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. 2023 Nov 3;15(21):5283. doi: 10.3390/cancers15215283

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© 2023 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).

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Scheme 1 — Synthesis of compounds 1–23. Reagents and conditions: (a) NaOH, THF-H₂O, 50 °C, 5 h; (b) 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, N,N-diisopropylethylamine, DMF, 4-aminomethyl-1-Boc-piperidine, 12 h; (c) aryl boronic acid or aryl 4,4,5,5-tetramethyl-1,3,2-dioxaborolane, tetrakis(triphenylphosphine)palladium, Na₂CO₃, 1,4-dioxane-H₂O, 100 °C; (d) HCl (4 N in 1,4-dioxane), CH₂Cl₂, 0 °C; (e) trifluoroacetic anhydride, 0 °C to room temperature, 2 h; (f) NaOH (20% aq.), 80 °C, 2 days; (g) 4-aminomethyl-1-Boc-piperidine, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, 1-hydroxybenzotriazole, triethylamine, CH₂Cl₂.