HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → 1-Methyl-4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)methyl)piperidin-4-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 4-(Aminomethyl)-1-methylpiperidin-4-ol | HCID 6484262 | — |
| Reactant | 6-Chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine | HCID 59379861 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 1-Methyl-4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)methyl)piperidin-4-ol | HCID 66598069 | 10.9% |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
CsF (50 mg, 0.33 mmol) was added to the mixture of 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (150 mg, 0.48 mmol) and 4-(aminomethyl)-1-methylpiperidin-4-ol (150 mg, 1.04 mmol) in DMSO (1.5 mL). The mixture was heated to 120° C. over night and partitioned with EtOAc (10 mL) and water (10 mL). The organic layer was washed with brine (8 mL×3), dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by pre-HPLC to give the product 1-methyl-4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)methyl)piperidin-4-ol (22 mg, 10%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09416132B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-86f3a79c95464a90988948515f51df22 |
| Source note | uspto-grants-2016_08 |