Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Cyclopropanecarbonyl chloride | HCID 77637 | — |
| Reactant | N-(4-Fluorophenyl)-N'-[4-(2-aminopyridin-4-yloxy)-3-fluorophenyl]malonamide | HCID 23153333 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23153505 | HCID 23153505 | 53% |
Reaction Steps
N-(4-Fluorophenyl)-N′-[4-(2-aminopyridin-4-yloxy)-3-fluorophenyl]malonamide (34 mg) was dissolved in N,N-dimethylformamide (0.5 ml), and then triethylamine (0.047 ml) and cyclopropanecarbonyl chloride (0.016 ml) were added dropwise thereto under a nitrogen atmosphere at room temperature, followed by stirring for 1 hr. To the reaction mixture were added a 1 N aqueous solution of sodium hydroxide (1.5 ml) and methanol (1.0 ml), followed by stirring and extracting with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of ammonium chloride in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a residue, which was then dried in vacuum to provide the titled compound (21.1 mg, 53%) as white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07531532B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-b1550135e24e4429975e07267935a9ac |
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| Source note | uspto-grants-2009_05 |
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