Imidazoles-derivatives

Application of 172499-76-2, 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. 172499-76-2 name is Ethyl 3-(1H-imidazol-2-yl)propanoate, 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.

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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-(1H-imidazol-2-yl)propanoate, and friends who are interested can also refer to it.

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

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. 51-17-2, name is 1H-Benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6N2

To a stirred solution of 1H-benzo[d]imidazole (2 g, 16.94 mmol) in acetic acid (25 mL) under an inert atmosphere was added 10% Pd/C (50% wet, 600 mg) at room temperature. The reaction mixture was stirred at 90-95 C. under a hydrogen atmosphere (75 PSI) for 24 h. After consumption of starting material (by TLC), the reaction mixture was filtered through a pad of celite and the pad was washed with EtOAc (100 mL). The filtrate was basified with saturated sodium bicarbonate solution (100 mL) and extracted with EtOAc (2*100 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain 4,5,6,7-tetrahydro-1H-benzo[d]imidazole (800 mg, 6.55 mmol, 40%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.52 (brs, 1H), 7.35 (s, 1H), 2.45 (brs, 4H), 1.74-1.67 (m, 4H)

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 51-17-2.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; (93 pag.)US2018/186773; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of mutilin (93g, 0.29 mole) in EtOAc (1 L) was cooled to -45 0C (CH3CN/dry ice bath) with mechanical stirring under nitrogen. Trifluoroacetyl imidazole (Aldrich, 5 x 1Og ampules, 5Og, 0.30 mole) was then added dropwise over 30-45 minutes. After stirring for 1 hour, TLC (10% EtOAc/hexanes) showed complete consumption of mutilin. The mixture was allowed to ward to – 200C, and was then washed with IN HCl (2 x 30OmL), water, brine and then was dried over magnesium sulfate and filtered. After concentration to 300-40OmL, IL of hexanes was added with stirring. The precipitated product was filtered and washed with hexanes (IL) to afford pure 11-OTFA-mutilin as a white crytalline solid (55g). Additional product was obtained by evaporating the filtrate, and stirring the residue in ethyl ether (10OmL), and diluting with hexanes (40OmL). Filtration and washing with hexanes gave a second crop (47g) which was ~90% pure by NMR.

The synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/62334; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C8H8N2O, 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. 1849-01-0.

To a solution of 1,3-dihydro-1,N-methyl-2-oxobenzimidazole (3.185 g, 21.5 mmol) in DMF (60 mL) is added NaH (60% in mineral oil,1.03 g, 25.78 mmol) portionwise at 0 C. After stirring at 0 C for 30 min.2,4-dichloropyrimidine (3.20 g, 21.5 mmol) is added, and the mixture is allowed to stir at 15 C for 12 hrs. The resulting mixture is quenched with water (200 mL) and the mixture is extracted with EtOAc (100 mL x 3), and washed with water (100 mL x 4), dried with Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (petroleum ether: EtOAc =10:1), to give 2-chloro-4-(1,3-dihydro-3,N-methyl-2-oxobenzimimidazol-1-yl)pyrimidine.

The synthetic route of 1-Methyl-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); 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. 54624-57-6, name is 2-Bromobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., 54624-57-6

Step 1. l-allyl-2-bromo-lH-benzo[d]imidazole [0724] A mixture of 2-bromo-lH-benzo[d] imidazole (0.400 g, 2.04 mmol), allyl bromide (0.35 mL, 4.08 mmol), 1,4-dioxane (15 mL), and 2 M aqueous sodium hydroxide solution (15 mL, 3.00 mmol) stirred for 2 h at 100 ¡ãC. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). The organic phase was separated and washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 20percent ethyl acetate/petroleum ether) to afford 1- allyl-2-bromo-lH-benzo[d]imidazole (0.251 g, 52percent) as a yellow oil. MS (ESI, pos. ion) m/z 237, 239 [M+H]+.

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; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

7098-07-9, name is 1-Ethyl-1H-imidazole, 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. 7098-07-9

(1) in the equipped with a stirrer,thermometer,Calcium chloride drying tube and dropping funnel500 ml four-necked flask6.10 g (0.05 mol) of 1,3-propanesultone and150 mL of ethyl acetate was added and the mixture was stirred1,3-propane sultone dissolved,The flask was heated in an oil bath equipped with methyl silicone oil70 ¡ã C,Slowly drop dissolved(0.065 mol) of N-ethylimidazole50 mL of ethyl acetate was added dropwise(Dropwise addition time: 30 min)Insulation reaction 2h,Pressure filtration,The residue was washed with ethyl acetate,Vacuum drying,To give 1- (3-sulfopropyl) -3-ethylimidazolium salt (EIm-PS)10.20 g,The yield was 93.6percent.

Statistics shows that 7098-07-9 is playing an increasingly important role. we look forward to future research findings about 1-Ethyl-1H-imidazole.

Reference:
Patent; Guangxi Kemao Forest Chemical Co., Ltd.; Jiangxi Jinan Forest Products Industrial Co., Ltd.; Guangdong Komo Co., Ltd.; Weng, Liang; Xu, Sheyang; Chen, Jiuji; (16 pag.)CN104926664; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4238-71-5, 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 4238-71-5 as follows.

To a cold (-50 0C) suspension of 1 -benzyl -IH- imidazole (1.58 g, 10.0 ramol) in anhydrous diethyl ether (50 mL) under nitrogen was added ?-butyl lithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) dropwise. After being stirred for 20 min at -50 0C, dry carbon dioxide (passed through Drierite) was bubbled into the reaction mixture for 10 min before it was allowed to warm up to 25 0C. 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 the precipitate gave a white solid which was suspended in methanol, treated with IN HCl/diethyl ether (4 mL) and concentrated in vacuo. Lyophilization of the residue from water (5 mL) afforded Cap-136 as a white solid (817 mg, 40%) . 1H NMR (300 MHz, DMSO~d6) 6 7.94 (d, J = 1.5 Hz, IH), 7.71 (d, J = 1.5 Hz, IH) , 7.50-7.31 (m, 5H),5.77 (s, 2H} ; Rt = 0.51 min (Cond. -MS-W5) ; 95% homogenity index; LRMS: Anal. CaIc. for [M+H] + CnH12N2O2: 203.08; found: 203.11.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; BACHAND, Carol; RUEDIGER, Edward H.; KADOW, John F.; WO2010/120621; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, 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. 2849-93-6

A mixture of 1H-benzimidazole-2-carboxylic acid (4.0g, 24.6mmol), aminoethanol (1.48mL, 24.6mmol), 1-hydroxybenzotriazole (4.14g, 27.1mmol) and N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (5.19g, 27.1mmol) in 80mL dimethylformamide was stirred for 12hat room temperature then concentrated in vacuo. The residue could be crystallized from ethanol (35mL). Yield: 3.13g (62%), EI-LRMS m/z 206.1= (M+H)+.

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 2849-93-6.

Reference:
Article; Szabo, Gyoergy; Kolok, Sandor; Orgovan, Zoltan; Vastag, Monika; Beni, Zoltan; Koti, Janos; Saghy, Katalin; Levay, Gyoergy I.; Greiner, Istvan; Keser?, Gyoergy M.; European Journal of Medicinal Chemistry; vol. 186; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 84946-20-3 name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, 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. 84946-20-3

EXAMPLE 20 To a stirred mixture of 3.5 parts of ethyl 4-hydroxy-1-piperidinecarboxylate and 135 parts of N,N-dimethylformamide was added 1 part of a sodium hydride dispersion 50% and stirring was continued for 2 hours at room temperature. After the addition of 5.2 parts of 2-chloro-1-[(4-fluorophenyl)methyl]-1H-benzimidazole, the whole was further stirred overnight at room temperature. The reaction mixture was poured into ice water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 2,2′-oxybispropane, yielding 2.5 parts (31.5%) of ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]oxy]-1-piperidinecarboxylate; mp. 94.0 C. (26).

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

Reference:
Patent; Janssen Pharmaceutica, N.V.; US4695575; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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 2Preparation of 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione 1-Trityl-1 H-imidazole-4-carboxaldehyde (12Og, 0.319mol) and phthalide (42.8g, 0.319mol) were added to stirred ethyl acetate (100OmL) in a 4-neck round bottom flask fitted with a mechanical stirrer, a thermometer, a dropping funnel and a reflux condenser.Meanwhile sodium methoxide (51.7g, 0.957mol) was added to cooled methanol (50OmL) in a separate vessel. Thereafter the methanolic solution of sodium methoxide was added to the reaction mixture at 6O0C and was heated at this temperature for 3 hours and then cooled to 3O0C, at which point the solvent was removed by distillation at a reduced pressure.The distillation residue was poured into water and aqueous hydrochloric acid solution was added, until pH=4-5. The solid orange-brownish precipitates were filtered, the crude product of 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione was washed on filter with water.After the recrystallization of crude 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione from ethanol the yield of the 2-(1-trityl-1 H-imidazole-4-yl)indan-1 ,3-dione intermediate product was 97.4g (67.2%), having a melting temperature of 213 to 215C

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

Reference:
Patent; Grindeks, a joint stock company; WO2009/71584; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem