Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Methyl 2-aminopyridine-3-carboxylate | HCID 351633 | — |
| Reactant | HCID 58420519 | HCID 58420519 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 67394627 | HCID 67394627 | 33% |
Reaction Steps
In the same manner as that of Example 9, 4,5-diisopropylthiophene-2-carboxylic acid (180 mg, 0.849 mmol) was converted to an acid chloride with thionyl chloride and dimethylformamide. This acid chloride was dissolved in pyridine (4 ml), the solution was added with methyl 2-aminopyridine-3-carboxylate (258 mg, 1.70 mmol) and 4-dimethylaminopyridine (5 mg, 41 μmol), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was treated in a conventional manner, and then the resultant was purified by silica gel chromatography [benzene-ethyl acetate (4:1)] to obtain methyl 6-[(4,5-diisopropylthiophene-2-carbonyl)amino]pyridine-3-carboxylate (98 mg, 33%) as colorless foam, together with the collected starting material (67 mg, 37%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722730B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-0a63f75389e1423a9cabede3a12ddcc5 |
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| Source note | uspto-grants-2014_05 |
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