page_title: Atevirdine
section_title: Synthesis
hierarchical_section_title: Atevirdine / Synthesis
caption_attribution_description: English: D. L. Romero, Drugs Future 19, 9 (1995).
context_page_description: Ateviridine is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of HIV.
context_section_description: 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. Reaction of the resulting amine with the imidazolide derivative of 5-methoxy-3-indoleacetic acid produces the amide reverse transcriptase inhibitor, atevirdine.
caption: Atevirdine synthesis:[2][3] SAR:[4]
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