Atevirdine

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.

Atevirdine synthesis: [ 2 ] [ 3 ] SAR : [ 4 ]