HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrogen chloride-ethyl acetate → N-{3-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrogen chloride-ethyl acetate | HCID 21866389 | — |
| Reactant | Tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate | HCID 57387816 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | N-{3-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide | HCID 57385788 | 82.2% |
Reaction Steps
A mixture of tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate (2.37 g, 4.62 mmol), 4N hydrochloric acid-ethyl acetate solution (50 mL) and methanol (50 mL) was stirred at room temperature for 6 hr. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate alone→ethyl acetate/methanol=4:1) to give the title compound (1.57 g, 82%) as a green solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08034812B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-b64816825e004f90a459316ed4787c94 |
| Source note | uspto-grants-2011_10 |