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. Author manuscript; available in PMC: 2022 Apr 22.
Published in final edited form as: J Med Chem. 2021 Mar 31;64(8):5099–5122. doi: 10.1021/acs.jmedchem.1c00164

Scheme 2. Synthesis of Triazole-Containing Derivatives with Acyclic Replacement of the Piperidine Ring of 3aa.

Scheme 2.

aSynthesis of intermediate 54 is in Scheme S1 (Supporting Information). Reagents and conditions: (a) Pd(PPh3)4, K2CO3, DMF, 85 °C, 5 h, and 27–55%; (b) PdCl2(dppf), dimethoxyethane/Na2CO3 (aq, 2 M) = 10:1, 60 °C, 4 h, and 73%; (c) 3-(4-bromophenyl)propanenitrile, Pd(PPh3)4, K2CO3, DMF/H2O = 1:1, 90 °C, 12 h, and 64%; (d) KOH, MeOH/H2O = 2:1, 50 °C, and 39–88%; and (e) TFA/THF = 2:1, rt, 0.5 h, and 62–98%.