Atevirdine

Synthesis

Preparation of the pyridylpiperazine moiety starts by aromatic displacement of chlorine from 2-Chloro-3-nitropyridine by piperazine to give 3. The secondary amine is then protected as its BOC derivative by reaction with Di-tert-butyl dicarbonate (Boc anhydride) to give 4. The nitro group is then reduced by catalytic hydrogenation. Reductive alkylation with acetaldehyde in the presence of lithium cyanoborohydride gives the corresponding N-ethyl derivative. The protecting group is then removed by reaction with TFA. Reaaction of the resulting amine with the imidazolide derivative of 5-Methoxy-3-indoleacetic acid affords the amide reverse transcriptase inhibitor, atevirdine.