Category: 57090-88-7

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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 57090-88-7

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 57090-88-7, name: 1H-Imidazole-4-carbonitrile

Example 1 Production of 1-(1H-imidazol-4-yl)-2-methyl-1-propanone A solution of 4-cyanoimidazole (42.7 g, 0.458 mol) in THF (500 ml) was added dropwise over 30 min to a solution (1.4 L, 1.47 mol, 3.2 equivalents) of 1.1 M isopropyl magnesium bromide in THF at 0 to 10°C under a nitrogen atmosphere. The mixture was stirred at 15 to 25°C for 3 h. Water (430 ml) and 10percent aqueous sulfuric acid solution (860 ml) were successively added dropwise, and the mixture was stirred at 30 min. A 30percent aqueous sodium hydroxide solution was added dropwise to adjust the pH to 8. After partitioning, the aqueous layer was extracted with ethyl acetate (300 ml * 2). The organic layer was combined, and the mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and concentrated under reduced pressure. The concentration residue was broken up with isopropyl ether (300 ml). The crystals were collected by filtration and washed with isopropyl ether. The crystals were dried in vacuo (40°C) to give 1-(1H-imidazol-4-yl)-2-methyl-1-propanone (51.9 g, yield 82percent). 1H-NMR (CDCl3): delta1.25(6H, d, J=6.9Hz), 3.36(1H, quint, J=6.9Hz), 7.81(1H, s), 7.87(1H, s)

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, 1H-Imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1193258; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 57090-88-7, A common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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.

To a soluiton of 1H-imidazole-4-carbonitrile (300 mg, 3.2 mmol) in THF (50 mL) was added LiA1H4 (365 mg, 9.6 mmol). After stirred at reflux overnight, the reaction mixture was quenched by H20 (2 mL). And the mixture was dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated in vacuum. The residue was used for next step without further purification.

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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. Recommanded Product: 1H-Imidazole-4-carbonitrile

(b) 4-acetyl-1H-imidazole 1.42 g (15.3 mmol) 4-cyano-1H-imidazole are combined with 11.2 ml (33.6 mmol) 3n ethereal methyl-magnesium-bromide solution with 25 ml THF in 75 ml THF at 10° C. with cooling in the ice bath and after removal of the ice bath the mixture is stirred for another 2.5 h at ambient temperature. After the addition of another 3.5 ml (10.5 mmol) 3n ethereal methyl-magnesium bromide solution and stirring for 15 min at ambient temperature, 45 ml of 1m sulphuric acid are added and the mixture is stirred for 30 min. After the addition of 20 ml of 10n sodium hydroxide solution the organic phase is separated off, the aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The combined organic phases are dried on magnesium sulphate and evaporated down i. vac. Yield: 48percent C5H6N2O (110.11) Mass spectrum: (M+H)+=111

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57090-88-7, its application will become more common.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, 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 57090-88-7 as follows.

a) 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile A flask charged with imidazole-4-carbonitrile (0.5 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30percent EtOAc/hexane to give 0.80 g (70percent) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H). found 224.1.

According to the analysis of related databases, 57090-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; Meegalla, Sanath K.; Rudolph, M. Jonathan; Wall, Mark J.; Wilson, Kenneth J.; Desjarlais, Renee L.; Manthey, Carl L.; Molloy, Christopher J.; US2008/51402; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, The chemical industry reduces the impact on the environment during synthesis 57090-88-7, name is 1H-Imidazole-4-carbonitrile, I believe this compound will play a more active role in future production and life.

Step A. 1-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-imidazole-4-carbonitrile 1H-imidazole-4-carbonitrile (300 mg, 3.22 mmol) and 5-(chloromethyl)-2-(trifluoromethyl)pyridine (662 mg, 3.385 mmol) were taken into anhydrous DMF (5 ml) and cooled to 0 C. Sodium hydride (150 mg, 3.7 mmol) was added to the solution portionwise and stirred at room temperature for 2 hours. The reaction was quenched with saturated ammonium chloride (10 ml) followed by evaporation of the solvent in vacuo. The residue was suspended in dichloromethane (20 ml) and water (20 ml). The aqueous layer was extracted further with dichloromethane (20 ml). The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to provide the crude product which was purified by column chromatography (SiO2) eluting with a gradient of heptanes to 100% ethyl acetate to provide the title product as a white solid (79 mg, 9.7% yield). 1 H NMR (300 MHz, CDCl3) delta H NMR (300 MHz, (m, 1H), 8.79-8.57 (m, 1H), 8.50-8.23 (m, 1H), 8.02-7.83 (m, 2H), 7.84-7.72 (m, 1H), 5.56 (s, 2H).

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, 1H-Imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Lauffer, David J.; Bemis, Guy; Boyd, Michael; Deininger, David; Deng, Hongbo; Dorsch, Warren; Gu, Wenxin; Hoover, Russell R.; Johnson, JR., Mac Arthur; Ledeboer, Mark Willem; Ledford, Brian; Maltais, Francois; Penney, Marina; Takemoto, Darin; Waal, Nathan D.; Weng, Tiansheng; (667 pag.)US2019/322673; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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.

Synthesis of 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (1.5 g, 79.78 mmol) in DMSO (15 mL) under an argon atmosphere were added potassium carbonate (4.4 g, 31.91 mmol) and 1H-imidazole-4-carbonitrile (890 mg, 9.57 mmol) at room temperature. The reaction mixture was stirred at 50° C. for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to obtain 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile (1.1 g, 56percent) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.86 (s, 1H), 8.67 (s, 1H), 8.47 (s, 1H), 4.11 (s, 3H); LCMS: 245.8 (M+1); (column; X-Select CSH C-18 (50*3.0 mm, 3.5 m); RT 2.96 min. 0.05percent aq TFA: ACN; 0.80 mL/min); TLC: 40percent EtOAc:hexane (Rf: 0.4).

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, 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. 57090-88-7 name is 1H-Imidazole-4-carbonitrile, 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 round bottom flask was added 1H-imidazole-4-carbonitrile (300 mg, 3.22 mmol), 2- bromopropane (794 mg, 6.44 mmol), and K2CO3 (890 mg, 6.44 mmol) in DMF (9 ml). The reactiom mixture was stirred at room temperature for 18 h. The reaction mixture was filtered. The solvent was concentrated in vacuo. The residue was purified by prepHPLC to afford 310 mg of 1-Isopropyl-lH-imidazole-4-carbonitrile TFA salt and 71 mg of 3- isopropyl-3H-imidazole-4-carbonitrile TFA salt region-isomer.1-Isopropyl-lH-irnidazole-4-carboriitrile TFA salt was dissolved in EtOAc, washed with sat. NaHCO3, brine, dried under anhy. Na2SO4, filtered and concentrated to afford 200 mg of 1-isopropyl-l/Mrnidazole-4-carbonitrile as a colorless oil, m/z 136.5 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, 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. 57090-88-7 name is 1H-Imidazole-4-carbonitrile, 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 round bottom flask was added 1H-imidazole-4-carbonitrile (300 mg, 3.22 mmol), 2- bromopropane (794 mg, 6.44 mmol), and K2CO3 (890 mg, 6.44 mmol) in DMF (9 ml). The reactiom mixture was stirred at room temperature for 18 h. The reaction mixture was filtered. The solvent was concentrated in vacuo. The residue was purified by prepHPLC to afford 310 mg of 1-Isopropyl-lH-imidazole-4-carbonitrile TFA salt and 71 mg of 3- isopropyl-3H-imidazole-4-carbonitrile TFA salt region-isomer.1-Isopropyl-lH-irnidazole-4-carboriitrile TFA salt was dissolved in EtOAc, washed with sat. NaHCO3, brine, dried under anhy. Na2SO4, filtered and concentrated to afford 200 mg of 1-isopropyl-l/Mrnidazole-4-carbonitrile as a colorless oil, m/z 136.5 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem