Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(2-Bromoethoxy)tetrahydro-2H-pyran | HCID 86621 | — |
| Reactant | HCID 117701579 | HCID 117701579 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 117701726 | HCID 117701726 | 74% |
Reaction Steps
To a solution of 7-hydroxy-3,8-dimethyl-2-[(2R)-pyrrolidin-2-yl]-4H-chromen-4-one hydrochloride (70 mg, 0.27 mmol) obtained in Example 2-3 and triethylamine (56 μL, 0.40 mmol) in dimethylformamide (1.5 mL), 2-(2-bromoethoxy)tetrahydro-2H-pyran (163 μL, 1.08 mmol) was added dropwise, and then the mixture was stirred at room temperature for 20 hours. Triethylamine (38 μL, 0.27 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran (41 μL, 0.27 mmol) were further added dropwise thereto, and then the mixture was stirred at room temperature for 27 hours. The reaction solution was concentrated, and then the obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→90/10) to obtain 77 mg of the title compound (yield: 74%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221811B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-22f6cc4c1f494deb84c4640deef23cfc |
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| Source note | uspto-grants-2015_12 |
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