Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 178487293 | HCID 178487293 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178487291 | HCID 178487291 | 78.9% |
Reaction Steps
Triethyl amine (0.39 ml, 2.77 mmol) was added to solution of HATU (1.05 g, 2.77 mmol) and trans-4-(6-Methoxy-3-methyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexanecarboxylic acid (0.8 g, 2.5 mmol) in DMF (15 ml). The mixture was stirred at room temperature for 20 minutes and then tert-butyl-1-piperazinecarboxylate (0.47 g, 2.52 mmol) was added. The mixture was stirred at room temperature overnight, the solvent was removed under reduced pressure and the crude product was dissolved in DCM (50 ml). The organic solution was washed with HCl 1M (2×40 ml) and then with a saturated solution of NaHCO3. The organic solution was dried over Na2SO4, filtered and the solvent removed. Purification by silica column using cyclohexane/EtOAc (8/1) as eluent gave the titled compound (960 mg, 78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08865704B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-25d83281913a45d391754aef2d1c7d4e |
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| Source note | uspto-grants-2014_10 |
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