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Synthesis of second generation compounds 11a–c. Reagents and conditions: (a) 4-picolylamine, HATU, TEA, DCM, r.t., 5 h.; (b) CH3SO2Cl, Py, 40 °C, 2 h; (c) NH2OH·HCl, K2CO3, EtOH, r.t., 1 h.; (d) HCl 4 M in dioxane, r.t., 1 h.; (e) SOCl2, MeOH, r.t., overnight; (f) Boc2O, TEA, DCM, r.t., 1.5 h.; (g) LiOH, THF/H2O 4:1, r.t., overnight; (h) KOCN, HCl, 70 °C, 1 h.; (i) Ac2O, NaOH, H2O, r.t., 3 h.
