Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Oxalyl chloride | HCID 65578 | — |
| Edukt | 2-Chloropyridin-4-amine | HCID 84432 | — |
| Edukt | (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl]prop-2-enoic acid | HCID 69057218 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | HCID 86760957 | HCID 86760957 | — |
Reaktionsschritte
To a solution of (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (300 mg, 0.808 mmol) in THF (3 ml) were added DMF (0.03 ml) and oxalylchloride (0.0846 ml, 0.970 mmol), the mixture was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 4-amino-2-chloropyridine (209 mg, 1.62 mmol), triethylamine (0.451 ml, 3.24 mmol) and THF (3 ml), and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane ethyl acetate=2:1) to give the objective product as a solid material.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US07582651B2 |
|---|
| Quelldatensatz | uspto-grants-2009_09 |
|---|
| ORD ID | ord-566b07f425d148629825519ca0a9c9fb |
|---|
| Quellennotiz | uspto-grants-2009_09 |
|---|