Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Chloromethyl)pyridinium chloride | HCID 74570 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 23062699 | HCID 23062699 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 10289015 | HCID 10289015 | 88.7% |
Reaction Steps
3-((Piperidin-4-yl)carbonylamino)-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (100 mg) obtained in Example 228 is suspended in N,N-dimethylacetamide (3 ml), and thereto are added 4-(chloromethyl)pyridine hydrochloride (45 mg), sodium carbonate (80 mg) and sodium iodide (41 mg), and the mixture is stirred at room temperature for 12 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with water and a saturated brine, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1, then 1/1) to give the title compound (109 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07531537B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-fe96bd092090448ebb05c54e67536104 |
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| Source note | uspto-grants-2009_05 |
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