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. Author manuscript; available in PMC: 2018 Mar 15.
Published in final edited form as: Bioorg Med Chem Lett. 2017 Feb 13;27(6):1356–1359. doi: 10.1016/j.bmcl.2017.02.020

Scheme 2.

Scheme 2

Synthesis of M5 NAM analogs 9–11.a

aReagents and conditions: (a) nBuLi, THF, −78 °C, 2h, 50%; (b) ethylenediamine, pTsOH, 4Å sieves, toluene, 150°C μW 25 min, 70%; (c) 3,4-difluorobenzoyl chloride, DIPEA, DCM, 80%; (d) SFC, (CHIRALPAK IE, 20 mm × 250 mm column at 40 °C, back-pressure regulated at 100 bar, IPA cosolvent, 30% isocratic prep over 7 min at 80 mL/min).