Category: imidazoles-derivatives

Electric Literature of 95470-42-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 95470-42-1 as follows.

To a solution of ethyl vinylether (6.6 ml, 68.65 mmol) in methylene chloride (CH2Cl2, 20 ml) was added trifluoroacetic acid (3 mmolpercent) at 00C at which reaction was conducted for 5 min, followed by mixing with a solution of the compound (8 g, 34.33 mmol) of Preparation Example 1 in CH2Cl2OO ml) . Reaction at room temperature for 3 hrs was precedent to the addition of water to the reaction mixture which was then extracted twice with CH2Cl2 and washed with saturated brine . The extract was dried over magnesium sulfate (MgSO4) and filtered, followed by the vacuum concentration of the filtrate. The purification of the concentrate through silica gel column chromatography (hexene:ethylacetate=2 : 1) afforded the title compound as a colorless oil (9.8 g, 93percent).1H-NMROOO MHz, CDCl3) sigma 5.68(q, IH), 4.37 (q, 2H), 3.44-3.35(m, 2H), 2.71(s, 3H), 1.67 (d, 3H), 1.39(t, 3H), 1.20 (t, 3H) ;MS 304 (M+) .

According to the analysis of related databases, 95470-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/111794; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16681-56-4, name is 2-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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. HPLC of Formula: C3H3BrN2

In a 10 mL vial was combined N-(4-fluoro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (0.30 g, 0.65 mmol), 2-bromo-1H-imidazole (0.143 g, 0.97 mmol), and KOAc (0.159 g, 1.62 mmol) in dioxane (3 mL) to give a black suspension. Nitrogen gas was bubbled in for 20 min before Pd(PPh3)4 (0.075 g,0.06 mmol) was added. The reaction was heated under microwave at 130 C for 4h. After concentration under reduced pressure the residue was dissolved with DMSO (0.5 mL) and MeOH (1.5 mL), filtered and purified by Gilson HPLC (MeCN/0.1% TFA in water) to give the title compound (2 M HCl in Et2O was added) as the HCl salt (0.050 g, 19% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-56-4, its application will become more common.

Reference:
Article; Yang, Bin; Hird, Alexander W.; Bodnarchuk, Michael S.; Zheng, Xiaolan; Dakin, Les; Su, Qibin; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Brassil, Patrick; Redmond, Sean; John Russell, Daniel; Janetka, James W.; Bioorganic and Medicinal Chemistry; vol. 28; 2; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144690-33-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 144690-33-5 name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

188.0kg of tetrahydrofuran was added to a glass-lined reactor, 54.0kg 4- (1- hydroxy-1-methylethyl) -2-propyl-1- {4- [2- (trityl-tetrazol -5 – yl) phenyl] phenyl} methylimidazole-5-carboxylate, 92.0.0kg 4.0kg purified water and lithium hydroxide monohydrate.After complete addition, 20 stirred for 18 hours, once every 2 hours the reaction temperature recording, tracking and detection TLC starting material to substantially complete the reaction.After completion of the reaction, 240.0kg Ethyl acetate and sodium chloride solution (20.0 kg of sodium chloride was added to 180.0kg purified water, and dissolved with stirring), stirred for 10 minutes, allowed to stand for 20 minutes stratification.The organic phase was washed with sodium chloride solution (32.0 kg of sodium chloride was added to 288.0kg purified water, stirred and dissolved) Average washed twice, each wash was stirred for 10 minutes and allowed to stand for 20 minutes.The organic phase was collected, dried over anhydrous sodium sulfate and stirred for 4 hours.Filtered, and the filtrate was concentrated under reduced pressure to remove ethyl acetate (water bath temperature controlled at 45 ¡À 5 , the degree of vacuum at -0.1 ~ -0.06MPa), a solution 188.0kg N, N- dimethylformamide, is added 15.3kg anhydrous potassium carbonate, 2.7kg of potassium iodide was stirred at 20 ¡À 10 was slowly added 14.5kg 4- chloro-5-methyl-1,3-dioxol-2-one, addition was completed, heating, feed temperature control reaction was stirred for 2 hours at 40 ¡À 2 .After completion of the reaction, the material was cooled to 15 ¡À 5 rejection filter, and the filtrate was added to a solution of sodium chloride (338.0kg sodium chloride to 940.0kg purified water, and dissolved with stirring), the following -5 ~ 0 stirred for 4h, rejection was filtered, the filter cake was charged to an oven baking pan blast drying oven at a temperature of 40 ¡À 5 8 hours.To give 58.2kg of trityl olmesartan medoxomil, a yield of 96.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhong Zhaobo; Cheng Jinrong; He Shaojie; Tang Zhaocheng; (6 pag.)CN110396084; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 693-98-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 693-98-1 as follows.

PREPARATION 75 4,5-Diiodo-2-methylimidazole STR156 A solution of iodine monochloride (32.5 g) dissolved in dichloromethane (100 cm3) was added dropwise over 1.5 hours to a solution of 2-methylimidazole (8.2 g) and triethylamine (20. 2 g) in dichloromethane (200 cm3) at -70¡ã under nitrogen. The mixture was stirred for a further 30 minutes, warmed to -30¡ã, and then poured into water (200 cm3). The resulting precipitate was filtered off, dried and recrystallized from ethyl acetate-hexane to afford 4,5-diiodo-2-methylimidazole (18.5 g) which was characterised spectroscopically and used directly without further purification.

According to the analysis of related databases, 693-98-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US4728653; (1988); A;,
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. 693-98-1, name is 2-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H6N2

Add 1 mol of 2-methylimidazole to a 250 ml three-neck round bottom flask,1.2 mol of acrylonitrile and 150 ml of anhydrous methanol,Obtaining a mixture; under the protection of a nitrogen atmosphere,The above mixture was stirred and refluxed at 60 C for 14 hours.The reaction product was obtained; after the reaction was stopped, unreacted acrylonitrile and a solvent were removed by rotary evaporation, and the treated reaction product was vacuum dried at 60 C for 24 hours.A yellow transparent liquid is obtained which is 1-nitrileethyl-2-methylimidazole.The yield was 83%.

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:
Patent; Hebei University of Technology; Zhang Wenlin; Huo Yu; Zhao Yongqi; Lan Xiaoyan; Shi Ziwei; Sun Tengfei; Li Gongwei; Li Chunli; (13 pag.)CN108586348; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 87941-55-7, The chemical industry reduces the impact on the environment during synthesis 87941-55-7, name is 4-Bromo-1-trityl-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a single-necked flask was added 4-bromo-1-trityl-1H-imidazole (1.5 g, 3.9 mmol)Sodium carbonate (1.2 g, 11.7 mmol),2-formylbenzeneboronic acid (864 mg, 5.8 mmol) and DMF (10 ml)Water (2 ml), the reaction system was filled with nitrogen,Tetrakis (triphenylphosphine) palladium (242 mg, 0.195 mmol) was added under nitrogen,90 C for 16 h, add water,Ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate, the solvent was concentrated,Purification by column chromatography on silica gel afforded compound 8 (930 mg, yield 58%).

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, 4-Bromo-1-trityl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hinova Pharmaceuticals Inc.; Fan, Lei; Chen, Ke; Li, Xinghai; Chen, Yuanwei; (24 pag.)CN106256830; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4238-71-5, 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. 4238-71-5, name is 1-Benzyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[00238] To a cooled (-50 C) suspension of 1 -benzyl- lH-imidazole (1.58 g, 10.0 mmol) in anhydrous diethyl ether (50 mL) under nitrogen was added w-butyl lithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) dropwise. After being stirred for 20 min at -50 C, dry carbon dioxide (passed through Drierite) was bubbled into the reaction mixture for 10 min before it was allowed to warm up to 25 C. The heavy precipitate which formed on addition of carbon dioxide to the reaction mixture was filtered to yield a hygroscopic, white solid which was taken up in water (7 mL), acidified to pH = 3, cooled, and induced to crystallize with scratching. Filtration of this precipitate gave a white solid which was suspended in methanol, treated with INHCl/diethyl ether (4 mL) and concentrated in vacuo. Lyophilization of the residue from water (5 mL) afforded the HC1 salt of Cap- 136 as a white solid (817 mg, 40%). XH NMR (300 MHz, DMSO-d6) delta 7.94 (d, J= 1.5 Hz, 1H), 7.71 (d, J= 1.5 Hz, 1H), 7.50-7.31 (m, 5H), 5.77 (s, 2H); Rt = 0.51 min (Cond.-MS- W5); 95% homogenity index; LRMS: Anal. Calc. for [M+H C11H12 2O2: 203.08;found: 203.11.

The synthetic route of 1-Benzyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; ROMINE, Jeffrey, Lee; NGUYEN, Van, N.; WANG, Gan; LOPEZ, Omar, D.; ST. LAURENT, Denis, R.; CHEN, Qi; BENDER, John, A.; YANG, Zhong; HEWAWASAM, Piyasena; XU, Ningning; MEANWELL, Nicholas, A.; EASTER, John, A.; SU, Bao-Ning; SMITH, Michael, J.; WO2011/75439; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 861325-16-8 as follows. Formula: C5H7BrN2

(S)-(7-(Methylsulfonyl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indol-3-yl)boronic acid (30.0 mg, 0.0650 mmol) and 5-bromo-1,4-dimethyl-1H-imidazole (11.3 mg, 0.0650 mmol) were dissolved in 1.5 mL of dioxane and 0.5 mL of water. To this was added potassium carbonate (26.8 mg, 0.194 mmol) and PdCl2(dppf)-CH2Cl2 adduct (3.69 mg, 4.52 mumol), and the reaction mixture was degassed by bubbling in argon while sonicating for 5 min. The vial was capped and heated at 100 C. for 1 h. The crude material was purified via preparative LC/MS (Preparative HPLC Method 1) with the following modifications: Gradient 30-70% B over 20 min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 5.80 mg, and its estimated purity by LCMS analysis was 91%. Two analytical LC/MS injections were used to determine the final purity. Injection 1: LC/MS Method 3, HPLC RT=1.32 min. Injection 2: LC/MS Method 4, HPLC RT=2.32 min. 1H NMR (500 MHz, DMSO-d6) delta 8.58 (s, 1H), 8.45 (d, J=8.1 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.74 (s, 1H), 7.68 (d, J=7.7 Hz, 2H), 7.34 (t, J=7.5 Hz, 2H), 7.30-7.23 (m, 1H), 6.01 (d, J=11.0 Hz, 1H), 3.91-3.84 (m, 1H), 3.73 (d, J=8.1 Hz, 1H), 3.54-3.45 (m, 1H), 3.26 (t, J=11.7 Hz, 1H), 2.17 (s, 3H), 1.91 (s, 6H), 1.73 (br. s., 1H), 1.63 (d, J=8.8 Hz, 1H), 1.46-1.28 (m, 1H), 0.94 (d, J=11.7 Hz, 1H).

According to the analysis of related databases, 861325-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Norris, Derek J.; Delucca, George V.; Gavai, Ashvinikumar V.; Quesnelle, Claude A.; Gill, Patrice; O’Malley, Daniel; Vaccaro, Wayne; Lee, Francis Y.; DeBenedetto, Mikkel V.; Degnan, Andrew P.; Fang, Haiquan; Hill, Matthew D.; Huang, Hong; Schmitz, William D.; Starrett, JR., John E.; Han, Wen-Ching; Tokarski, John S.; Mandal, Sunil Kumar; (220 pag.)US2016/176864; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 144689-93-0, 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Imidazole 1 (2.0-8.0 g, 8.3-33.3 mmol), trityl protected tetrazolebiphenyl 2 (1.0 equivalent) and LiOH*H2O (1.0 equivalent) were stirred at ambient temperature in solvent-1 (17.5 mL/g of 1). The course of thereaction was monitored by HPLC. At partial conversion to the ester 3(when ca. 10 % of 2 was present in the reaction mixture), the temperature was raised to 40 C. When quantitative conversion to ester 3 was reached LiOH*H2O (1.5 equivalent) was added at 40 C to the reaction mixture and stirred at this temperature until the sufficient conversion to 4 was obtained. The reaction mixtures in entry 1-4 experiments were cooled to ambient temperature, in entry 5-6 experiments the temperature was maintained and reaction mixture stirred at 40 C until the reaction mixture contained less than 3% of 3. Then K2CO3 (1.1equivalent) was added followed by dropwise addition of 5 (1.23equivalent) solution in solvent-2 (2 mL/g of 1). The temperature of the reaction was raised to 50 C and mixture was stirred until quantitative conversion to 6 was obtained (if necessary, a smaller proportion of 5 was added). The reaction mixture was cooled and poured onto a mixture of ice and water, stirred for at least 0.5 h, the precipitate was filtered off and then re-slurred twice in water. The crude wet product was recrystallized from acetone and obtained precipitate was washed with a mixture of acetone/water (v/v=1/1).

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Toplak ?asar, Renata; ?asar, Zdenko; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4348 – 4359;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 641571-11-1, These common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 suspension of methyl 4-methyl-3-(4-(pyridin-3-yl)thiazol-2-ylamino)benzoate (325 mg, 1mmol) and 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (241 mg, 1 mmol) in 10 mL anhydrous THF was cooled to -20 C, a solution of tBuOK (672 mg, 6 mmol) in 10 mL anhydrous THF was added. The reaction mixture was warmed to room temperature slowly and stirred at r.t. for 10 h. The reaction was quenched by adding brine, extracted by E.A., the organic phase were combined, then remove the solvent and the residue was purified by column chromatography on silica gel to afford the title product as a white solid (459 mg, 86%).

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 641571-11-1.

Reference:
Article; Wang, Deping; Zhang, Zhang; Lu, Xiaoyun; Feng, Yubing; Luo, Kun; Gan, Jirong; Yingxue, Liu; Wan, Junting; Li, Xiang; Zhang, Fengxiang; Tu, Zhengchao; Cai, Qian; Ren, Xiaomei; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 21; 7; (2011); p. 1965 – 1968;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem