Imidazoles-derivatives

139481-44-0, name is Methyl 1-((2′-cyano-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, 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. 139481-44-0

Raw material (compound 2A) 20 g, in the reaction bottle, adding ethanol to 200 ml, triethylamine 5 g, 50% aqueous hydroxylamine solution 37 g, reaction 24h, the cooling crystallization, the white solid obtained 13.6 g (63.0%). HPLC detection reaction in the reaction solution at the end of the major amide impurity (compound 6A): product is 7.15% : 92.84% (that is, the impurity and the product of the ratio of 1 : 12.9), see Figure 2.

Statistics shows that 139481-44-0 is playing an increasingly important role. we look forward to future research findings about Methyl 1-((2′-cyano-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate.

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; China State Institute of Pharmaceutical Industry; Wang, Xiaomei; Sui, Qiang; Tang, Chao; Liu, Shuai; Ouyang, Qunxiang; Shi, Huilin; (17 pag.)CN103664792; (2016); B;,
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1792-40-1, A common compound: 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: 1/3-Butyl-2-methyl-5-nitro-1H/3H-benzimidazole was synthesized by previous reported method by the alkylation of 2-methyl-5-nitro-benzimidazole (0.05 mol) with butyl bromide (0.075 mol) in the presence of NaH (0.126 mol) in THF at room temperature for 8h. To a suspension of SnCl2.2H2O (135 mmol) in 2 N HCl (95.2 ml), 1/3-butyl-2-methyl-5-nitro-1H/3H-benzimidazole (36.4 mmol) was heated at 110 C for 7 h. After the completion of the reaction (monitored by TLC), the suspension was neutralized with 2 N NaOH and diluted with ethanol. Filtered the solid product and extracted the filtrate with chloroform, dried over Na2SO4, filtered and concentrated to get mixture of products which were separated through column chromatography using ethylacetate:methanol (9.5:0.5) to get pure solid compounds 2b and 2d.

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, 2-Methyl-5-nitro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sharma, Alka; Luxami, Vijay; Paul, Kamaldeep; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 414 – 422;,
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3034-50-2, Adding a certain compound to certain chemical reactions, such as: 3034-50-2, name is Imidazole-4-carbaldehyde, 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 3034-50-2.

12.0 g (124 mmol) 4-formyl-imidazole are placed together with 750 mg Raney nickel in 1000 ml of methanolic ammonia solution and shaken at 40¡ã C. for 30 min. Then the mixture is hydrogenated in a Parr apparatus under a hydrogen atmosphere at 5 bars pressure at 40¡ã C. for 14 h. Another 750 mg Raney nickel are then added and the mixture is again hydrogenated at 50¡ã C. under a hydrogen atmosphere at 5 bars pressure for 14 h. The mixture is filtered, evaporated down i. vac., and in each case methanol, toluene and ethanol are added to the residue and it is again evaporated down completely i. vac. The residue is combined with ethereal hydrochloric acid in methanol and evaporated down completely i. vac. The residue is in each case combined with methanol and dichloromethane and evaporated down completely i. vac.Yield: 21.2 g (quant.)Rt value: 0.49 min (D)C4H7N3*2 HCl (170.04/97.12)Mass spectrum: (M+H)+=98

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, Imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
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The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life. 71759-89-2

[0294] Sodium hydride (15.3 g, 385 mmol) was added to a mixture of 4-iodo-lH- imidazole (50 g, 257 mmol) in THF (150 mL) at 0 C. After stirring for 0.5 h, iodomethane (40.0 g, 282 mmol) was added to the solution and the resulting mixture was stirred at room temperature overnight under N2. TLC (DCM / EtOAc = 2/1, v/v) indicated that starting material was consumed and two new spots were formed. The reaction was quenched with MeOH (50 mL), then concentrated to dryness, the residue was purified by silica gel column (DCM / EtOAc = 10/1, v/v) to afford the desired product (higher Rf) (28 g, 52%) as a yellow solid. [0295] 1H NMR (400 MHz, CDCl3) d (ppm): 7.32 (s, 1H), 6.96 (d, 7= 1.2 Hz, 1H), 3.68 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 71759-89-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EPIZYME, INC.; HARVEY, Darren Martin; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; (246 pag.)WO2019/108824; (2019); A1;,
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68282-53-1, 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Example 20 (0253) (rac)-2,4-bis((jE)-2-(4-methyl-lH-imidazo-5-yl)vinyl)-6,7 0 i-tetrahydro- dipyrido[2,l- a:l’,2T-k][2,9]phenanthroHne-5,12-diium trifluoromethanesulfonate, HTA-C5-11Starting racemic helquat O (10.0 mg, 16.3 mupiiotaomicron), 1 -methyl- lH-pyrrole-2-carbaldehyde (57 mg, 522 mupiiotaomicron), pyrrolidine (22 mu, 261 mupiiotaomicron) and dry methanol (0.5 ml) were placed into a 10 ml flask and the resulting mixture was stirred under argon for 1 h at room temperature. Progress of the reaction was monitored by thin layer chromatography. The crude product was precipitated from the reaction mixture by addition of diethylether (5 ml). The suspension was centrifuged and the supernatant was separated from the solid pellet. The solids were dissolved in methanol (0.5 ml) and the pure product was precipitated by addition of diethylether (5 ml). The same procedure was repeated with tetrahydrofuran (0.5 ml) – diethylether (5 ml) and acetonitrile (0.3 ml) – diethylether (5 ml). Then, centrifugation of this suspension, removal of the supernatant and drying of the solid part under vacuum of an oil pump led to 10.1 mg (12.7 muiotaetaomicron, 78 % yield) of dark-yellow solid HTA-C5-1 1. (0255) (0256) NMR (400 MHz, acetonitrile-d3): 2.32 (s, 3H), 2.46 (s, 3H)5 3.12-3.43 (m, 4H), 4.27-4.31 (m, 1H), 4.80-4.88 (m, 2H), 5.05 (m, 1H), 7.01 (d, J= 16.04 Hz, 1H), 7.44-7.52 (m, 4H)} 7.62-7.76 (m, 4H), 7.83-7.96 (m, 2H), 8.13-8.17 (m, 1H), 8.026 (d, J= 1.96 Hz, 1H), 8.77 (dd, J= 2.12, 6.32 Hz, 1H), 10.38 (broad s, 2H for -NH).

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; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; VYSOKA SKOLA CHEMICKO-TECHNOLOGICKA V PRAZE; TEPLY, Filip; HAJEK, Miroslav; KUZMOVA, Erika; KOZAK, Jaroslav; KOMARKOVA, Veronika; HUBALKOVA, Pavla; REYES-GUTIERREZ, Paul Eduardo; JIRASEK, Michael; SONAWANE, Monoj R.; JOSHI, Vishwas D.; SEVERA, Lukas; NOVOTNA, Jana; WO2015/180701; (2015); A1;,
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Adding some certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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 1003-21-0. 1003-21-0

To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1.3 M in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C.) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C. in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 2: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C.) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C. with an ice bath and carefully quenched with 2 N aqueous HCl to pH=7, quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), phases split and the organic layer was washed with brine (2*200 mL), dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and suspension was filtered to provide the title compound as a solid.

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 5-Bromo-1-methyl-1H-imidazole.

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.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; US2015/105404; (2015); A1;,
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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. 3543-72-4, name is Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 3543-72-4

[0075] 163 g (559.5 mmol) of compound (5) were dissolved in 1875 g ethanol. 14 g of palladium catalyst on activatedcarbon doped with iron (5% Pd, 1% Fe) and an additional 0.8 g of iron(II) sulfate 7-hydrate or 0.8 g of iron(III) nitrate 9-hydrate were added. Compound (5) was then hydrogenated at a hydrogen pressure of up to 4 bar until completeconversion of the starting compound (5).[0076] The catalyst was removed by filtration, and the ethanolic solution concentrated until a dry product remained.This residue was crystallized from propan-2-ol or ethyl acetate.[0077] The yield of compound (6) was 128 g (489,8 mmol) with a content of > 99 % (87.5 % of theory).[0078] The overall yield of compound (6) was 80.4% of theory in relation to 2-fluoro-5-nitroaniline. In comparison, thesynthesis according to DD34727 starting from N-1-methyl-4-nitrobenzene-1,2-diamine (CAS 41939-61-1) is characterizedby a yield of 39.0%.

The synthetic route of 3543-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEYL Chemisch-Pharmazeutische Fabrik GmbH und Co. KG; Frey, Michael; Walther, Dirk-Detlef; EP2690096; (2014); A1;,
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2849-93-6, 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below.

The bispyridine ester amine compound (168 , 0.83 mmol) in Example 1 and benzoimidazole-2-carboxylic acid (190 , 1.17 mmol) were dissolved in DMF (5 ), HBTU (402 , 1.25 mmol) and triethylamine (0.58 , 4.17 mmol) were added to the solution, and the mixture was stirred at room temperature for 24 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a white solid (247 , 86 %) by chromatography (methanol : dichloromethane = 1:30).

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; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/125923; (2009); A2;,
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46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, 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. 46006-36-4

. [148] Into a 50-mL round-bottom flask, was placed lH-l,3-benzodiazole-4-carboxylic acid (42 mg, 0.26 mmol, 1.00 equiv), HATU (164 mg, 0.43 mmol, 1.50 equiv), DIEA (111 mg, 0.86 mmol, 3.00 equiv), 4,5,6,7-tetrahydro-2H-indazol-3-amine dihydrochloride (60.6 mg, 0.29 mmol, 1.10 equiv), N,N- dimethylformamide (5 mL). The resulting solution was stirred overnight at 25 C. The reaction mixture was diluted with DCM (50 mL), washed with H2O (50 mL x 3) and brine (50 mL x 3) and dried with Na2SC>4. After filtration, the filtrate was concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (Analyse HPLC-SHIMADZU): Column: XBridge Shield RP18 OBD Column, 5um, 19* 150mm; Mobile Phase A: water (0.1%FA), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 3% B to 20% B in 17 min; 254 nm. The collected fraction was lyophilized to give 18.5 mg (25%) of (3-amino-4,5,6,7-tetrahydroindazol-2-yl)(lH-benzo[d]imidazol-4-yl)methanone (Example 48) as an off-white solid. Rt= 15.5 min; MS (ES, m/z) [M+H]+: 282; 1HNMR (DMSO- 6, 400MHz, ppm): delta 11.57(s, 1H); 8.71(s, 1H); 8.02(d, J=7.6, 1H); 7.87(d, J=8.0, 1H); 7.47-7.43(m, 1H); 2.61-2.58(m, 2H); 2.45-2.46(m, 2H); 1.76-1.67(m, 4H).

Statistics shows that 46006-36-4 is playing an increasingly important role. we look forward to future research findings about 1H-Benzimidazole-7-carboxylic acid.

Reference:
Patent; THE ROCKEFELLER UNIVERSITY; PONDA, Manish, P.; BRESLOW, Jan, L.; SELNICK, Harold; EGBERTSON, Melissa; (207 pag.)WO2017/205296; (2017); A1;,
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33468-69-8, name is 4-(Trifluoromethyl)-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. 33468-69-8

Production Example 58 A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.18 g of 4-(trifluoromethyl)-1H-imidazole, 0,55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.40 g of 2-{3-[4-(trifluoromethyl)imidazole-1-yl]pyridin-4-yl}-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 57”). [Show Image] 1H-NMR (CDCl3) delta: 9.00 (d, J=5.2 Hz, 1H), 8,84 (s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8,06-8.04 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.70 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.52-7.50 (m, 1H)

Statistics shows that 33468-69-8 is playing an increasingly important role. we look forward to future research findings about 4-(Trifluoromethyl)-1H-imidazole.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2274983; (2011); A1;,
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