HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyanogen Bromide → 4-[(1R,2S)-2-(2-{[3-methyl-5-(2-oxoimidazolidin-1-yl)pyridine-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyanogen Bromide | HCID 10476 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(5-methyl-6-{2-[(1S,2R)-2-piperidin-4-ylcyclopropyl]ethoxy}pyridine-3-yl)imidazolidin-2-one | HCID 86711188 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[(1R,2S)-2-(2-{[3-methyl-5-(2-oxoimidazolidin-1-yl)pyridine-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carbonitrile | HCID 86711189 | — |
Reaction Steps
To a solution of 1-(5-methyl-6-{2-[(1S,2R)-2-piperidine-4-ylcyclopropyl]ethoxy}pyridine-3-yl)imidazolidin-2-one (12 mg, 0.035 mmol) in 1.5 mL of DCM was added K2CO3 (14.5 mg, 0.105 mmol, in 0.5 mL of water) at room temperature followed by addition of cyanogen bromide (0.014 mL of 3M soln in DCM, 0.042 mmol) via syringe at room temperature. The mixture was then stirred for 30 min at room temperature and then diluted with 2 mL DCM. The solution was washed with sat'd NaHCO3 aq. soln, separated, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The crude product was used without further purification. LCMS (ESI) m/z 370 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08957062B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-ccf2b6975b1b4b5593f2c8e4648567af |
| Source note | uspto-grants-2015_02 |