HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}pyrazine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 2-Pyrazinecarboxylic acid | HCID 1047 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 69001756 | HCID 69001756 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}pyrazine-2-carboxamide | HCID 69004090 | 30% |
Reaction Steps
(E)-2-[2-(1H-indazol-3-yl)vinyl]phenylamine (60 mg, 0.26 mmol) was dissolved in THF (5 mL) and the solution was added with 2-pyrazinecarboxylic acid (38 mg, 0.31 mmol), 1-hydroxybenzotriazole monohydrate (51 mg, 0.33 mmol), 4-methylmorpholine (47 μL, 0.51 mmol) and EDC (68 mg, 0.36 mmol), followed by stirring at room temperature for 3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethanol to obtain Compound 28 (25 mg, 30%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07605272B2 |
| Source dataset | uspto-grants-2009_10 |
| ORD ID | ord-98a57dacc1a44ca6860685d2fe1b6661 |
| Source note | uspto-grants-2009_10 |