Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | HCID 66939445 | HCID 66939445 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66939708 | HCID 66939708 | 35% |
Reaction Steps
To a solution (3 mL) of the compound (200 mg, 0.43 mmol) obtained in Example 95f in N,N-dimethylformamide were added 2-pyridinecarboxylic acid (64 mg, 0.52 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (99 mg, 0.52 mmol), 1-hydroxybenzotriazole (80 mg, 0.52 mmol) and triethylamine (0.12 mL, 0.86 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=30/70) to give the title compound (79 mg, 35%) as a pale-orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08461348B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-faa3dc5d500d4dc5a079254a58c38820 |
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| Source note | uspto-grants-2013_06 |
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