Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4,6-Dichloronicotinamide | HCID 600044 | — |
| Reactant | 2,6-Dichloropyridine-3-carboxamide | HCID 22142778 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 57969191 | HCID 57969191 | 54% |
Reaction Steps
To a solution of 2,6-dichloro-nicotinamide (1) (2.3 g, 12.2 mmol) in acetonitrile (anhydrous, 100 mL) were added 2-benzylamine (2) (1.3 g, 12.2 mmol) and triethylamine (1.7 mL, 12.2 mmol). The reaction was heated at 60° C. for 4 hours. The solution was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. Purification was achieved by Biotage silica gel chromatography with 5%-50% EtOAc/hexanes gradient to afford 1.71 g (54% yield) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.82 (br. s., 1H), 7.52 (d, J=8.2 Hz, 1H), 7.40-7.23 (m, 6H), 6.50 (d, J=8.2 Hz, 1H), 5.66 (br. s., 2H), 4.70 (d, J=5.5 Hz, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08461135B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-f97bf2dbc0764d0aa23b3e172dffc5d0 |
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| Source note | uspto-grants-2013_06 |
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