Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | [1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acid | HCID 1512539 | — |
| Reactant | 2-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine | HCID 23153198 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23153518 | HCID 23153518 | 43.1% |
Reaction Steps
2-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine (400 mg) was dissolved in dimethylformamide (4.0 ml) under nitrogen atmosphere. To the solution were added 2-[1-(tert-butoxycarbonyl)piperidin-4-yl]acetic acid (487 mg), triethylamine (0.335 ml) and BOP reagent (1.06 g) at room temperature, followed by stirring at 60° C. for 3 hours. The reaction mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was purified by silica gel column chromatography (eluent; ethyl acetate:heptane=1:2 to 1:1) to provide the titled compound (328 mg, 43%) as pale yellow 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-dbdd2b08f9f046c08b9ac724d20ded0b |
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| Source note | uspto-grants-2009_05 |
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