Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | PyBroP | HCID 2733179 | — |
| Reactant | HCID 68451726 | HCID 68451726 | — |
| Reactant | 4-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt | HCID 178510383 | — |
| Product | HCID 59128572 | HCID 59128572 | 55% |
Reaction Steps
A mixture of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-[1,2,4]-triazole-3-carboxylic acid potassium salt (as prepared above, 28 mg, 0.10 mmol), DIEA (34 μL, 0.20 mmol), 4-(4-amino-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in Example 14, step (b), 35.6 mg, 0.100 mmol) and PyBroP (69.9 mg, 0.150 mmol) in DCM (2 mL) was stirred at RT for 12 h. The reaction mixture was diluted with DCM (5 mL) and washed with saturated aqueous NaHCO3 (10 mL) and water (10 mL). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo The product was chromatographed on silica (20-40% EtOAc/hexane) to obtain the title compound (31.9 mg, 55%). Mass psectrum (ESI, m/z): Calcd. for C13H47N5O4Si, 481.2 (M-BOC+2H), found. 481.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07645755B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-5477e8fc3d3447759e8212c03ff2cc39 |
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| Source note | uspto-grants-2010_01 |
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