Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | N-(3-chloropropyl)piperidine hydrochloride | HCID 79624 | — |
| Reactant | HCID 18467081 | HCID 18467081 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 70149984 | HCID 70149984 | 53.2% |
Reaction Steps
To a solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-(2,6-diisopropyl-4-hydroxyphenyl)urea(254 mg, 0.47 mmol) in DMF (7 ml) are added successively potassium carbonate (193 mg, 1.40 mmol), potassium iodide (39 mg, 0.23 mmol), 1-(3-chloropropyl)piperidine hydrochloride (111 mg, 0.56 mmol) at room temperature, and the mixture is stirred at about 45° C. for 5 hours. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water and a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (ethyl acetate:hexane=3:2→3% ethanol/ethyl acetate) to give the title compound (168 mg, 0.25 mmol) as amorphous.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06420381B1 |
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| Source dataset | uspto-grants-2002_07 |
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| ORD ID | ord-94a16ad4dae94b948a5a584f38ca2e92 |
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| Source note | uspto-grants-2002_07 |
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