Electric Literature of 152628-02-9,Some common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Compound c, represented by Formula 3, was synthesized using Compound a and Compound b purified in Example 1-1. Lithium tert-butoxide was reacted in an inexpensive t-BuOH (tert-butyl alcohol) solvent to obtain compound c in a yield of 54%. As a result of comparing various base conditions such as pyridine, DMAP, Et3N, K2CO3, KOAc, NaOEt, NaH, and Na / MeOH, Compound c was obtained in a yield of 66% at a room temperature of Na / MeOH and 71% at 70 C. Also, a reaction of 1 g scale was carried out to synthesize compound c in the final 70% yield. Then, in order to hydrolyze the obtained compound c, hydrolysis optimum reaction conditions were searched under various acid or base conditions.The reaction was detected in the acid hydrolysis conditions of HCl / CH2Cl2 or H2SO4 / H2O, but the yield was not improved, and the hydrolysis reaction was carried out using the base conditions.The reaction was optimized using sodium hydroxide (NaOH) and THF, DMSO, toluene or H2O solvent, and 3N NaOH / THF at 100 was selected. As a result, telmisartan, a compound represented by the following formula (4), was obtained in a yield of 93%.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, its application will become more common.