HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 58754846, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-(Piperidin-1-yl)aniline | HCID 458795 | — |
| Reactant | PyBroP | HCID 2733179 | — |
| Reactant | potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate | HCID 67188357 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58754846 | HCID 58754846 | 85% |
Reaction Steps
To a mixture of 2-piperidin-1-yl-phenylamine (63.5 mg, 0.360 mmol), potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 11, step (d), 100 mg, 0.327 mmol) and PyBroP (152 mg, 0.327 mmol) in 4 mL of 1,2-dichloroethane was added DIEA (171 μL, 0.981 mmol). After stirring at RT for 16 h under Ar, the mixture was treated with 50 mL of EtOAc, washed with H2O (2×10 mL) and brine (10 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (5-10% EtOAc/hexane) to afford 118 mg (85%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C22H31N5O2Si, 426.2 (M+H), found 426.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07790724B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-bb4cd39d7c524d149628a9db3e221df3 |
| Source note | uspto-grants-2010_09 |