HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | (3S)-pyrrolidin-3-ol | HCID 2733874 | — |
| Reactant | (R)-5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine | HCID 67328765 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (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% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08513263B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-365c132a8a7d4a49802079bc7a70fd66 |
| Source note | uspto-grants-2013_08 |