Figure 4. Synthesis of aminobenzimidazoles 20–22.
Reagents and conditions: (a) i. Cl(CH2)2N(CH3)2·HCl, K2CO3, NaI, DMF, 60 °C, 15 h; ii. column chromatography (SiO2, EtOAc/MeOH 98:2), 23: 33%, 24: 30%; (b) H2, 10% Pd(C), MeOH, rt, 15 h, quantitative; (c) H2N(CH2)2N(CH3)2, K2CO3, DMF, 90 °C, 12 h, 60–78%; (d) HCOOH, H2O, reflux, 3 h, 92%; (e) 10% Pd(C), HCOOH, MeOH, reflux, 20 h, 69%; (f) 4 M H2SO4, THF, 50 °C, 1 h, quantitative.
