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. Author manuscript; available in PMC: 2017 Dec 22.
Published in final edited form as: J Med Chem. 2016 Dec 2;59(24):11148–11160. doi: 10.1021/acs.jmedchem.6b01450

Scheme 2.

Scheme 2

Synthetic routes to (A) pyridinyl analogs 2–4 (B) 5–10a

a Reagents and conditions: (a) bromoacetylbromide, DCM, rt, 3–12 h, 55%-95%; (b) 25, NaOEt, EtOH, reflux, 12 h, 32%-46%; (c) thiourea, n-BuOH, reflux, 3 h, quantitative; (d) Lawesson’s reagent, toluene, reflux, 4 h 30 min, 42%; (e) bromoacetyl bromide, DMAP, DCM, 0 °C to rt, 6–12 h, 62%-94%; (f) NaOEt, EtOH, reflux, 1 h, 23%-78%.