Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-(Dimethylamino)propyl chloride hydrochloride | HCID 94308 | — |
| Reactant | HCID 12972101 | HCID 12972101 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22106431 | HCID 22106431 | 37.6% |
Reaction Steps
To a suspension of N-{ 1-butyl-4-(3-hydroxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl}-N'-(2,6-diisopropylphenyl)urea (200 mg, 0.4 mmol), potassium carbonate (166 mg, 1.2 mmol), and sodium iodide (5 mg) in DMF (10 ml) was added 3-dimethylaminopropyl chloride hydrochloride (63 mg) at room temperature, and the mixture was stirred at 60°-70° C. for 10 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 magnesium sulfate. The residue was concentrated under reduced pressure, and purified by silica gel column chromatography (10% methanol in chloroform) to give the title compound (88 mg, 0.15 mmol).
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-cb31ddbd38da4c9fb09328f8fa88baf0 |
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| Source note | uspto-grants-1998_12 |
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