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. Author manuscript; available in PMC: 2022 Jul 22.
Published in final edited form as: J Med Chem. 2021 Jul 12;64(14):9960–9988. doi: 10.1021/acs.jmedchem.1c00184

Scheme 3:

Scheme 3:

Synthesis of compounds (±)-6g-la

aReagents and conditions: a) Appropriate aryl aldehyde, Cs2CO3, dioxane, 110 °C, 14 h 89–100%; b) for 23a-c: phenylhydrazine, AcOH, 80 °C, 14 h; for 23d: 4-methoxyphenylhydrazine, AcOH, 80 °C, 14 h, 30–48%; c) NaBH4, MeOH, 25 °C, 12 h or H2, Pd/C, MeOH, 25 °C, 12 h, 50–79%; d) for (±)-25a-c and 25f: methyl 4-formylbenzoate, EtOH, AcOH, NaBH3CN, 40 °C, 14 h; for (±)-25d: 20, EtOH, AcOH, NaBH3CN, 40 °C, 14 h; for (±)-25e: 16, NaBH(OAc)3 DCM, 40 °C, 14 h, 20–84%; e) NH2OH (50% in H2O), KOH, DCM/MeOH from 0 °C to 25 °C, 12 h, 18–79%.