Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate | HCID 2824057 | — |
| Reactant | HCID 68579996 | HCID 68579996 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68582033 | HCID 68582033 | 30.6% |
Reaction Steps
3,4-Dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1; 0.500 g, 2.00 mmol), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (0.625 g, 2.00 mmol) and sodium bicarbonate (0.336 g, 2.00 mmol) were stirred in DMF (5 ml). The reaction was heated to 50° C. overnight. The solution was diluted by the addition of water and the resulting layers were separated. The aqueous layer was extracted with EtOAc (3×), and the organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. Hexanes were added to the crude material, and the precipitate was filtered and rinsed with EtOAc to give the title compound as a beige solid (0.273 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07709503B2 |
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| Source dataset | uspto-grants-2010_05 |
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| ORD ID | ord-c4f4974fe98e4224aa282594f234ca0b |
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| Source note | uspto-grants-2010_05 |
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