HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 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 | HCID 58042255 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-chloro-2-fluoro-4-{[3-(2-piperazin-1-ylpyridin-4-yl)-4'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-pyrimidin-2-ylbenzenesulfonamide | HCID 56601986 | 11.4% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08772293B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-8b6cf7ce27ad40b3b92c0eb90e736cd0 |
| Source note | uspto-grants-2014_07 |