HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,1'-Carbonyldiimidazole → (S)-N-(5-((R)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Edukt | (3S)-pyrrolidin-3-ol | HCID 2733874 | — |
| Edukt | (R)-5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine | HCID 67328765 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | (S)-N-(5-((R)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide | HCID 58386263 | 78,1% |
Reaktionsschritte
To a DCM (1 mL) solution of (R)-5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (25 mg, 0.084 mmol) was added CDI (27 mg, 0.17 mmol) at ambient temperature in one portion. After stirring for two hours, (S)-pyrrolidin-3-ol (15 mg, 0.17 mmol) was added in one portion. The reaction was stirred overnight before it was concentrated and directly purified by reverse-phase column chromatography, eluting with 0 to 40% acetonitrile/water to yield the final product as a solid (27 mg, 78% yield). MS (apci) m/z=412.2 (M+H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09447104B2 |
| Quelldatensatz | uspto-grants-2016_09 |
| ORD ID | ord-bbc0085fd8ec45a39d4ea52682ffd833 |
| Quellennotiz | uspto-grants-2016_09 |