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. 2013 Dec 8;57(2):462–476. doi: 10.1021/jm401568s

Scheme 1. The Synthesis of Compounds 13 and 24–33.

Scheme 1

Reagents and conditions: (a) NH2NHAc, nBuOH, reflux (41%); (b) NH2NH2, THF; (c) R5CO2H, p-dioxane, reflux (32–42%); (d) Boc-glycine, THF, reflux (39%); (e) 35, Pd(PPh3)4, K2CO3, p-dioxane/H2O (29–80%); (f) HCl, EtOAc (100%); (g) 36, Pd(PPh3)4, K2CO3, p-dioxane/H2O (25%); (h) (i) 37, Pd(PPh3)4, K2CO3, p-dioxane/H2O, (ii) SnCl2, EtOH, reflux, (iii) PhSO2Cl, pyridine, THF (16% over 3 steps); (i) 39, Pd(PPh3)4, K2CO3, p-dioxane/H2O (35%); (j) (i) 38 or 40, Pd(PPh3)4, K2CO3, p-dioxane/H2O, (ii) KOH, MeOH (39–79% over 2 steps).