Month: August 2021

Application of 25676-75-9,Some common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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 39 N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-1 -(1 -methyl-1 H- imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide (E39) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); To a stirred mixture of N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4- imidazolidinecarboxamide (100 mg, 0.33 mmol) (prepared as described in Example 28), 4-bromo-1 -methyl-1 H-imidazole (63.8 mg, 0.396 mmol) in 1 ,4-dioxane (6 ml) was added potassium phosphate (350 mg, 1.65 mmol), copper (I) iodide (62.8 mg, 0.33 mmol) and trans-N,N-dimethylcyclohexane-1 ,2-diamine (0.052 ml, 0.33 mmol) and the mixture was heated at reflux under argon for 1 h. The mixture was cooled to room temperature and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organic extracts were separated, washed with water and brine, dried and evaporated. The residue was purified by silca gel chromatography eluting with 0-20% methanol in dichloromethane, followed by mass- directed automated HPLC to give N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1- (1-methyl-1 H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide (15 mg, 12%). LC/MS [M+H]+ = 384 , retention time = 1.71 minutes.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, 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 172499-76-2, Computed Properties of C8H12N2O2

General procedure: A suspension of tBuOK (1.1 equiv. or 2.2 equiv.) and the imidazole derivative (1.0 equiv.) in DMF (6 mL/mmol) was stirred at rt for 1 h. The reaction mixture was treated with the corresponding alkyl bromide or alkyl mesylate (1.3 equiv. or 2.0 equiv.) and the temperature was raised up to 60 C and stirred at this temperature for 72 h. The solution was then diluted with EtOAc (20 mL/mmol) and washed three times with brine and H2O. The organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by CC.

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, Ethyl 3-(1H-imidazol-2-yl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kerscher-Hack, Silke; Renukappa-Gutke, Thejavathi; Hoefner, Georg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 852 – 880;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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 2466-76-4, Product Details of 2466-76-4

500.0 g (1.96 mol, 1.0 eq) of ganciclovir, 244.4 g (2.35 mol, 1.2 eq) of trimethyl borate, 7.5 kg of toluene were added to the reaction kettle, and heated to reflux for 5 hours.The TLC controlled raw material reacted completely, dropped to room temperature, and added triethylamine.396.7 g (3.93 mol, 2.0 eq), then added 3-acetylimidazole 323.7 g (2.94 mol, 1.5 eq), stirred at room temperature for 6 hours, HPLC controlled monoacetyl ganciclovir and N, O-diacetyl The ratio of Lovi is 94/4, the temperature is lowered to 0-10 ° C, 2.0 kg of methanol is added dropwise, and the mixture is stirred at room temperature for 2 hours. The solvent is concentrated under reduced pressure. 3.0 kg of ethyl acetate is added, and once with 500 g of water, the layers are separated. The aqueous layer was extracted with 500 g of ethyl acetate and the organic layers were combined.Concentration under reduced pressure, ethanol recrystallization to give colorless crystals 440.9 g, yield 75.7percent, purity 99.2percent,

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Anhui Haikang Pharmaceutical Co., Ltd.; Zhang Xiaoshun; (9 pag.)CN108409739; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-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. name: 5-Iodo-1H-imidazole

To a suspension of NaH (4.21 g, 105 mmol, 60%wt) in DMF (200 mL) at 0C was added 4-iodo-1H-imidazole (17 g, 88 mmol) in small portions. It was stirred for 1 h and SEM-Cl (16.07 g, 96 mmol) was added to the reaction. The mixture was stirred at rt for 12 h and poured into ice-water (200 mL). The mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were washed with water (3×50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluting with petroleum ether: EtOAc = 10:1 to 3:1 v/v) to afford the title compound. MS (ES+) m/z: 325 (M+H).

The synthetic route of 5-Iodo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., Quality Control of 1H-Imidazole

General procedure: To a stirred solution of phenylboronic acid (1.0 mmol), aniline (1.0 mmol), and K2CO3 (2.0 mmol) in deionized H2O (10 mL) at room temperature was added an aqueous suspension of FePd nanowires (3.0 mol % in 3 mL of H2O). The mixture was stirred at room temperature for 5h. After completion of the reaction (as monitored by TLC), 2 M HCl was added and the catalyst was separated by applying an external magnet. The catalyst was washed with EtOAc. The mixture was extracted with EtOAc (2 * 20 mL), dried, and concentrated. The residue was subjected to gel permeation chromatography to afford pure product.

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; Nasrollahzadeh, Mahmoud; Azarian, Abbas; Ehsani, Ali; Zahraei, Ali; Tetrahedron Letters; vol. 55; 17; (2014); p. 2813 – 2817;,
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. 7098-07-9, name is 1-Ethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H8N2

General procedure: As a general procedure for preparing Bronsted acidic ILs, the synthesis of 1-(4-butylsulfonic)-3-ethylimidazolium hydrogensulfate ([EImC4SO3H][HSO4]) is given as an example. To 1-ethylimidazole (10 g, 0.104 mol) in 50 mL of toluene, 1,4-butanesultone (14.2 g, 0.104 mol) dissolved in 50 mL of toluene was added dropwise under a dry nitrogen gas atmosphere. The resulting solution was refluxed with stirring at 60 °C for 24 h.After removing toluene, the product was washed thrice with 100 mL of diethyl ether to yield 1-(4-butylsulfonate)-3-ethylimidazol([EImC4SO3]) as a white powder. After dissolving [EImC4SO3] (20 g, 8.6102 mol) in 50 mL of methanol, sulfuric acid (0.84 g, 8.6102 mol) was added dropwise in an ice bath. The resulting solution was refluxed with stirring at 60 °C for 24 h. Following the reaction, methanol was removed by evaporation and then under reduced pressure, giving1-(4-butylsulfonic)-3-ethylimidazolium hydrogen sulfate ([EImC4SO3H][HSO4]) as a viscous liquid.

According to the analysis of related databases, 7098-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kakibe, Takeshi; Nakamura, Satoshi; Amakuni, Kiyokazu; Kishi, Hajime; Australian Journal of Chemistry; vol. 72; 2; (2019); p. 101 – 105;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

step 1.Take a 100ml single-mouth bottle and add 300mg 2-formylbenzeneboronic acid.1090 mg 1-trityl-4-iodoimidazole, 848 mg K3PO4,23mg Pd(PPh3)4, and 2ml water, 10ml DMF,Reacting at 100 C under N2 protection overnight,Complete reactionThe mixture was poured into water, and the mixture was extracted with EtOAc.Column chromatography gave 650 mg of light gray compound 26;

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 96797-15-8.

Reference:
Patent; Nanjing Huawei Pharmaceutical Development Co., Ltd.; Zhang Xiaoqing; Song Zhichun; Bao Jinyuan; (52 pag.)CN108689958; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate

Example-1 Preparation of Ethyl 4-{5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (III) Ethyl 4-[5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (II, 40.0 g, 0.153 mol) was added to 2-bromoethanol (80 mL) and agitated for 15-30 minutes. Acetonitrile (80 mL) and calcium carbonate (61.3 g, 0.61 mol) were added to the reaction mixture. The reaction mixture was heated to 80-90 C. within 2 hours and refluxed at 80-90 C. for 34-38 hours. The reaction mixture was cooled to below 70 C. and acetonitrile (80.0 mL) was added. The reaction mixture was further cooled to 20-30 C. and filtered through celite prewashed with acetonitrile. The filtrate was concentrated at 50-60 C. under vacuum till viscous mass is obtained. The viscous mass was cooled to 20-30 C. Dichloromethane (320.0 mL) was added to the viscous mass under stirring and washed with potassium carbonate solution (32.0 g in 200 mL water). The organic layer was washed with DM water twice. The organic layer (Dichloromethane) was concentrated under vacuum at 35-40 C. till viscous mass is attained. The viscous mass was dried under vacuum at 35-40 C. for one hour. Ethyl acetate (160.0 mL) was added to the viscous mass and cooled to 0-5 C. and stirred for one hour. The solid separated out was filtered and washed with ethyl acetate. The isolated solid was dissolved in dichloromethane and concentrated the solution under vacuum at 35-40 C. till viscous mass. The viscous mass was dissolved in acetone and cooled to 0-5 C. under stirring. The solid separated out was filtered, washed with acetone and dried at 40-45 C. under vacuum for 4-6 hours to give the title compound (III, 30.1 g; 56.30%), with a purity of 97.22%.

The synthetic route of 3543-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LIMITED; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; US2014/121383; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1219741-21-5, 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. 1219741-21-5, name is 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

K2CO3 (0.22 g, 1.61 mmol), followed by iodomethane (0.1 mL, 1.61 mmol), was added to a solution of 5-chloro-6-iodo- 1 ,3- dihydro-2H-benzimidazole-2-thione (I g, 3.22 mmol) in acetone (20 mL) at O0C. The reaction was stirred at rt for 1 h. Additional K2CO3 (1.61 mmol) and iodomethane (1.61 mmol) were added, and stirring continued at rt overnight. Volatiles were removed and the residue was partitioned between EtOAc and water. Concentration afforded the desired product as a white foam, which was used in the next step without further purification.

The synthetic route of 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 934-22-5,Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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 226:; 1 -(1 H-Benzoimidazol-5-yl)-4-(cyclopentylimino)-5-(1 H-indol-5-yl)- imidazolidin-2-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) and 1 H-lndole-5-carbaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours 2ml of a solution of KOCN (KSCN) (2mmol) and Pyridinehydrochloride (2mmol) in MeOH is added was added. Finally Isocyano-cyclopentane (1 mmol) is added. The reaction was stirred at room temperature for 48h. After evaporation of the solvent the residue was purified with chromatographic methods. Yield: 0.107 g (27 %); mp: 2100C, 1H-NMR (400 MHz, DMSO-D6): 1.20-1.25 (m, 1 H, CH2), 1.38-1.56 (m, 5 H, CH2), 1.70- 1.79 (m, 1 H, CH2), 1.82-1.90 (m, 1 H, CH2), 4.08-4.14 (m, 1 H, CH2-CH), 5.91 (s, 1 H, CH-N), 6.33-6.36 (m, 1 H, Ar), 6.85 (dd, 3J=8.3 Hz, 4J=1.7 Hz, 1 H, Ar), 7.24-7.33 (m, 4 H, 3 H Ar, 1 H Benzimid), 7.52 (s, 1 H, Benzimid), 7.63 (s, 1 H, Benzimid), 7.86 (m, 1 H, NH), 8.06 (s, 1 H, Benzimid), 11.05 (s, 1 H, NH), MS m/z 399.4 (M+H)+, HPLC (254 nm): rt 2.56 min (100 %), calc: C: 69.33, H: 5.57, N: 21.09, found.: C: 63.34, H: 6.16, N: 19.04 corresponds to C23H22N6O + 2.0 H2Omolecular weight (g/mol): 398.47 EPO RT – UV254nm (min): 2.56IC50 hQC (nM): 34.5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Aminobenzimidazole, its application will become more common.

Reference:
Patent; PROBIODRUG AG; WO2008/55947; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem