HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,1'-Carbonyldiimidazole → (R)-N-(5-((R)-2-(2-chloro-5-fluorophenyl)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-(2-chloro-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine | HCID 67330330 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | (R)-N-(5-((R)-2-(2-chloro-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide | HCID 58386342 | 67,4% |
Reaktionsschritte
To a DCM (0.8 mL) solution of (R)-5-(2-(2-chloro-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (10 mg, 0.030 mmol, prepared as described in Example 8) was added CDI (10 mg, 0.06 mmol) at ambient temperature in one portion. After stirring two hours, (S)-pyrrolidin-3-ol (5 mg, 0.06 mmol) was added in one portion. The reaction was stirred at ambient temperature for 20 hours before it was concentrated and directly purified by reverse-phase column chromatography, eluting with 5 to 50% acetonitrile/water to yield the final product as a solid (9 mg, 67% yield). MS (apci) m/z=445.2 (M+H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09447104B2 |
| Quelldatensatz | uspto-grants-2016_09 |
| ORD ID | ord-65fe947a455c46a4b48da716ac67dacf |
| Quellennotiz | uspto-grants-2016_09 |