Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Cyclopentanone | HCID 8452 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 67011094 | HCID 67011094 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 24992520 | HCID 24992520 | — |
Reaction Steps
6-[6-(piperidin-4-yloxy)-pyridin-3-yl]-2H-pyridazin-3-one hydrochloride (407 mg, 1.18 mmol) in a mixture of DMF (5 mL), methanol (15 mL), and acetic acid (250 μL) was added cyclopentanone (314 μL, 3.54 mmol), followed by sodium cyanoborohydride (371 mg, 5.9 mmol). After stirring at 60° C. for 2 h, the reaction was concentrated, partitioned between dichloromethane/1N sodium carbonate, washed with water/brine, dried over sodium sulfate, and concentrated. The product was purified using prep TLC plates (9:1 dichloromethane:methanol) (25%); Mp 233-237° C.; MS m/z 341 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586588B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-aec7cd802bcd4df2afccfd0387fd6591 |
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| Source note | uspto-grants-2013_11 |
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