HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → [5-(4-Ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Ethylpiperazine | HCID 79196 | — |
| Reactant | (6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonate | HCID 86641141 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [5-(4-Ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl ester | HCID 66914627 | 90% |
Reaction Steps
A mixture of methanesulfonic acid 6-tert-butoxycarbonylamino-pyridin-3-ylmethyl ester (Step 26.3) (0.8 g, 2.6 mmol), N-ethylpiperazine (0.37 mL, 2.9 mmol, 1.1 equiv), cesium carbonate (1 g, 3.2 mmol, 1.2 equiv), and DMF (10 ml) was stirred for 2 h at rt, diluted with EtOAc and H2O, and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to provide a yellow solid. Trituration in Et2O afforded 0.75 g of the title compound as a white solid: ES-MS: 321.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536175B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-67ab2e417bfa4908aed9eb3b06809570 |
| Source note | uspto-grants-2013_09 |