Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (S)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethyl methanesulfonate | HCID 117842947 | — |
| Reactant | HCID 117844063 | HCID 117844063 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 117843516 | HCID 117843516 | — |
Reaction Steps
6-chloropyrazolo[1,5-a]pyridin-4-ol (120 mg, 0.712 mmol), (S)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethyl methanesulfonate 1.30 (365 mg, 1.07 mmol) and cesium carbonate (278 mg, 0.854 mmol) were suspended in DMF (2.0 mL). The mixture was heated at 90° C. for 3 h. After cooling to room temperature, the mixture was poured into a saturated aqueous solution of NaHCO3 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (30-100% EtOAc in hexanes) on silica gel to afford (R)-4-((R)-1-((6-chloropyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376441B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-d49e7d0a7063499887a875b7d6c2ea5c |
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| Source note | uspto-grants-2016_06 |
|---|