HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-[(6-bromopyridin-2-yl)methyl]-2-cyanoacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyanoacetic acid | HCID 9740 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 1-(6-Bromopyridin-2-yl)methanamine--hydrogen chloride (1/1) | HCID 45789886 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-[(6-bromopyridin-2-yl)methyl]-2-cyanoacetamide | HCID 59526353 | — |
Reaction Steps
6-Bromo-2-pyridinemethanamine hydrochloride (0.25 g, 1.12 mmol) was taken up in DMF (8.4 mL) and triethylamine (0.31 mL, 2.24 mmol) was added. After five minutes, cyanoacetic acid (0.095 g, 1.12 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.21 g, 1.12 mmol), 1-hydroxybenzotriazole hydrate (0.18 g, 1.14 mmol) were added and the reaction was maintained at room temperature overnight. Upon completion the mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08367706B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-d9570feb955744e3a5b2f02a1eb1a374 |
| Source note | uspto-grants-2013_02 |