Diisopropylethylamine → HCID 178467067, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ((trans-4-((3-acetyl-6-bromoquinolin-4-yl)amino)cyclohexyl)methyl methanesulfonate (300 mg, 0.66 mmol) and tert-butyl piperazine-1-carboxylate (566 mg, 3.0 mmol) in acetonitrile (5 mL) and dioxane (5 mL) was added KI (500 mg, 3.0 mmol) and N,N-diisopropylethylamine (0.60 mL, 3.44 mmol) and the reaction mixture was heated at 70° C. for 16 h. The solution was cooled to room temperature, diluted with satd. aq. NaHCO3 and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica, 0-20% methanol/dichloromethane) to afford the desired product (248 mg, 69%) as an off-white solid. ESI MS m/z 545 [C27H37BrN4O3+H]+

Provenance & Evidence