Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-1H-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 89830-98-8, HPLC of Formula: C6H8N2

To a solution of 3-bromo-7,8-dihydro-6H-1,6-naphthyridin-5-one (0.100 g, 0.437mmol) and 4-cyclopropyl-1H-imidazole (0.0709 g, 0.65 5 mmol) in DMF (5.00 mL) is addedK2C03 (0.18 1 g, 1.31 mmol). The mixture is degassed with a stream of N2 for 5 minutes. DMEDA (0.0193 g, 0.218 mmol) and CuT (0.0832 g, 0.437 mmol) are added sequentially and the resulting mixture is stirred at 110 C for 16 hours under N2. The mixture is extracted with EtOAc (2x75mL) and washed with saturated brine (3 x25 mL). The organic extracts aredried over Na2SO4, filtered, and evaporated to dryness. The crude product is purified by silica gel flash chromatography, eluting with a gradient of 0% to 5% MeOH in DCM to give the title compound (0.060 g, 48.6%) as a light green solid. ES/MS (m/z): 255.0 (M+H), ?H NMR (400 IVIHz, CDC13) 8.74 (d, J=3.2 Hz, 1H), 8.33 (d, J=2.4 Hz, 1H), 7.81 (s, 1H), 7.10 (s, 1H), 6.31 (br s, 1H), 3.73 (dt, J=3.2, 6.8 Hz, 2H), 3.39 -3.15 (m, 2H), 1.99- 1.90 (m, 1H),0.96-0.88(m,4H)

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, 5-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD; LEI, Hui; LIU, Gang; TIAN, Yuan; ZHANG, Haizhen; (0 pag.)WO2018/160406; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 28890-99-5,Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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.

a) 20.0 g (78.8 mmol) 1 ,3-dibromo-5-fluoro-benzene, 16.3 g (78.8 mmol) 6H- benzimidazolo[1 ,2-a]benzimidazole and 43.5 g (0.315 mmol) potassium carbonate in 200 ml DMF are stirred for 17 h at 170 C. The reaction mixture is filtered hot and the precipitate from the mother liquor is filtered after cooling. The product is washed with water and ethanol and decocted with diethyl ether and ethanol. Yield 21.2 g (61 %).1 H NMR (400 MHz, THF-d8): delta 8.21-8.26 (m, 4H), 7.98-7.8.00 (m, 1 H), 7.68-7.73 (m, 2H), 7.31-7.49 (m, 4H).

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5BrN2

A solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.689 mmol) was added dropwise, over a 25 minutes period, to a solution of 5-bromo-1-methyl-1H-imidazole (4.1 g, 25.689 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.408 mmol, Intermediate 40: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and layers separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and precipitates filtered to provide the title compound as a tan solid.

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; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); 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. 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H10N2

The synthesis of 1-methyl-2-phenyl-1H-benzoimidazole (Mpb) is accomplished by referring to methods disclosed in Popov, 1. I., Chem. Heterocycl. Compd. (EN), 1996, 32, 6, p.672-681. The synthetic method is outlined in Scheme 1. To 20 mL acetone was added 2-phenyl-1H-benzoimidazole (1.94 g, 10 mmol), followed by the injection of iodomethane (1.42 mL, 12 mmol). The mixture was stirred at room temperature for 6 h, sodium hydroxide solution was then added, and the mixture reacted for an additional 5 min. The reaction mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using n-hexanes/EA (v/v=80/20) as eluent. After the product was completely isolated, 1.03 mg (0.49 mmol) of the title compound was obtained (49percent yield). 1H NMR (CDCl3, delta): 3.87 (s, 3 H), 7.32-7.41 (m, 3 H), 7.51-7.56 (m, 3 H), 7.83-7.86 (m, 3 H).

According to the analysis of related databases, 716-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheng, Chien-Hong; Chen, Ruey-Min; Guo, Hong-Ru; Chung, Jun-Wen; US2005/116626; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, HPLC of Formula: C19H13BrN2

The solution of n-BuLi in 2.5Mn-hexane (2.64 mL,6.6 mmol)was added dropwise to a solution of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d] imidazole (2.09 g, 6 mmol) in dry THF(30 mL) at 78 C. At temperature of 78 C, the resulting reactionmixture was stirred continuously. Thereafter, we slowly added trimethylchlorosilane(0.76 mL, 6 mmol) to the mixture. Then, thereaction temperature was allowed to warm at room temperatureand stirred overnight. The reaction was quenched by adding water, and the crude product was extracted twice using 100 mL ofdichloromethane. Finally, the crude productwaswashed with brine.The combined organic layer was dried over MgSO4 and subjected tofiltration. The filtrates were dried under reduced pressure, and theresidue was subjected to column chromatography using ethyl acetate/n-hexane (v:v 1:10) as an eluent. Compound 1 was obtainedas a white solid with yield of 78%. We could not perform train sublimationof compound 1 due to its poor thermal stability.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yi, Seungjun; Kim, Jin-Hyoung; Bae, Woo-Ri; Lee, Jiwon; Han, Won-Sik; Son, Ho-Jin; Kang, Sang Ook; Organic electronics; vol. 27; (2015); p. 126 – 132;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 26832-08-6, These common heterocyclic compound, 26832-08-6, name is 1H-Imidazole-4-carboxamide, 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.

D2O, H2O2 (30%), NaCl, NH4VO3 and ima were commercial products (Shanghai DingmiaoChemistry Co., Ltd) and used without purification. The ionic medium 0.15 mol L-1 NaCl/D2Osolution at 25 C was chosen to represent physiological conditions, in all solution NMR experiments.To form the ternary system of NH4VO3/H2O2/ima, NH4VO3 and H2O2 were first mixedin a 1:5 molar ratio in D2O to produce the species [VO(O2)2(D2O)]-/[VO(O2)2(HOD)]- followedby the addition of ima. Unless otherwise stated, the total concentration of vanadate specieswas 0.1 mol L-1. The NMR samples were allowed to stand at least 4 h to let the coordinationreactions reach equilibrium.The bisperoxovanadium crystals of 1 were prepared by adding 10 mL of H2O2 (30%, w/v,solution) and 1.17 g NH4VO3 to 50 mL distilled water. After NH4VO3 was dissolved, 1.11 g imawas added to the mixture. The mixture was stirred in an ice bath at 273 K for 0.5 h. The reactionmixture was then filtered and the solution was kept at 278-283 K for one week tocrystallize. The crystals were recovered by filtration and washed with 3 mL of cold water and5 mL of cold ethanol and then dried on a filter paper. Yield: ca. 50-70% (based on NH4VO3).

The synthetic route of 26832-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Shaowei; Xia, Wen; Yang, Yueyue; Yu, Xianyong; Li, Xiaofang; Journal of Coordination Chemistry; vol. 70; 17; (2017); p. 2958 – 2968;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

5465-29-2, name is 2-Propylbenzimidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 5465-29-2

[step 2] (Z)-2-(2-Hydroxymethyl-5,11-dihydrobenzooxepino[3,4-b]pyridine)propiononitrile (0.111 g, 0.396 mmol) obtained in step 1 was dissolved in THF (2 mL), 2,6-lutidine (0.276 mL, 2.37 mmol), lithium bromide (0.206 g, 2.37 mmol) and methanesulfonic anhydride (0.172 g, 0.989 mmol) were added and the mixture was stirred at room temperature for 16 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. 2-Propylbenzimidazole (0.053 g, 0.333 mmol) was dissolved in DMF (2 mL), potassium carbonate (0.218 g, 1.58 mmol) was added and the mixture was stirred for 15 min. To this mixture was added the residue obtained above, and the mixture was stirred at 60C for 2 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated Under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to give (Z)-2-[2-(2-propylbenzimidazol-1-yl)methyl-5,11-dihydrobenzooxepino[3,4-b]pyridine]propiononitrile (0.094 g, 56%).

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2327690; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 496-46-8, 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. 496-46-8 name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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.

10 mol of glycoluril (Sigma-Aldrich) was diluted in propylene glycol monomethyl ether acetate. While the solution was maintained at 50 C., a solution obtained by diluting 40 mol of glycidyl acrylate (Sigma-Aldrich) in the same solvent was slowly added thereto to allow the mixture to react. The obtained solution was separated through a column, and then the solvent was removed by using vacuum distillation, thereby obtaining a compound represented by [Formula 11]. The procedure was repeated to prepare a sufficient amount of the compound of [Formula 11]. (0093) (0094) The structure was confirmed through 1H-NMR. 5.80, 6.05, 6.43 (-CH=CH2), 3.43, 4.28, 4.43, 4.44 (aliphatic H), 2.0 (-OH)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; LG Chem, Ltd.; Lee, Keon Woo; Kwak, Sang Kyu; Lee, Changsoon; Kim, Hyehyeon; Kim, Saehee; US8828644; (2014); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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. Quality Control of 2-Isopropyl-1H-imidazole

General procedure: Compound 4 0.2 g (0.41 mmol) and 25 muL piperdine (0.82 mmol) was added to the 1.0 mL dried CH2Cl2.Anhydrous Na2CO3 20 mg was then added to the mixture, which was stirred for 12 h. The mixturewas washed with the distilled water, the organic phase was separated and dried over anhydrousNa2SO4, and then concentrated viarotary evaporation. The crude product was purified by silica gelchromatography with petroleum ether-acetone-strong ammonia water (v/v/v, 8/1/0.1) as the eluentto gain 0.18 g yellow solid compound 5a in 90% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36947-68-9, its application will become more common.

Reference:
Article; Feng, Xiu E.; Wang, Qin Jin; Gao, Jie; Ban, Shu Rong; Li, Qing Shan; Molecules; vol. 22; 12; (2017);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 137049-00-4,Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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.

To a solution of l-N-Boc-3-cyanoazetidine (5.0 g, 27.5 mmol) in 1,4- dioxane (50 mL) was added 4 N HCl (50 mL) and stirred for 2 h. The reaction was concentrated under vacuum. The residue was dissolved in CH2Cl2 (60 mL) and DIPEA (10.6 mL, 60.4 mmol) and added l-methylimidazole-4-sulfonyl chloride (4.94 g, 27.5 mmol) and stirred at room temperature for 20 h. The reaction mixture was washed with 2 N NaOH (50 mL), dried over MgSO4 and concentrated under vacuum to afford 8 as a white crystalline solid (4.97 g, 80%); ; Eta-nmr (300 MHz, CDCl3) delta 7.06 (s, IH), 7.56 (s, IH), 4.27-4.19 (m, 4H), 3.82 (s, 3H), 3.43-3.31 (m, IH); LC-MS (214) 99%, 0.93 min, m/z 227 ‘.1 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-4-sulfonyl chloride, its application will become more common.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; CONN, P., Jeffrey; WILLIAMS, Richard; JONES, Carrie, K.; SHEFFLER, Douglas, J.; WO2010/114907; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem