Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 59714998 | HCID 59714998 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59714851 | HCID 59714851 | 71.9% |
Reaction Steps
[1-[2-[4-[N-(5-Methylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetic acid (909 mg), ammonium chloride (216 mg), benzotriazol-1-yloxytrispyrrolidinophosphonium hexafluorophosphate (1.56 g), 1-hydroxybenzotriazole hydrate (470 mg) and N,N-diisoprpoylamine (1.4 mL) were dissolved in N,N-dimethylformamide (8 mL). The solution was stirred at room temperature for 22 hours. Saturated aqueous sodium bicarbonate solution was added to the solution, and it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then, the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography (silica gel, chloroform:methanol=10:1) to give the title compound (652 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07375115B2 |
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| Source dataset | uspto-grants-2008_05 |
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| ORD ID | ord-3e73865b2e0248faa13c2097f874ef02 |
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| Source note | uspto-grants-2008_05 |
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