Ethylmorpholine → N-[(2-chloro-4-fluorophenyl)methyl]-1-methyl-5-oxo-prolinamide

1-Methyl-5-oxo-proline (0.050 g, 0.35 mmol, prepared as described below) was dissolved in anhydrous dichloromethane (˜7 ml) and to this was added 1-hydroxybenzotriazole (0.047 g, 0.42 mmol), [(2-chloro-4-fluorophenyl)methyl]amine (0.056 ml, 0.42 mmol), N-ethyl morpholine (0.166 ml, 1.04 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.067 g, 0.42 mmol). The mixture was stirred at room temperature overnight. A further aliquot of [(2-chloro-4-fluorophenyl)methyl]amine (0.100 ml, 0.8 mmol) was added to the mixture and stirring continued for a while longer but HPLC indicated that no further product was forming. The mixture was washed sequentially with 2M aqueous hydrogen chloride (5 ml) and saturated aqueous sodium hydrogen carbonate (5 ml). The organic layer was collected and evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give pure N-[(2-chloro-4-fluorophenyl)methyl]-1-methyl-5-oxo-prolinamide (0.015 g) as a white solid. LC/MS [M+H]+=285, retention time=2.04 minutes.

1. stirringstirring
2. customwas forming
3. washThe mixture was washed sequentially with 2M aqueous hydrogen chloride (5 ml) and saturated aqueous sodium hydrogen carbonate (5 ml)
4. customThe organic layer was collected
5. customevaporated
6. customto give the crude product
7. customThe crude material was purified

ORD-Eintrag

ord-0c2b4d86cafb47f19b03133c961dbc37

Quelldatensatz

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07718693B2