atevirdine atevirdine atevirdine is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of hiv. atevirdine names preferred iupac name (5-methoxy-1h-indol-2-yl)methanone identifiers cas number 136816-75-6 n 3d model (jsmol) interactive image chembl chembl280527 y chemspider 54835 y pubchem cid 60848 unii n24015wc6d y comptox dashboard (epa) dtxsid40159940 inchi inchi=1s/c21h25n5o2/c1-3-22-18-5-4-8-23-20(18)25-9-11-26(12-10-25)21(27)19-14-15-13-16(28-2)6-7-17(15)24-19/h4-8,13-14,22,24h,3,9-12h2,1-2h3 ykey: ucpomlwzwrtiaa-uhfffaoysa-n yinchi=1/c21h25n5o2/c1-3-22-18-5-4-8-23-20(18)25-9-11-26(12-10-25)21(27)19-14-15-13-16(28-2)6-7-17(15)24-19/h4-8,13-14,22,24h,3,9-12h2,1-2h3key: ucpomlwzwrtiaa-uhfffaoyak smiles o=c(n2ccn(c1ncccc1ncc)cc2)c4cc3cc(oc)ccc34 properties chemical formula c21h25n5o2 molar mass 379.46 g/mol except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references synthesis atevirdine synthesis: sar: 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.