2,2,2-Trifluoroethanol → HCID 86729358, compound

2,2,2-Trifluoroethanol (1.6 mL, 22 mmol) and TEA (6.2 mL, 45 mmol) were dissolved in acetonitrile (200 mL). N,N-disuccinimidyl carbonate (8.6 g, 34 mmol) was added and the resulting mixture was stirred at ambient temperature for 90 minutes. 4-(Cyanomethylidene)piperidinium trifluoroacetate (5.3 g, 23 mmol) in DMSO (10 mL) was then added, followed by TEA (6.2 mL, 45 mmol). The resulting mixture was stirred at 50° C. for 16 hours. The reaction mixture was cooled to ambient temperature, diluted with EtOAc and washed sequentially with saturated NaHCO3 (aq) and water. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-5% MeOH in DCM) to afford the title compound. LRMS (ESI) calc'd for C10H11F3N2O2 [M+H]+: 249. Found: 249.

1. stirringThe resulting mixture was stirred at 50° C. for 16 hours
2. temperatureThe reaction mixture was cooled to ambient temperature
3. washwashed sequentially with saturated NaHCO3 (aq) and water
4. dry with materialThe organic layer was dried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by MPLC on silica gel (
8. washa gradient elution of 0-5% MeOH in DCM)

ORD record

ord-473851a1fa574222847573e6680bc85a

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328099B2