Synthetic pathway for compounds 18, 20 and 21a,b.
Reagents and conditions:
EDC.HCl, HOBt, INH, DIPEA, DMF, 50 °C, 18 h, 64%; (b) CDl, NH2NH2H2O, DMF, rt, 16 h, 74%; (c) EDC.HCl, HOBt, POA, DIPEA, DMF, 50 °C, 18 h, 32%; (d) EDC.HCl, DMAP, POA, THF, DCM, rt, 72 h, 70%; (e) EDC.HCl, DMAP, INH, THF, DCM, rt, 72 h, 66%; (f) EDC.HCl, HOBt, benzohydrazide, DIPEA, DMF, 50 °C, 18 h, 41%.