Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Bromo-3-chloropropane | HCID 8006 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 12972101 | HCID 12972101 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22105972 | HCID 22105972 | 88.7% |
Reaction Steps
To a solution of N-{1-butyl-4-(3-hydroxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl}-N'-(2,6-diisopropylphenyl)urea (1000 mg, 1.95 mmol) and 1-bromo-3-chloropropane (460 mg, 2.93 mmol) in DMF (10 ml) was added potassium carbonate (673 mg, 4.88 mmol), and the mixture was stirred at 50°-60° C. for 6 hours. After allowed to stand for cooling, the mixture was poured into water, extracted with ethyl acetate, washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The residue was concentrated under reduced pressure, purified by silica gel column chromatography (ethyl acetate:hexane=50:50), and crystallized from hexane to give the title compound (1020 mg, 1.73 mmol) as a colorless powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05843957 |
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| Source dataset | uspto-grants-1998_12 |
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| ORD ID | ord-a61eca14c03943db9f1f5e37935aa787 |
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| Source note | uspto-grants-1998_12 |
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