Hydrochloric Acid → 5-Chloro-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamide

HRID 1619586Notes

Reaction equation

HRID 1619586 reaction equation
[Cl:1][C:2]1[C:3]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)=[CH:33][C:32]=2[C:47]2[CH:52]=[CH:51][N:50]=[N:49][CH:48]=2)=[CH:4][C:5]([F:29])=[C:6]([S:8]([N:11](CC2C=CC(OC)=CC=2OC)[C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:45])([F:44])[F:46])=[CH:41][CH:42]=3)=[CH:33][C:32]=2[C:47]2[CH:52]=[CH:51][N:50]=[N:49][CH:48]=2)=[CH:4][C:5]([F:29])=[C:6]([S:8]([NH:11][C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:17]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 580423475-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamide

Product 1

HCID 566005805-Chloro-2-fluoro-4-{[3-pyridazin-4-yl-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamideYield 42.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[3-pyridazin-4-yl-4′-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamide (Preparation 48) 356 mg, 0.47 mmol) was dissolved in 1,4-dioxane (1.5 mL) and a 4M solution of hydrogen chloride in 1,4-dioxane (2.4 mL) added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the resulting residue purified by reverse phase preparative HPLC (Trilution method) to afford the title compound as a white solid (120 mg, 42%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue purified by reverse phase preparative HPLC (Trilution method)

Sources & evidence

ORD record
ord-62e5b22bafce42668224b7bb4ebd4aa4
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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