1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Adamantan-1-yl-{5-[2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-amine

Participants

Reaction Steps

Combine 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (100 mg, 0.310 mmol) and 1-isothiocyanato-adamantane (78 mg, 0.403 mmol) in DMF (2 mL) and heat to 70° C. for 1 hr. Add EDCI (119 mg, 0.620 mmol) and heat the reaction for 1 hr. Allow the reaction to cool to room temp and dilute with water (10 mL). Collect the resulting precipitate by filtration and purify the solid by reverse-phase HPLC (35-65% ACN/H2O+5 mM NH4OH) to afford the title compound as a white solid: 1H NMR (400 MHz, MeOD) δ ppm 1.74-1.82 (m, 6 H) 2.12 (s, 6 H) 2.15 (br. s., 3 H) 7.55-7.63 (m, 3 H) 7.76 (br. s., 1 H) 7.93 (br. s., 1 H) 8.18 (br. s., 1 H); MS (m/z) 480.1 (M+1).

Provenance & Evidence