Hydrochloric Acid → 5-Chloro-2-fluoro-4-({3-[2-(piperazin-1-yl)pyridin-4-yl]-4'-(trifluoromethyl)biphenyl-4-yl}oxy)-N-(pyrimidin-4-yl)benzenesulfonamide hydrochloride salt

HRID 1619615Notes

Reaction equation

HRID 1619615 reaction equation
Cl.[Cl:2][C:3]1[CH:44]=[C:43]([S:45](=[O:65])(=[O:64])[N:46](CC2C=CC(OC)=CC=2OC)[C:47]2[CH:52]=[CH:51][N:50]=[CH:49][N:48]=2)[C:42]([F:66])=[CH:41][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[CH:8][C:7]=1[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)[CH:23]=1>O1CCOCC1.CO>[ClH:2].[Cl:2][C:3]1[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=3)=[CH:8][C:7]=2[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([N:28]3[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]3)[CH:23]=2)=[CH:41][C:42]([F:66])=[C:43]([S:45]([NH:46][C:47]2[CH:52]=[CH:51][N:50]=[CH:49][N:48]=2)(=[O:65])=[O:64])[CH:44]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58042259Tert-butyl 4-{4-[4-(2-chloro-4-{[(2,4-dimethoxybenzyl)(pyrimidin-4-yl)amino]sulfonyl}-5-fluorophenoxy)-4'-(trifluoromethyl)biphenyl-3-yl]pyridin-2-yl}piperazine-1-carboxylate

Product 1

HCID 566017845-Chloro-2-fluoro-4-({3-[2-(piperazin-1-yl)pyridin-4-yl]-4'-(trifluoromethyl)biphenyl-4-yl}oxy)-N-(pyrimidin-4-yl)benzenesulfonamide hydrochloride saltYield 163.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4M solution of hydrogen chloride in 1,4-dioxane (10 mL) was added to a solution of tert-butyl 4-(4-(4-(2-chloro-4-(N-(2,4-dimethoxybenzyl)-N-(pyrimidin-4-yl)sulfamoyl)-5-fluorophenoxy)-4′-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate (Preparation 109, 310 mg, 0.332 mmol) in methanol (2 mL). The reaction mixture was stirred at room temperature for 3 hours and then concentrated in vacuo. The residue was purified by reverse phase chromatography (acetonitrile/water with 0.1% formic acid) to afford the title compound (196 mg, 82%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by reverse phase chromatography (acetonitrile/water with 0.1% formic acid)

Sources & evidence

ORD record
ord-829a5e80c883412bb0460d888b363fe7
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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