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MK-8527 is a novel inhibitor of HIV-1 reverse transcriptase translocation with potential for extended-duration dosing

Fig 11

Synthesis of MK-8527.

Reagents and conditions: (a) acetyl chloride, methanol (MeOH); (b) p-toluoyl chloride, pyridine; (c) HCl, diethyl ether; (d) 2,6-dichloro-7-deazapurine, NaH, acetonitrile (MeCN); (e) ammonia in isopropanol, sodium methoxide (NaOMe) in methanol (MeOH); (f) TBSCl, imidazole, N,N-dimethylformamide; (g) trifluoroacetic acid (TFA), tetrahydrofuran (THF), H2O; (h) IBX, MeCN, dimethyl sulfoxide (DMSO); (i) 1. formaldehyde, NaOH, 2. NaBH4, ethanol; (j) IBX, MeCN; (k) Bestmann−Ohira reagent, K2CO3; (l) TBAF, THF.

Fig 11

doi: https://doi.org/10.1371/journal.pbio.3003308.g011