Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 57583914 | HCID 57583914 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57584174 | HCID 57584174 | — |
Reaction Steps
With cooling with ice, sodium hydride (60% oil suspension, 50 mg) was added to an N,N-dimethylformamide (10 ml) solution of methyl 4-{2-oxo-1-[2-(3-oxopiperazin-1-yl)ethyl]-1,2-dihydropyridin-3-yl}benzoate (380 mg), followed by stirring for 5 minutes, and then methyl iodide (70 μl) was added. With cooling with ice, the reaction mixture was stirred for 1.5 hours. Water with ice (20 ml) and aqueous saturated sodium hydrogencarbonate solution (10 ml) were added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain methyl 4-{1-[2-(4-methyl-3-oxopiperazin-1-yl)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoate (350 mg) as a pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08022208B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-93b29bdadd9e4d65b9a377633ecf7a44 |
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| Source note | uspto-grants-2011_09 |
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