Category: 152628-02-9

Synthetic Route 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.

Example 4. 4′-[[4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]-2-biphenylcarboxylic acid (telmisartan) (4′-Methyl-2′-propyl-1H-benzimidazol-6′-yl)-1-methyl benzimidazole (3.0 g, 9.8 mmol), 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl methanesulfonate (3.12 g, 10 mmol), tetrahydrofuran (15 ml) and potassium carbonate (1.38 g, 10 mmol) are loaded into a round-bottom flask equipped with magnetic stirrer, condenser and under nitrogen atmosphere. The mixture is stirred at room temperature for 8 hours, then 10% hydrochloric acid is added to pH=2. THF is evaporated off, which causes precipitation of boronic acid.

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; Dipharma S.p.A.; EP1719766; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 152628-02-9, Formula: C19H20N4

l-Ethyl-2-[4′-(bromomethylphenyl)]benzoate (30.30 g, 85.5%) was dissolved in N1N- dimethylformamide (100 ml) at 2 + 20C and 4-methyl-6-(l -methyl- 1-benzimidazolyl)- 2-propyl-l-benzimidazole (25 g) at 2 +/- 20C was added to the above solution followed by sodium hydroxide (3.42 g). Thereafter, stirring was continued at 2 +/- 20C till the completion of the reaction. Methylene chloride (125 ml) was added to the above reaction mass followed by DM water (250 ml, 22 +/- 20C) at 2 +/- 20C. Stirring was continued at 22 +/- 20C for 15 min and the layers were separated and the aqueous layer was extracted with methylene chloride (25 ml) at 22 +/- 20C. The combined organic extract was washed with DM water (125 ml) at 22 +/- 20C and the organic layer was concentrated till the mass temperature reaches to 6O0C at atmospheric pressure. Ethanol (75 ml) was added to the concentrated mass (Contains Telmisartan ethyl ester) at 600C and the concentration was continued till the vapor temperature reaches to 820C. The concentrated mass was cooled to 45 + 5 and diluted with ethanol (100 ml) followed by aqueous sodium hydroxide (prepared by dissolving 10.87 g of sodium hydroxide in 25 ml of DM water) at 45 + 50C in 15 +/- 5 min was added and the contents were heated to reflux at 78 +/- I0C. Thereafter, stirring was continued at reflux temperature (78 +/- I0C) till completion of the reaction. The reaction mass was concentrated at atmospheric pressure till the mass temperature reaches to 80 +/- 20C and DM water (375 ml, 28 +/- 20C) was added to the residue followed by methylene chloride (50 ml) and stirred for 10 min at 22 + 20C. The layers were separated and methylene chloride (200 ml) was added to the aqueous layer at 22 + 20C and pH was adjusted to 4.1 +/- 0.1 with hydrochloric acid (-17 ml, 30%w/w) and stirring was continued for 10 min at 22 +/- 20C. The layers were separated and the organic layer was washed with DM water (50 ml) at 28 + 20C. The organic layer was diluted with LambdazetaN-dimethylformamide (125 ml) at 28 + 20C and seeded with Telmisaratn Form A. Thereafter, the solution was kept on standing at 28 +/- 20C for 30 min and Telmisartan Form A crystallizes out. The resulting slurry was concentrated at atmospheric pressure till the mass temperature reaches to 84 +/- 20C. The slurry was cooled to 2 +/- 20C and stirred for Ih at this temperature. The product was filtered and washed with pre-cooled N,iV-dimethylformamide (25 ml, 0 +/- 20C) followed by pre-cooled ethanol (50 ml, O0C) and dried to obtain Telmisartan (30 g ) was having more than 99.7 % of HPLC purity.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

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

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.

Add 2-n-propyl-4-methyl-6-( -methylbenzimidazol-2′-yl) benzimidazole 100 g in 1000ml of acetone and of potassium hydroxide 22.0 g with stirring at 20-25C. Then of 4-bromomethyl-2′-cyanobiphenyl 92g is added at 20-25 C. Monitor the reaction on thin layer chromatography, after the reaction is completed, cooled to 0 to 5.0 C. and stirred for another hour at this temperature. The material is filtered, washed with chilled acetone, then wash with water, and then dried in a air drying cupboard at 80 C. Yield: 141.50 g (87.73% of theory); melting point: 196 C.-197 C; HPLC: 99.50%. N-3 isomer: 0.16%.

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; INOGENT LABORATORIES PRIVATE LIMITED; RAY, Purna, Chandra; NIGAM, Satish; PANDEY, Anand, Kumar; PATIL, Premchand; REDDY, Jagan, Mohan; ORUGANTI, Nagaraju; WO2011/77444; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 2-cyano-4?-(2?-n-propyl-4?-methyl-6?-(1??-methylbenzimidazol-2??-yl)benzimidazol-1?-ylmethyl) biphenyl [0023] In a 2 litre reaction flask 500 ml of methyl isobutyl ketone was added followed by 100 gm of 2-n-propyl-4-methyl-6-(1?-methylbenzimidazol-2?-yl)benzimidazole. The reaction mass was stirred and a solution of 40 gm sodium hydroxide in 300 ml water was added. To this solution, 10 gm tetra butyl ammonium hydrogen sulphate and 80 gm of 4-chloromethyl-2?-cyanobiphenyl was added. The reaction mass was warmed to 80 C. and maintained for 4 hours at 80 to 85 C. [0024] The completion of the reaction was monitored by TLC using mobile phase chloroform: methanol (9:1). After completion of the reaction, the mass was cooled to 20 C., maintained 3 hours at 15 to 20 C. The product which precipitated out was filtered, washed with methyl isobutyl ketone, followed by water to yield 126 gm of 2-cyano-4?-(2?-n-propyl-4?-methyl-6?-(1??-methylbenzimidazol-2??-yl)benzimidazol-1?-ylmethyl) biphenyl, melting at 196-198 C. [0025] C 80.53%, H 5.70%, N 14.20%; m/z=496.64 1H NMR DMSO d6 400 Mhz: delta ppm 0.96-0.99 (t, 3H) 1.75-1.84 (m, 2H) 2.62 (s, 3H) 2.89-2.93 (t, 2H) 3.80 (s, 3H) 5.67 (s, 2H) 7.18-7.92 (m, 14H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amarnath, U; Suryakiran, U; US2015/197495; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole

To a 100 mL flask was added 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole1.0 g (3.3 mmol), N-methylpyrrolidone4 g of potassium tert-butoxide and 0.4 g (3.6 mmol) of potassium tert-And stirring was started with a magnetic stirrer.While cooling to below 10 C.,A solution of 1.2 g (3.5 mmol) of 4′-bromomethylbiphenyl-2-carboxylic acid tert-butyl ester dissolved in 4.1 g of N-methylpyrrolidone was added dropwise over 2 hours. After the dropwise addition, the mixture was stirred at an internal temperature of 0 to 10 C. for 2 hours. As a result of sampling the reaction solution and conducting liquid chromatography analysis, it was found that 2 – n – propyl – 4 – methyl – 6 – (1 ‘- methylbenzimidazol – 2 – yl) benzimidazole was not detected and 4’ – [[4- Methyl-6- (1-methyl-1 H-benzimidazol-2-yl) -2-propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl-2-carboxylic acid tert-butyl ester was 86.0% Area percentage) was generated.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 152628-02-9.

Reference:
Patent; DNP FINE CHEMICALS UTSUNOMIYA COMPANY LIMITED; MATSUMOTO, TAKAFUMI; IKEDA, SHIN; SUZUKI, YOSHINOBU; (12 pag.)JP5711888; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, A new synthetic method of this compound is introduced below., COA of Formula: C19H20N4

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 152628-02-9, These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, its 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.

General procedure: A solution of an appropriate benzimidazole (5.03mmol) and NaH (0.12g, 5.53mmol, 60%) in 100mL anhydrous THF was stirred for 30minat 50C. After cooling to rt, a mixture of an appropriate bromide (6.04mmol) in anhydrous THF (50mL) was added dropwise to the solution. The solution was stirred for 3hat 50C. Then the resulting mixture was poured into 30mL ice water, and extracted with ethyl acetate (50mL×3). The combined organic layer was dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by CC to give the product as white solid 4.1.7.3 [4-[[2-Propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole-1-yl]methyl]-1H-indol-1-yl](phenyl)methanone (12c) 12c was prepared by following the above general procedure. Yield: 91.9%. MP: 214-216 C. 1H NMR (400 MHz, CDCl3): delta 8.34 (d, 1H), 8.04 (s, 1H), 7.27-7.73 (m, 12H), 6.74 (d, 1H), 6.52 (d, 1H), 5.67 (s, 2H), 3.89 (s, 3H), 2.89 (t, 2H), 2.78 (s, 3H), 1.85 (m, 2H), 1.02 (t, 3H). MS (ESI): [M + H]+ calcd 538.3; found 538.3.

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C19H20N4

The compound of formula I (0.62 g, 1 eq) was added to acetonitrile (10 ml) and stirred well. KOH (0.14 g, 1.1 eq) was added slowly, stirred for about 10 minutes, The title compound of Example 10 was added (II, R = COOCH3) (0.5 g, 1 eq) was slowly added, and after stirring for 3-4 hours, TLC After the reaction was complete, 50% ethanol (30 mL) was added directly, The reaction was refluxed for 6 hours. After the TLC test reaction was complete, the organic solvent was recovered under reduced pressure, The remaining solution was added dropwise with hydrochloric acid (1: 1) to pH neutral. There are solid precipitation, filtration, washing, extraction of telmisartan crude, Recrystallization of telmisartan (yield 75.1%), liquid purity greater than 98%.

According to the analysis of related databases, 152628-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Specialization Pharmaceutical Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Wu Mingjun; Li Jianfeng; Chen Weiming; Tian Guanghui; Zhu Fuqiang; Suo Jin; Shen Jingshan; (14 pag.)CN104768936; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, its 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. SDS of cas: 152628-02-9

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-02-9, These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, its 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.

Under the stream of nitrogen, the 4-methyl-6-(1-methyl-1H- benzimidazole-2-yl)-2-propyl-1H-benzimidazole of 50g was added to and stirred in isopropanol of 150ml and dimethyl sulfoxide of 50ml and potassium t-butoxide of 20.28g were added thereto, slowly heated, and stirred at 40~45C for 1 hour. The reaction mixture was cooled to 30~35C and the methyl 2-[4-(bromomethyl) phenyl] benzoate of 55.14g was added into the reaction mixture, which was stirred for 6 hours. The purified water of 250ml was added into the mixture and stirred at 20~25C for 1 hour. The resulting crystals were filtered and sequentially washed with purified water of 50ml and acetone of 50ml and dried to obtain the methyl 2-(4-{[4-methyl-6-(1-methyl-1H- benzimidazole-2-yl)-2-propyl-1H- benzimidazole-1-yl]methyl}phenyl)benzoate of 82.58g (yield of 95.1%).[88] m/e 528.6(parent ion); 1H NMR(DMSO-d6) delta0.99(t, 3H, J=7.24Hz), 1.73~1.88(m, 2H), 2.64(s, 3H), 2.92(t, 2H, J=7.42Hz), 3.50(s, 3H), 3.84(s, 3H), 5.64(s, 2H), 7.12~7.32(m, 6H), 7.33~7.82(m, 8H)

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONG WHA PHARM. CO., LTD.; OH, Yoon-Seok; LIM, Jae-Kyung; CHOI, Jung-Uk; KWON, O-Jin; LEE, Jun-Sang; WO2011/102645; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem