HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → 2-(3-(4-(7-(1-isopropyl-1-H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2,2,2-Trifluoroethyl trifluoromethanesulfonate | HCID 80366 | — |
| Reactant | 2-(3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride | HCID 67456943 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(3-(4-(7-(1-isopropyl-1-H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrile | HCID 68230773 | 47% |
Reaction Steps
To a flask charged with 2-(3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (0.050 g, 0.10 mmol) was added 1 mL of acetonitrile, potassium carbonate (0.10 g, 0.75 mmol), and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.040 g, 0.17 mmol) at ambient temperature with stirring. The reaction flask was then sealed and allowed to proceed at ambient temperature over the weekend. The reaction was diluted with DCM and the suspension was loaded directly onto a silica gel column pre-wetted and eluted with 75% ethyl acetate in Hexanes with 1% ammonium hydroxide to afford the title compound (0.022 g, 0.047 mmol, 47% yield). MS (apci) m/z=470.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08962596B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-ccd7bc7b820640f4929930832e8b2363 |
| Source note | uspto-grants-2015_02 |