Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Benzylpiperazine | HCID 75994 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 68527032 | HCID 68527032 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68524472 | HCID 68524472 | — |
Reaction Steps
To a solution of (1-{4-[5-(3,4-dichlorobenzenesulfonylamino)pyridin-2-yloxy]-3-methylphenyl}piperidine-4-yl)acetic acid (1.70 g, 3.1 mmol) and 1-benzylpiperazine (0.71 g, 4.0 mmol) in DMF (40 mL) were added triethylamine (1.08 mL, 7.8 mmol) and diethyl cyanophosphonate (0.76 g, 4.3 mmol) under ice cooling, and the resulting solution was stirred for 1 hour under ice cooling. To this reaction solution was added a saturated sodium bicarbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1), after which the resulting product was recrystallized from ethanol, to thereby yield 1.61 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08236826B2 |
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| Source dataset | uspto-grants-2012_08 |
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| ORD ID | ord-d2bdc0fc714b4367aed631fdb6c62d1c |
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| Source note | uspto-grants-2012_08 |
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