Atevirdine
Reverse-transcriptase inhibitor
From Wikipedia, the free encyclopedia
Atevirdine is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of HIV.[1]
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| Formula | C21H25N5O2 |
| Molar mass | 379.464 g·mol−1 |
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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. Reaction of the resulting amine with the imidazolide derivative of 5-methoxy-3-indoleacetic acid produces the amide reverse transcriptase inhibitor, atevirdine.
