Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate | HCID 11334154 | — |
| Reactant | HCID 178420751 | HCID 178420751 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66842146 | HCID 66842146 | 72.9% |
Reaction Steps
1.39 ml (8.40 mmol) of diisopropylethylamine are added to a suspension of 0.840 g (7 mmol) of 1H-[1,2,3]triazolo[4,5-b]pyridine, of 1.741 g (7 mmol) of tert-butyl 4-chlorocarbonylpiperazine-1-carboxylate (Bioorg. Med. Chem. Lett. 2000, 10, 2357) and of 0.042 g (0.35 mmol) of 4-dimethylaminopyridine in 14 ml of tetrahydrofuran. The mixture is stirred at ambient temperature for 4 hours and then 80 ml of ethyl acetate and 20 ml of water are added. The organic phase is separated by settling out and is then washed with 3×20 ml of water and 20 ml of a saturated aqueous solution of sodium chloride. The product is dried over sodium sulfate and evaporated to dryness. The residue is recrystallized from isopropanol, so as to obtain 1.70 g (5.1 mmol) of product in the form of white crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07868007B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-56f3b6d9115647808e5d5e0f0e78ffdb |
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| Source note | uspto-grants-2011_01 |
|---|