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. Author manuscript; available in PMC: 2020 Aug 21.
Published in final edited form as: J Med Chem. 2019 Jan 18;62(3):1484–1501. doi: 10.1021/acs.jmedchem.8b01656

Scheme 2. Synthesis of 13a1–6, 13b1–6, 13c1–6, and 13d1–6a.

Scheme 2.

aReagents and conditions: (i) 3,5-dimethyl-4-hydroxybenzonitrile, DMF, K2CO3, rt; (ii) N-(tert-butoxycarbonyl)-4-aminopiperidine, DMF, K2CO3, 120 °C; (iii) TFA, DCM, rt; (iv) substituted benzyl chloride (or bromide) or 4-picolyl chloride hydrochloride, DMF, K2CO3, rt.