Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 57515883 | HCID 57515883 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | HCID 25168279 | HCID 25168279 | — |
Reaction Steps
To a microwave vial is added N-((1S)-1-((1R)-2-(((4S)-8-bromo-6-(2,2-dimethylpropyl)-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-4-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)-2-methoxyacetamide (100 mg, 191 μmol), cesium carbonate (311 mg, 955 μmol), 1H-imidazole (65 mg, 955 μmol), and copper(I) iodide (36 mg, 191 μmol). The vial was purged with N2 5×, then 10:1 DMF/H2O (2 mL) and N1,N2-dimethylethane-1,2-diamine (21 μl, 191 μmol) were added. The vial was sealed and heated in a microwave at 185° C. for 30 min. The crude product was dissolved in DMF, filtered through an Acrodisc filter and purified by reverse phase HPLC to afford the title compound as a white amorphous solid. MS m/z=511.4 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08633315B2 |
|---|
| Source dataset | uspto-grants-2014_01 |
|---|
| ORD ID | ord-62bdfc63d6fb477a886a35e6d9bb9056 |
|---|
| Source note | uspto-grants-2014_01 |
|---|
