, 550 mg, 0.77 mmol) was dissolved in methanol (2 mL) and a 4M solution of hydrogen chloride in 1,4-dioxane (10 mL) was added. The reaction mixture was stirred at room temperature for 18 hours and then concentrated in vacuo. The residue was co-evaporated with methanol and then purified by reverse phase chromatography (acetonitrile/water both with 0.1% formic acid) to give the title compound (303 mg, 70%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase chromatography (acetonitrile/water both with 0.1% formic acid)

Sources & evidence

ORD record
ord-51e57fb6c2dc4ebabec886d5eca826e3
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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