Tag: M.W=200-300

Electric Literature of 28890-99-5, 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 16 a) 7.00 g (24.7 mmol) 1-bromo-4-iodo-benzene, 10.5 g (32.2 mmol) caesium carbonate, 2.36 g (12.4 mmol) copper(I) iodide and 2.85 g (24.7 mmol) L-proline are added to 5.13 g (24.7 mmol) mmol) 5H-benzimidazo[1,2-a]benzimidazole in 80 ml DMSO under nitrogen. The reaction mixture is stirred for 15 h at 100 C. and 4 h at 150 C., filtered on Hyflo with dichloromethane. The organic phase is washed with water. The organic phase is dried with magnesium sulfate. The product is decocted with diethylether and methyl ethyl ketone (MEK). Yield: 2.90 g (77%).1H NMR (400 MHz, DMF-d7): delta 7.93-8.10 (m, 4H), 7.78-7.92 (m, 2H), 7.72-7.79 (m, 1H), 7.49-7.71 (m, 1H), 7.31-7.49 (m 4H). b) The product of Example 16b) is prepared in analogy to the procedure described in Example 4b).1H NMR (400 MHz, DMF-d7): delta=8.19-8.33 (m, 10H), 7.83-7.87 (m, 2H), 7.73-7.77 (m, 2H), 7.35-7.54 (m, 4H). One signal is covered by DMF MS (APCI(pos), m/z): 565 (M+1).

The synthetic route of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2012/241681; (2012); 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.

b) Compound 3-1 (1.55 g, 4.4 mmol), benzimidazolo[1,2-a]benzimidazole (960 mg, 4.6 mmol), and potassium phosphate (1.97 g, 9.3 mmol) were suspended in NMP (22 mL). The mixture was stirred at 190 Cfor 18.5 h. After the reaction mixture was cooled at roomtemperature, 44 mL of EtCH and 22 mL of water were added to the reaction mixture to give a solid. It was collected by filtration, and it was purifed by column chromatography on silica gel eluting with a mixed solvent of toluene and CHCI3.The product was further purified by recrystallization with toluene and cyclohexane to result in compound A-1O (yield: 1.55 g (65%)) as a white solid. LC-MS (mlz) 538.1HNMR (300 MHz, DMSO-c): 68.42-8.39 (m, 2H), 8.32-8.25 (m, 2H), 7.95-7.82 (m, 3H),7.72 (dd, J= 1.2, 7.6 Hz, 1H), 7.61-7.58 (m, 1H), 7.50-7.32 (m, 9H), 7.25 (t, J= 7.9 Hz,1H), 7.20-7.17 (m, 2H), 6.38 (dd, J= 1.1, 8.0 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; NISHIMAE, Yuichi; KOHLSTEDT, Julia; SCHAeFER, Thomas; NAGASHIMA, Hideaki; (114 pag.)WO2016/97983; (2016); A1;,
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Imidazole | C3H4N2 – PubChem

Related Products of 86604-86-6, A common heterocyclic compound, 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, molecular formula is C8H4ClF3N2, 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.

Example 2 N-(5-(Trifluoromethyl)-1H-benzo[d]imidazol-2-yl)quinolin-8-amine A mixture of 2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole (66 mg, 0.3 mol, prepared according to the procedure described in WO 2004/035549 A1) and 8-aminoquinoline (29 mg, 0.6 mmol, Aldrich) in EtOH (2 mL) was subjected to microwave irradiation at 170 C. with stirring for 30 min. The reaction mixture was allowed to cool to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel chromatography eluding with 3% MeOH/DCM to give the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 329 (M+1).

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; Norman, Mark H.; Ognyanov, Vassil I.; Wang, Xianghong; US2006/160872; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 641571-11-1, category: imidazoles-derivatives

To a solution of 13 (100 mg, 0.33 mmol) in NMP (2 mL) was added SOd2 (58 mg, 0.49 mmol). The reaction was heated at 90 C for 1 hour before 3 (80 mg, 0.33 mmol) was added. The resulting mixture was stirred at 90 C for 3 hours. The reaction was quenched with water and basified with aqueous NaOH. The mixture was extracted with EtOAc twice. The combined organic layers were washed with brine, dried overNa2SO4 and concentrated. The residue was purified by reverse prep-HPLC and then silica gel prep-TLC to give 4-methyl-N-(3-(4-methyl-1 H-imidazol-1 -yl)-5- (trifluoromethyl)phenyl)-3-((4-phenylpyrimidin-2-yl)amino)benzamide (22 mg, 13%) as a white solid.

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; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2963-77-1, These common heterocyclic compound, 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)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: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8).

The synthetic route of 2963-77-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; L’abbate, Fabrizio P.; Mueller, Ronel; Openshaw, Roxanne; Combrinck, Jill M.; de Villiers, Katherine A.; Hunter, Roger; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 243 – 254;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 1450-93-7, A common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), molecular formula is C6H12N6O4S, 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.

1.1. 7-(pyrimidin-4-yl)-1 H-imidazo[1,2-a]pyrimidin-5-one A mixture containing 2.9g (15 mmol) of 3-oxo-3-(pyrimidin-4-yl)-propionic acid ethyl ester (prepared by analogy to the method described in patent DE 2705582), 2g (15 mmol) of 2-aminoimidazole hemisulfate and 1.2g (15 mmol) of ammonium acetate was heated at 140?C during 18 h. The cooled mixture was treated with 30ml of acetonitrile and filtered and the precipitate was added to water and heated at reflux temperature for 30 min. The resulting solution was cooled and the precipitate recovered by filtration. The crude product thus obtained was recrystallised from ethanol to give 1.75g of pure product as a gray solid. Mp: 345-346?C

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; SANOFI-SYNTHELABO; MITSUBISHI PHARMA CORPORATION; EP1340759; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 13275-42-8, 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 13275-42-8 as follows.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuCl2 (7 mg, 0.05 mmol, 10 mol%), K3PO4 (212 mg, 1 mmol), 1,10-phenanthroline monohydrate (20 mg, 0.1 mmol, 20 mol%), 2-(2-bromophenyl)-1,4,5,6-tetrahydropyrimidine 1 or 2-(2-bromophenyl)- 1H-benzo[d]imidazole 4 (0.5 mmol), and N-heterocycle 2 (0.5 mmol). The Schlenk tube was evacuated and backfilled with O2 (this procedure was repeated three times). Under a counter flow of O2, DMF (2.0 mL) was added using a syringe. The reaction mixture was stirred at 110 C for 24 h. After the reaction was completed, the mixture was extracted with dichloromethane (3 ¡Á 15 mL), and then the organic layer was washed with brine (3 ¡Á 10 mL) and dried over anhydrous Na2SO4. Subsequently, the solvent was removed, and the product was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol as the eluent, affording the pure products.

According to the analysis of related databases, 13275-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Dingben; Huang, Ling; Yang, Jianguo; Ma, Junna; Zheng, Yingying; Luo, Yi; Shen, Yang; Wu, Jiashou; Feng, Chao; Lv, Xin; Tetrahedron Letters; vol. 59; 21; (2018); p. 2005 – 2009;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, 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 26576-46-5, Safety of 5-Acetoacetlamino benzimdazolone

This Comparative Example follows the conventional method described in German Patent No. 3140141. 2.0 g (0.0146 mol) of Anthranilic acid, 35 mL of deionized water, and 8.5 mL of 5 M hydrochloric acid are mixed with magnetic stirring while stirring in a 3-neck round bottom flask equipped with a thermometer. The clear solution is cooled to below 0C before adding dropwise a solution of 1.058 g NaNO2 (0.0153 mol) dissolved in 6 mL deionized water (about 2.5M NaNO2) at a rate that maintains an internal temperature below 0C. The diazo solution is kept stirring cold for at least 30 min. A second solution is prepared by mixing 3.47 g (0.0149 mol) of 5-acetoacetylamino-benzimidazolone (TCI America), with a basic solution containing 1.715 g (0.0429 mol) of NaOH dissolved in 10 mL deionized water. This second solution is then added to a third mixture containing 195 mL deionized water, 6 mL of glacial acetic acid (0.105 mol), and sodium hydroxide (2.29 g, 0.0573 mol), resulting in a finely suspended colloidal solution of white coupling component. The cold diazo solution is then added dropwise at room temperature to a vigorously stirred suspension of the coupling component, producing a yellow pigment slurry. The yellow mixture is stirred for at least 6 hours to complete the color development, after which time the slurry is filtered under vacuum through Versapor 0.8 mum filter membrane (PALL Corp.). The pigment wetcake is reslurried into 200 mL deionized water and then is vacuum filtered twice more, after which time the pigment wetcake is freeze-dried for 48 hours. The final product is a dark yellow powder (4.96 g, 89% yield), and after analysis by TEM imaging, consists of large aggregates and agglomerates of elongated rod-shaped particles having average lengths ranging from about 200 to about 500 nm.

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; Xerox Corporation; National Research Council of Canada; EP2290012; (2011); A2;,
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 40197-20-4 as follows. Application In Synthesis of 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid

Preparation Example 1 N-[3-(dimethylamino)propyl]-N’-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg), and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring at room temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure. The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. The mixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collected by filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

According to the analysis of related databases, 40197-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; (31 pag.)EP3231426; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 40644-16-4, name is 4-Bromo-1H-benzo[d]imidazol-2(3H)-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. COA of Formula: C7H5BrN2O

Step 3: To a solution of 4-bromo-1 ,3-dihydro-benzoimidazol-2-one (701 mg, 3.29 mmol) in DMSO (2 ml.) was added potassium acetate (803 g, 10.9 mmol), 1 ,1 ‘-bis(diphenyl phosphino)ferrocene palladium chloride (134 mg, 0.16 mmol) and bis(pinacolato)diboron (1.67 g, 6.58 mmol), and the reaction was degassed and heated in a microwave reactor for 30 minutes at 150 C. The reaction mixture was then filtered through a pad of Celite, water (60 ml.) was added, and the mixture was extracted with ethyl acetate (3 x 30 ml_). The combined organic extracts were dried over sodium sulfate, filtered, and then concentrated in- vacuo to give 4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol-2- one, which was used in the next step without further purification.

The synthetic route of 4-Bromo-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2009/108838; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem