Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-Chloro-3-nitropyridin-2-ylamine | HCID 2724035 | — |
| Reactant | HCID 89854330 | HCID 89854330 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 117966410 | HCID 117966410 | 68% |
Reaction Steps
To a solution of N,N,4-trimethylpiperidine-3-carboxamide (0.16 g, 0.96 mmol) in dimethylsulfoxide (5 mL) were added triethylamine (0.2 mL, 0.96 mmol) and 6-chloro-3-nitropyridin-2-amine (0.168 g, 0.96 mmol). The reaction mixture was heated for 12 h at 80° C., then was cooled. The mixture was diluted with water and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography to afford cis-1-(6-amino-5-nitropyridin-2-yl)-N,N,4-trimethylpiperidine-3-carboxamide (0.2 g, 68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09296745B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-68b50260ba8e41b18a1f47c992a775ed |
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| Source note | uspto-grants-2016_03 |
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