Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 86681873 | HCID 86681873 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 56592241 | HCID 56592241 | 35% |
Reaction Steps
Under an argon atmosphere, anhydrous methylene chloride (0.5 mL) and triethylamine (10 μL, 0.069 mmol) were added to N-[2-fluoro-4-(methylsulfonyl)phenyl]-7-(piperidin-4-yl)furo[3,2-d]pyrimidine-4-amine hydrochloride (10 mg, 0.023 mmol), picolinic acid (3.3 mg, 0.028 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9 mg, 0.046 mmol) and N,N-dimethylaminopyridine (0.3 mg, 0.002 mmol), followed by stirring at room temperature for 2 hours. Water was added to the reaction liquid, the reaction liquid was extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=20:1) to give the titled compound (3.3 mg, 35%) as a yellow oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765771B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-7067569094344fc1ad1693b2ef8b4030 |
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| Source note | uspto-grants-2014_07 |
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