Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzyl (3S)-piperidin-3-ylcarbamate | HCID 1514175 | — |
| Reactant | 3-Bromo-4-chloro-5-nitropyridine | HCID 12510052 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86726888 | HCID 86726888 | 91.9% |
Reaction Steps
A mixture of 3-bromo-4-chloro-5-nitropyridine (from Ark Pharm, 0.050 g, 0.21 mmol), benzyl (3S)-piperidin-3-ylcarbamate (0.059 g, 0.25 mmol), and triethylamine (0.088 mL, 0.63 mmol) in isopropyl alcohol (0.8 mL) was heated at 90° C. in a sealed vial for 16 h. The reaction mixture was diluted with EtOAc (40 mL) and water (3 mL). The layers were separated and the organic layer was washed with water (3×3 mL) and the combined aqueous phases were extracted with EtOAc (3 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the sub-title compound (0.084 g). The crude product was used without further purification in the subsequent reaction. LCMS (ESI) calc. for C18H20BrN4O4[M+H]+: m/z=435.1. found 435.0/437.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09278950B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-99ea7291633e465eb1d7b9e2ad710623 |
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| Source note | uspto-grants-2016_03 |
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