HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,10-Phenanthroline → HCID 178454064, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,10-Phenanthroline | HCID 1318 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | cis-4-(tert-Butoxycarbonylamino)cyclohexanol | HCID 1514287 | — |
| Reactant | 6-Iodo-3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]triazolo[4,3-a]pyridine | HCID 66977545 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178454064 | HCID 178454064 | 73.3% |
Reaction Steps
A mixture of Example 1 step b (234 mg, 0.52 mmol), copper (I) iodide (9 mg, 0.052 mmol), 1,10-phenanthroline (19 mg, 0.104 mmol), cesium carbonate (335 mg, 1.04 mmol) and trans-4-boc-aminocyclohexanol (560 mg, 2.6 mmol) in toluene (3 mL) was heated at 110° C. for 72 h under an argon atmosphere. The suspension was cooled to RT, diluted with EtOAc (10 mL) and filtered through HiFlo. The filtrate was concentrated in vacuo and the residue purified by reverse phase preparative HPLC (Method 3) to afford the title compound (205 mg, 39%) as an off-white solid. LCMS (Method 2): Rt 2.53 min, m/z 538 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08557797B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-c00f5bfe70e341b997c8ca8b566c3676 |
| Source note | uspto-grants-2013_10 |