Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Propanesulfonyl chloride | HCID 66279 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 67378126 | HCID 67378126 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53353586 | HCID 53353586 | — |
Reaction Steps
A solution 3-(2-Amino-3,5-difluoropyridin-4-yl)-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one (15 mg, 0.05 mmol), triethylamine (3 ml), and DCM (10 mL) was treated with n-propanesulfonyl chloride (0.05 ml, 0.4 mmol) at 0° C. The mixture was allowed to warm to rt and was stirred for 16 h. Aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was dissolved in methanol (10 mL) and potassium carbonate (2 g) was added. The mixture was stirred at room temperature for 2 h. Water was added and the mixture was extracted with ethyl acetate, then the combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel (2% to 3% methanol in DCM eluant) to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09181238B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-10340ad38f7441fc98f81b4b5b1c28ad |
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| Source note | uspto-grants-2015_11 |
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