Atevirdine is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of HIV.
[1] Preparation of the pyridylpiperazine moiety starts by aromatic displacement of chlorine from 2-chloro-3-nitropyridine by piperazine to give 3.
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.
Reaction of the resulting amine with the imidazolide derivative of 5-methoxy-3-indoleacetic acid produces the amide reverse transcriptase inhibitor, atevirdine.