Application 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.
l-Methyl-2-[4′-(bromomethylphenyl)]benzoate (148.68 g) was dissolved in N,N- dimethylformamide at 2 +/- 20C and 2-n-propyl-4-methyl-6-(r-methylbenzimidazol-2′-yl) benzimidazole (150 g) was added at 2 + 20C followed by sodium hydroxide (20.49 g). Thereafter, stirring was continued at 2 +/- 20C till completion of the reaction. Methylene chloride (750 ml) was added at 2 + 20C followed by DM water (150 ml, 22 +/- 20C) and stirring was continued at 22 +/- 20C for 15 min. The layers were separated and the aqueous layer was extracted with methylene chloride (150 ml) at 22 + 20C. The combined organic extract was washed with DM water (750 ml) at 22 +/- 20C and concentrated the organic layer (~ 1050 ml) till the mass temperature reaches to 54 +/- 20C at atmospheric pressure. Methanol (450 ml) was added to the concentrated mass at 53 +/- 20C. The concentration was continued till the vapor temperature reaches to 63 +/- 20C. The concentrated mass was cooled to 45 +/- 50C and diluted with methanol (600 ml). Aqueous sodium hydroxide (prepared by dissolving 65.22 g of sodium hydroxide in 150 ml DM water) was added at 45 +/- 50C in 15 +/- 5 min. The reaction mixture was heated to reflux at 68 +/- I0C. Thereafter, stirring was continued at reflux temperature (68 +/- I0C) till completion of the reaction. The reaction mass was concentrated at atmospheric pressure till the mass temperature reaches to 80 +/- 20C. DM water (2250 ml, 28 +/- 20C) was added to the residue followed by methylene chloride (300 ml) and stirred for 10 min at 22 + 20C. The aqueous layer was separated, methylene chloride (900 ml) was added to the aqueous layer at 22 + 20C and adjusted the pH to 4.1 +/- 0.1 with hydrochloric acid (-84 ml, 30% w/w) and stirred for 10 min at 22 +/- 20C. The aqueous layer was separated from methylene chloride (150 ml) at 22 + 20C. The organic layer was washed with DM water (300 ml) at 28 +/- 20C. The organic layer (-1200 ml) was diluted with JVjJV- dimethylformamide (750 ml) at 28 + 20C and seeded with Telmisartan Form A. The solution was kept standing for 30 mins and Telmisartan Form A crystallized out at 28 +/- 20C. The resulting slurry was concentrated at atmospheric pressure till the mass temperature reaches to 82 +/- 20C. The slurry was cooled to 2 +/- 20C and stirred for Ih at this temperature. The product was filtered and washed with pre-cooled DMF followed by pre-cooled ethanol to obtain Telmisartan (~275g-wet) having more than 99.7% HPLC purity.
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.
Reference:
Patent; AUROBINDO PHARMA LIMITED; KORRAPATI, Venkata Vara Prasada Rao; INTI, Venkata Subramanyeswara Rao; ANANTA, Rani; MEENAKSHISUNDERAM, Sivakumaran; WO2010/4385; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem