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. Author manuscript; available in PMC: 2010 Sep 1.
Published in final edited form as: Bioorg Med Chem Lett. 2009 Jul 18;19(17):4967–4970. doi: 10.1016/j.bmcl.2009.07.072

Scheme 3.

Scheme 3

Synthesis of the nitrile 7a, tetrazole 7b and thiadiazolone 7c. Reagents and conditions: (a) NH4OH, 88% (b) DIC, pyridine, carried on w/o purification (c) 3,5-dichloroaniline, EDC, HOBt, DMF, 60–73% (d) Bu3SnN3, toluene, μW, 30 min., 160 °C, 10%, (e) hydroxylamine·HCl, DMSO, DEA, (f) thiocarbonyl diimidazole, THF, rt 15% (two steps). DIC = N,N′-carbonyl diimidazole, DEA = diethylamine.