Cesium carbonate → HCID 57559685, compound

Participants

Reaction Steps

To a mixture of tert-butyl 3-methyl-4-oxo-4,5-dihydro-2H-benzo[g]pyrazolo[4,3-c]quinoline-2-carboxylate (1-6) (0.1 g, 0.29 mmol, 1.0 equiv) and cesium carbonate (0.50 g, 1.5 mmol, 5.4 equiv) in DMF (5 ml) was added N-(3-bromopropyl)carbamic acid tert-butyl ester (0.12 g, 0.50 mmol, 1.8 equiv) and the reaction was stirred at room temperature. After 20 hours LC/MS indicated the reaction was 55% complete so an additional 120 mg of alkylating agent was added and the reaction was stirred at room temperature for an additional 24 hours. LC/MS indicated the reaction was complete, and the reaction was filtered to remove the base and purified by reverse phase liquid chromatography (H2O/CH3CN gradient w/0.05% NH4OH present) to yield tert-butyl 5-{3-[(tert-butoxycarbonyl)amino]propyl}-3-methyl-4-oxo-4,5-dihydro-2H-benzo[g]pyrazolo[4,3-c]quinoline-2-carboxylate (1-7) as a white solid. LRMS m/z (M+H) 507.6 found, 507.3 required.

Provenance & Evidence