Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2-Bromopyridine-3-carboxylic acid | HCID 233262 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1433965-43-5 | HCID 90449362 | 60% |
Reaction Steps
In DMF (20 mL) was dissolved 2-bromonicotinic acid (2.00 g, 9.90 mmol). To this were added triethylamine (4.14 mL, 29.7 mmol), dimethylamine (2 mol/L solution in THF, 9.90 mL, 19.8 mmol), 1-hydroxybenzotriazole monohydrate (2.27 g, 14.85 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.85 g, 14.85 mmol), and the mixture was stirred at room temperature for 12 hours. A saturated aqueous ammonium chloride solution was added to the mixture and extraction with ethyl acetate was performed. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated from the filtrate under-reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give compound DA1 (1.40 g, 60% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09067923B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-c9e2a330ff274a81a862b5095b66dbb1 |
|---|
| Source note | uspto-grants-2015_06 |
|---|