Diisopropylethylamine → HCID 86616966, compound

Participants

Reaction Steps

To a solution of 1.0 g (0.0028 mol) of 5-bromo-6-(4-trifluoromethoxy-phenyl)-pyrazine-2-carboxylic acid in 80.0 ml dichloromethane was added at room temperature 0.4 ml (0.405 g 0.0030 mol) (1-chloro-2-methyl-propenyl)-dimethyl-amine and the mixture was stirred for 0.5 hours. To the resulting dark solution was added 0.35 g (0.0030 mol) (1R,2R)-2-amino-cyclohexanol and 0.94 ml (0.712 g, 0.0060 mol) N-ethyldiisopropylamine and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic phase washed with 10% aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of 100% heptane to heptane with 40% ethyl acetate to yield 1.107 g of the tile compound as a white waxy solid. MS (ISP) (M+H+)=360.0 and 362.0.

Provenance & Evidence