Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1309377-79-4 | HCID 71757168 | — |
| Reactant | 4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate | HCID 89442764 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | Trifluoroacetic acid | HCID 6422 | 250.7% |
| Product | 4-(4-(1-(2-(azetidin-1-yl)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine | HCID 74221573 | — |
Reaction Steps
A reaction mixture of 4-chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine (30.0 mg; 0.17 mmol; 1.0 eq.), 4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate (109.2 mg; 0.17 mmol; 1.0 eq.) and cesium carbonate (227.8 mg; 0.7 mmol; 4.0 eq.) in 1 ml of DMSO was stirred at 120° C. for 48 hrs. The reaction mixture was purified by pre-HPLC to afford the title compound as TFA salt (48.6 mg, 43% yield); LC-MS (M+H=532, obsd.=532);
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09315517B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-e47ef14d0dad4bb1a8c7ac6dca292ef2 |
|---|
| Source note | uspto-grants-2016_04 |
|---|
