Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone | HCID 59326874 | — |
| Reactant | HCID 59351368 | HCID 59351368 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59351300 | HCID 59351300 | — |
Reaction Steps
The mixture of (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (112 mg, 0.468 mmol), methyl 4-(3-fluoropyrazin-2-yl)piperidine-1-carboxylate (56 mg, 0.23 mmol), and cesium carbonate (153 mg, 0.468 mmol) in DMSO (0.8 mL) was heated at 80° C. for 20 h. The reaction mixture was partitioned between EtOAc and brine. The aqueous layer was back extracted with EtOAc (3×) and the combined organic layer was dried (Na2SO4) and concentrated. The crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 100% EtOAc in hexane, to provide methyl 4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate as white solid. MS (ESI, pos. ion) m/z: 458.1 (M+1). IC50 (uM) +++++.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08329700B2 |
|---|
| Source dataset | uspto-grants-2012_12 |
|---|
| ORD ID | ord-9c883f21aaa3441ba40ec6bcb4a1e7bb |
|---|
| Source note | uspto-grants-2012_12 |
|---|