Tert-butyl 4-{4-[4-(2-chloro-4-{[(2,4-dimethoxybenzyl)(pyrimidin-2-yl)amino]sulfonyl}-5-fluorophenoxy)-4'-(trifluoromethyl)biphenyl-3-yl]pyridin-2-yl}piperazine-1-carboxylate → 5-chloro-2-fluoro-4-{[3-(2-piperazin-1-ylpyridin-4-yl)-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamide

HRID 1619620Notes

Reaction equation

HRID 1619620 reaction equation
[Cl:1][C:2]1[CH:43]=[C:42]([S:44](=[O:64])(=[O:63])[N:45](CC2C=CC(OC)=CC=2OC)[C:46]2[N:51]=[CH:50][CH:49]=[CH:48][N:47]=2)[C:41]([F:65])=[CH:40][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][C:6]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([N:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)[CH:22]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[C:3]([O:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=3)=[CH:7][C:6]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([N:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)[CH:22]=2)=[CH:40][C:41]([F:65])=[C:42]([S:44]([NH:45][C:46]2[N:51]=[CH:50][CH:49]=[CH:48][N:47]=2)(=[O:63])=[O:64])[CH:43]=1

Participants

4

Reactant 1

HCID 58042255Tert-butyl 4-{4-[4-(2-chloro-4-{[(2,4-dimethoxybenzyl)(pyrimidin-2-yl)amino]sulfonyl}-5-fluorophenoxy)-4'-(trifluoromethyl)biphenyl-3-yl]pyridin-2-yl}piperazine-1-carboxylate

Product 1

HCID 566019865-chloro-2-fluoro-4-{[3-(2-piperazin-1-ylpyridin-4-yl)-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamideYield 11.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(4-(4-(2-chloro-4-(N-(2,4-dimethoxybenzyl)-N-(pyrimidin-2-yl)sulfamoyl)-5-fluorophenoxy)-4′-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate (Preparation 122, 360 mg, 0.385 mmol) was dissolved in a 4M solution of hydrogen chloride in 1,4-dioxane (5 mL). The reaction mixture was stirred at room temperature for 20 hours and then concentrated in vacuo. The residue was purified by reverse phase chromatography (acetonitrile/water both with 0.1% formic acid) to give the title compound (30 mg, 11%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-8b6cf7ce27ad40b3b92c0eb90e736cd0
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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