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. Author manuscript; available in PMC: 2020 Feb 14.
Published in final edited form as: J Med Chem. 2019 Feb 5;62(3):1643–1656. doi: 10.1021/acs.jmedchem.8b01958

Scheme 2. Synthesis of 5–7a.

Scheme 2.

aReagents and conditions: (a) tert-butyl(piperazin-4-yl)carbamate, Cu powder, neat (for 55) or dry DMF (for 56), 120 °C, 64% for 55, 37% for 56; (b) tert-butyl(piperidin-4-yl)carbamate, K2CO3, dry DMSO, 100 °C, 91%; (c) 4N HCl in 1,4-dioxane, CH2Cl2, rt; (d) pyridine-3-isothiocyanate, iPr2NEt3, CH2Cl2, rt, 75% for 6, 94% for 7 (2 steps); (e) NaNO2, acetic acid, H2O, 0 °C to rt, 96% (2 steps); (f) Zn powder, MeOH/acetic acid, 0 °C to rt; (g) pyridine-3-isothiocyanate, iPr2NEt3, CH2Cl2, rt, 55% (2 steps).