HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Diaminocyclohexane, trans- → 1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Diaminocyclohexane, trans- | HCID 43806 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 5-Bromo-2,2-difluoro-1,3-benzodioxole | HCID 2736271 | — |
| Reactant | 1-(4-Methylpyridin-3-yl)imidazolidin-2-one | HCID 59636170 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one | HCID 49872148 | 92.2% |
Reaction Steps
Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.84650 mmol) was reacted with 5-bromo-2,2-difluoro-benzo[1,3]dioxole (200.6 mg, 0.84650 mmol), 1,4-dioxane (50 mL), copper iodide (16 mg, 0.084650 mmol), trans-1,2-diamino cyclohexane (29 mg, 0.2539 mmol) and potassium phosphate (538 mg, 2.539 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 260 mg of the product (92% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | USRE045173E1 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-a13c01077c164d728795c5fbebbd9ddc |
| Source note | uspto-grants-2014_09 |