Category: imidazoles-derivatives

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

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

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

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

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

Synthetic Route of 39513-26-3, These common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, 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.

5-bromo-1,3-dihydro-2H-benzo[d]imidazol-2-one (50 mg, 0.235 mmol), 20 (124 mg, 0.352 mmol), and Pd(PPh3)4 (14mg, 5 mol%), were combined in a microwave vial and flushed with N2 for5 min. Dioxane (3 mL) and aq. K3PO4 (1 M, 0.5 mL) wereadded and the mixture was heated in a Biotage microwave at 100 C for 1 h. H2O(3 mL) and EtOAc (7 mL) were added and the organic layer was separated, driedusing Na2SO4 and evaporated. Gilson HPLC purificationafforded 22 (1.44 mg, 2%).

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lotesta, Stephen D.; Marcus, Andrew P.; Zheng, Yajun; Leftheris, Katerina; Noto, Paul B.; Meng, Shi; Kandpal, Geeta; Chen, Guozhou; Zhou, Jing; McKeever, Brian; Bukhtiyarov, Yuri; Zhao, Yi; Lala, Deepak S.; Singh, Suresh B.; McGeehan, Gerard M.; Bioorganic and Medicinal Chemistry; vol. 24; 6; (2016); p. 1384 – 1391;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7098-07-9,Some common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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 generic experimental procedure is described: N-substituted imidazoles 1-6 (1 mmol equivalent) and 2,6-bis(chloromethyl)pyridine 7 (0.5mmol equivalent for each compound, m.p 73-78 °C; ALDRICH) were mixed together under inert condition in a 50 ml round bottom flask with gentle stirring. The temperature was then gently raised to 60 °C; giving a molten substance that was allowed to continue stirring for 16 h at 60 °C. The resultant grey or light brown crude solid was allowed to cool to room temperature and loaded onto a short plug of silica. Unreacted starting materials are rinsed-out with ethyl acetate while the salts were obtained (Rf value 0.01) as methanol (100percent) eluents. Solvent is then removed under reduced pressure to yield pure imidazolium salts 8-13.

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

Reference:
Article; Ibrahim, Halliru; Bala, Muhammad Dabai; Tetrahedron Letters; vol. 55; 46; (2014); p. 6351 – 6353;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13570-08-6, 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. 13570-08-6 name is 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, 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.

To a stirred solution of compound 80 (tosyiate) (536 mg, 1.36 mmol), compound 79 (200 mg, 1. 13 mmol) and HOBt (230 mg, 1.70 mmol) in 5 mL DCM, was added DIPEA (0.99 mL, 5.7 mmol) drop-wise and stirred at 0 C for 10 min under inert atmosphere. Then EDC-HC1 (283 mg, 1.48 mmol) was added to the reaction mixture and allowed to stir at room temperature for 16 h. After completion [confirmed by TLC (70% EtOAc-Hexane, Rf-0.4) and LC-MS] reaction mixture was partitioned between water (70 mL) and DCM (3×60 mL). Organic layer was separated, dried (MgSCfi) and concentrated. Resultant crude was purified by column chromatography (eluent: 30-65% EtOAc-hexane, S1O2) to yield compound 81 (210 mg, 48.8%) as white solid. Mass [ESI]: m/z. 379.45 [M++l]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; CYTOSITE BIOPHARMA INC.; BILCER, Geoffrey, Malcolm; KELLY, Terence, Alfred; (190 pag.)WO2019/160916; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 96797-15-8,Some common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, molecular formula is C22H17IN2, 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 suspensionof 4 (3.0 g, 6.9 mmol), the appropriate 2-formyl boronic acid(1.6 g, 10.7 mmol) and K3PO4 (4.4 g, 20.8 mmol) in DMF (30 mL) andwater (6 mL) was purged with nitrogen for 5 min, followed by theaddition of Pd(PPh3)4 (0.6 g, 0.5 mmol) and the mixturewas purgedwith nitrogen for another 5 min. The reaction mixture was stirredat 90 C for 16 h under an atmosphere of N2. The solution wasallowed to cool and was filtered through a plug of celite. Themixture was diluted with water (50 mL) and was extracted withethyl acetate to afford the crude product which was purified byflash column chromatography on silica gel to yield 6 as a white solid(1.9 g, 66.7%). Mp 147e149 C. 1H NMR (300 MHz, Chloroform-d)d(ppm) 7.97 (dd, J 7.8, 1.4 Hz, 1H), 7.72e7.54 (m, 3H), 7.38 (h,J 3.2 Hz,11H), 7.25e7.19 (m, 6H), 7.07 (d, J 1.3 Hz, 1H). MS (EI) m/z 415.2 [MH].

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

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Iodo-1-trityl-1H-imidazole

4-iodo-1-trityl-1H-imidazole (38.7 g, 88.8 mmol), (2-formylphenyl)boronic acid (20.0 g, 133 mmol)And K3PO4 (56.4 g, 266 mmol) was dissolved in 1,4-dioxane (300 mL) and water (60 mL).Nitrogen gas was bubbled through the reaction solution for 5 min, then Pd(PPh3)4 (5.12 g, 4.44 mmol) was added, and the reaction mixture was bubbled with nitrogen for 5 min.The reaction was heated at 90 C for 16 h under nitrogen.After the reaction was completed, the temperature was lowered, and the celite was filtered, and the filtrate was diluted with water (100 mL) and EA (300 mL), and the mixture was allowed to stand for separation. The aqueous phase was extracted with EA (300 mL×2; combined organic phase, water (100 mL) and saturated brine (100 mL × 3) washing.The organic phase was concentrated under reduced pressure to give a residue.Purified with PE/EA=3/1 column,Obtained a light brown viscous oil 2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (15.0 g, 40.8%).

The synthetic route of 96797-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Weixin Biological Technology Co., Ltd.; Yu Jindi; Lu Xianping; Li Zhibin; Xin Lijun; Zhu Jiangfei; Fu Chao; (67 pag.)CN108203438; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem