Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(1-Hydroxycyclopropyl)ethyl methanesulfonate | HCID 86640792 | — |
| Reactant | N-(3-fluoro-4-((7-hydroxyquinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide | HCID 136347997 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 59278563 | HCID 59278563 | 31.2% |
Reaction Steps
To a mixture of N-(3-fluoro-4-(7-hydroxyquinolin-4-yloxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (735.7 mg, 1.52 mmol) and 2-(1-hydroxycyclopropyl)ethyl methanesulfonate (3.04 mmol) in 8 mL of N,N-dimethylacetamide was added cesium carbonate (4.955 g, 15.2 mmol). After stirring at 40° C. for 1 day, the reaction was quenched with water (5 mL) and extracted with CH2Cl2 (20 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on a silica gel column (CH2Cl2/CH3OH (v/v)=45:1) to afford the title compound as a white solid (270 mg, 15.6%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08232294B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-f6971b03c2bc4b5d880a9c36f154ccba |
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| Source note | uspto-grants-2012_07 |
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