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. Author manuscript; available in PMC: 2022 Aug 12.
Published in final edited form as: J Med Chem. 2021 Aug 3;64(15):11729–11745. doi: 10.1021/acs.jmedchem.1c01136

Scheme 1. Synthesis of Piperazine and Diazepine “N-linked” Analogs.

Scheme 1.

Reagents and conditions: (a) DIEA, EtOH, 100 °C, 2h, 80-88%; (b) DIEA, NMP, 120 °C, 8h, 80-88%; (c) 4M HCl in dioxane, 2h, 89-98%; (d) EDCI/HOBt or HBTU, DIEA, 3,4-Cl2Ph(CH2)nCO2H, DMF, 30-85%; (e) DIEA, 3,4-dichlorobenzylsulfonyl chloride, DMF, 15%; (f) DIEA, 3,4-dichloroisocyanate, DMF, 10-45%; (g) NaH, THF, CH3I, 0 °C to rt, 22%.