HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Chloroacetyl chloride → propan-2-yl 2-(cyclohexylmethylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Chloroacetyl chloride | HCID 6577 | — |
| Edukt | Piperidine | HCID 8082 | — |
| Edukt | Cyclohexanemethylamine | HCID 76688 | — |
| Edukt | Diisopropyl malonate | HCID 83223 | — |
| Edukt | 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde | HCID 5372812 | — |
| Edukt | Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate | HCID 51050080 | — |
| Lösungsmittel | Isopropanol | HCID 3776 | — |
| Produkt | propan-2-yl 2-(cyclohexylmethylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate | HCID 178459409 | 20% |
Reaktionsschritte
A solution of isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.44 mmol) which similarly prepared according to the procedure described in the Example 74, Third step using diisopropyl malonate and chloroacetyl chloride, and aminomethylcyclohexane (0.063 mL, 0.48 mmol) in 2-propanol (2.0 mL) was stirred at ambient temperature for 14 h. To this reaction mixture, 7-azaindole-3-carboxaldehyde (0.065 g, 0.44 mmol) and piperidine (0.0044 mL, 0.044 mmol) were added then the mixture was refluxed for further 8 days. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.036 g, y. 19%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08742113B2 |
| Quelldatensatz | uspto-grants-2014_06 |
| ORD ID | ord-20dde74e66a94bd095fda331e0a36e7d |
| Quellennotiz | uspto-grants-2014_06 |