HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → ethyl[(3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)piperidin-1-yl]acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Acetoxy-2-bromoethane | HCID 13564 | — |
| Reactant | 8-(cyclohexylmethoxy)-2-methyl-N-[(3S)-piperidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride | HCID 86713490 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ethyl[(3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)piperidin-1-yl]acetate | HCID 131737222 | — |
Reaction Steps
To a suspension of 307 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(3S)-piperidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride, 335 mg of potassium carbonate, 5 ml of acetonitrile, and 5 ml of DMF was added 92 μl of bromoethyl acetate under ice-cooling, followed by stirring for 3 hours under ice-cooling. To the reaction mixture were added water and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 299 mg of ethyl[(3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)piperidin-1-yl]acetate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447090B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-7e976c4e9c9f48098fa2f6a15b511287 |
| Source note | uspto-grants-2016_09 |