Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 16753952 | HCID 16753952 | — |
| Reactant | Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate | HCID 22343006 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22346388 | HCID 22346388 | — |
Reaction Steps
A mixture of 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylic acid methyl ester (1.00 g, 3.53 mmol, see Example 113), 2-(aminomethyl)-5-fluoro-N,N-dimethylbenzenesulfonamide (1.64 g, 7.07 mmol), and triethylamine (0.99 mL, 7.07 mmol) in EtOH (8 mL) and DMF (2 mL) was heated to 78° C. overnight. The mixture was cooled to 40° C. and glacial acetic acid (0.81 mL, 14.1 mmol) was added. The mixture was allowed to cool to room temperature and water was added dropwise while sonicating to facilitate the product precipitating out of solution. The solids were collected by vacuum filtration to afford the desired product as a light yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06921759B2 |
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| Source dataset | uspto-grants-2005_07 |
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| ORD ID | ord-37942bb80a234eb58aab379bf1569272 |
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| Source note | uspto-grants-2005_07 |
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