Dimethylformamide → 4-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide

Participants

Reaction Steps

Amide 1-6 was made from acid chloride 1-5 (810 mg, 2.96 mmol) as one member of a 96 compound library, employing the technique of parallel synthesis using the Myriad Core System/nMiniblock. According to the general procedure, 0.10 mmol of each amine (2-adamantylamine for this product) was weighed into the miniblock reaction tubes, and 0.350 ml of dry DMF and 0.55 ml of dry diisopropylethylamine was added to each tube. A 0.25 M solution of the acid chloride in dry acetonitrile was prepared, and 0.400 ml of this solution was dispensed to each tube and the reactions were incubated and stirred overnight under an inert nitrogen atmosphere. The products were purified using a Fraction Lynx HPLC (with detection according to mass spectrum) equipped with a Waters Xterra MS C18 5 um 19×50 nm reverse phase column running a gradient of water/acetonitrile (0.1% TFA). The fractions containing product were concentrated to remove some of the acetonitrile and the lyophilized to provide pure product 4-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide 1-6 as a white fluffy amorphous solid.

Provenance & Evidence