Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Trimethylsilyldiazomethane | HCID 167693 | — |
| Reactant | HCID 59351688 | HCID 59351688 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 59351602 | HCID 59351602 | 62% |
Reaction Steps
To a mixture of 4′-{[2-ethyl-4-hydroxy-6-oxo-5-(2-phenylethyl)thieno[2,3-b]pyridin-7(6H)-yl]methyl}biphenyl-2-carbonitrile (0.5 g), diisopropylethylamine (0.72 mL), methanol (2 mL) and acetonitrile (18 mL) was added trimethylsilyldiazomethane (2M hexane solution, 0.72 mL), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with water and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.28 g, 62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08501750B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-81199476431b46c893d4eda3449ae8e1 |
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| Source note | uspto-grants-2013_08 |
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