Category: imidazoles-derivatives

Application of 3034-62-6, 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. 3034-62-6, name is 2-Iodo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The appropriate chloro-substrate (1 equiv) was dissolved in dioxane (0.04 M). Tripotassium phosphate (3.0 equiv), xantphos (0.05 equiv), palladium acetate (0.05 equiv) and the appropriate nucleophile (amine) (1.5 equiv) were then added. The reaction vessel was sealed and the mixture exposed to microwave radiation (150 0C, medium absorption setting) for 20 minutes. Upon completion the samples were filtered through a silica cartridge, washed with EtOAc and then concentrated in vacuo. The crude residue was then purified by preparative HPLC to give the desired products.

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-Iodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-21-0, 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. 1003-21-0 name is 5-Bromo-1-methyl-1H-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.

A mixture of a bromine substituted compound (1 eq.), boronic acid/boronate ester (1 eq.) in 1, 4-dioxane, and 2.5 eq. of 2M solution of potassium phosphate, was purged with Ar for 15 min, after which tetrakistriphenyl phosphine palladium (0.06 eq.) was added and the reaction stirred at 90 C overnight. After completion, the reaction mixture was filtered through Celite and evaporated to dryness. The residue was taken up in ethyl acetate, washed with water, followed by brine, then dried over anhydrous sodium sulfate and the solvent removed under reduced pressure. The crude product was purified by column chromatography or preparative HPLC to afford IV-9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ASSEMBLY BIOSCIENCES, INC.; WALKER, Michael; LI, Leping; HAYDAR, Simon, Nicolas; (95 pag.)WO2020/51319; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1H-Imidazole

Example 2; Comparative in Analogy to Example 1 from WO-A-00/14072 In a flask, 68.22 g of imidazole are suspended in 505 g of xylene. The mixture is heated to reflux and dewatered by taking off 5 g of a xylene/water mixture. The temperature is reduced to 66 C. and over the course of 30 minutes 25.2 g of phosgene are metered in with an introduction rate of 50.4 g/h. After about 15 minutes the reaction mixture takes on a consistency like that of chewing gum. When the metering of phosgene is at an end the imidazole hydrochloride by-product is in the form of yellow balls. After a further hour of stirring at this temperature, this temperature is raised to 130 C., and the consistency of the imidazole hydrochloride changes to a brown melt. The melt is drained off at 130 C. It solidifies on cooling to a dark-green, solid mass. The supernatant xylene phase is cooled to 0 C. The precipitated crystals are filtered off and dried at 20 mbar and 50 C. This gives carbonylbisimidazole in the form of white crystals with black fractions (Hazen colour number: 489). The purity is 96.8%, corresponding to a yield of 70% of theory.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Job, Andreas; Griehsel, Bernd; US2005/272937; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-15-4, These common heterocyclic compound, 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]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.

To a solution of 5-bromo-1-methyl-1H-benzo[dlimmdazole (1.0 g, 4.74 mmol) indioxane (10 mL) were added 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (1.5 g,5.68 mmol), sodium 2-ethylhexanoate (1.968 g, 11.86 mmol) and Pd(dppf)C12.DCM (247 mg,0.474 mmol) under N2. The mixture was stirred at 110 C for 4 h, poured into H20 (60 mL) andextracted with EA (50 mL x 2). The organic layers were dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and purified by silica gel column chromatography (PE/EA = 1/1) to afford 1 -methyl-S -(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-benzo[d]imidazole (1.0 g, 82 %) as a yellow solid. LC-MS m/z: 259.1 [M+Hf?. tR= 1.67 min.

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GOOD, Andrew, C.; (391 pag.)WO2017/176960; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4857-06-1, These common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]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.

To a solution of 2-chloro-1H-benzo[d]imidazole (3.0019 g, 19.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in 2.5 M sodium hydroxide solution (19.67 ml, 49.2 mmol, J. T. Baker) at 0 C. was added dimethyl sulfate (3.01 ml, 31.5 mmol, Riedel de Haen AG) dropwise. The reaction was allowed to stir for 1½ h. White precipitate was noted to form. The white precipitate was filtered, washed with water, and dried to give the title compound. LCMS showed product peak at 1.47 min (m+1=167.0). 1H NMR (400 MHz, DMSO-d6) delta ppm 3.80 (s, 3H) 7.21-7.28 (m, 1H) 7.28-7.35 (m, 1H) 7.59 (d, J=3.72 Hz, 1H) 7.61 (d, J=3.72 Hz, 1H)

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
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. 5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

1 ,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-dione (1 g, 3.8 mmol) in 2 ml of DM50 was dissolved. Then, 0.15 ml nitric acid (65%) and n-hexylalcohol (9.5 ml, 76.3 mmol) were added to the solution and the mixture was heated at 60 C. for 16 hours. After the reaction was over, the reaction liquid was cooled and iN NaOH was added around pH 7. Around 100 ml ethyl acetate was used to extract with mixture and the organic phase was washed by saturated NaC1(aq) solution for 2 times. After being dried by Na2SO4, the solvent was removed. The crude compound was purified by flash chromatography (Heptane/EtOAc). The product was obtained colorless viscous oil in 0.15 g, yield (%) ?H NMR (600 MHz, DMSO-d6): oe ppm) 5.50 (s, 2H), 4.73 (m, 8H), 3.36 (m, 8H), 1.46 (m, 8H), 1.24 (m, 26H), 0.85 (t, 12H)

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; Rohm and Haas Electronic Materials LLC; Rohm and Haas Electronic Materials Korea Ltd.; Grandbois, Matthew; Kim, Myung Yeol; Ryu, Eui Hyun; Sim, Jae Hwan; Jang, Min Kyung; Lee, Jung-June; (17 pag.)US2017/59991; (2017); A1;,
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. 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, A new synthetic method of this compound is introduced below., Safety of 5-Amino-1H-imidazole-4-carboxamide hydrochloride

AIL round-bottom flask (three neck) containing 340 g of trifluoroacetamide was heated in an oil bath at [110 C.] After the trifluoroacetamide melted, 50 g of 5- [AMINOIMIDAZOLE-4-CARBOXAMIDE-HCL] was added. The mixture was warmed to reflux (bath temp 160 to [165 C)] for 4 hours, cooled to room temperature, and the rocky solid was triturated with [1] L of ether. The ether was decanted off and the remaining solid was warmed until melted and 200 mL of ether was introduced by a dropping-funnel through a water-cooled condenser. The mixture was cooled to room temperature and an additional 200 mL of ether was added with stirring. The solid was removed by filtration, triturated with 3 x 500 mL of ether, washed with 200 mL of H20, and filtered to provide 89 g of crude product. The product was treated with 3 L [OF MEOH] and 9 g of activated carbon, warmed to reflux for 20 minutes, filtered through a pad of celite, and concentrated to a volume of 2.5 L. The material was warmed to dissolve all the precipitate that formed and then cooled slowly to room temperature. The crystalline material was isolated by filtration and dried in vacuo to provide 41 g of the desired hypoxanthine as a white solid. [‘H] NMR (DMSO-d6) [S] 8. 34 (s, 1H), 7.18 (bs, 2H). MS (ES+), 205.0 (100%, M + H).

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; MEMORY PHARMACEUTICALS CORPORATION; WO2004/14913; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10111-08-7, 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. 10111-08-7, name is Imidazole-2-carboxaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Potassium carbonate (0.863 g, 6.24 mmol) and 2-iodopropane (0.614 mL, 6.24 mmol) were added to a solution of 1H-imidazole-2-carbaldehyde (0.500 g, 5.20 mmol) in N,N-dimethyl formamide (5.2 mL) at room temperature. The reaction liquid was stirred at 60 C. for 4 hours. The reaction liquid was cooled to room temperature. Ethyl acetate and distilled water were added to the reaction liquid and the reaction liquid was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane/ethyl acetate) to obtain 1-isopropyl-1H-imidazole-2-carbaldehyde (0.355 g, 2.57 mmol, 49%) as a colorless oil. (0145) 1H-NMR (400 MHz, CDCl 3) delta: 1.48 (3H, d, J=6.4 Hz), 1.48 (3H, d, J=6.4 Hz), 5.48 (1H, quint, J=6.4 Hz), 7.30 (1H, s), 7.33 (1H, s), 9.83 (1H, s). (0146) ESI-MS: m/z=139 (M+H)+.

The synthetic route of Imidazole-2-carboxaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toray Industries, Inc.; Osada, Yuji; Izumimoto, Naoki; Morita, Yasuhiro; Udagawa, Shuji; Iseki, Katsuhiko; Miyoshi, Tomoya; Iwano, Shunsuke; (38 pag.)US2018/72701; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 760212-58-6, The chemical industry reduces the impact on the environment during synthesis 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

Fifth Step: Synthesis of Intermediate Product (E) (0135) 22.4 g (64.1 mmol) of the intermediate product (D), 19.6 g (77.0 mmol) of bis(pinacolato)diboron, 1.3 g (1.6 mmol) of [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (II), and 18.9 g (192.3 mmol) of potassium acetate were suspended in 230 mL of dimethylformamide and agitated at 80 C. for 12 hours. After cooling, the reaction solution was poured in distilled water to deposit a solid, which was filtered and separated. The filtered solid was recrystallized with ethyl acetate/hexane to provide 24.4 g (yield: 96%) of intermediate product (E).

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, 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHEIL INDUSTRIES, INC.; Jung, Ho-Kuk; Kang, Dong-Min; Kang, Myeong-Soon; Kang, Eui-Su; Kim, Nam-Soo; Lee, Nam-Heon; Chae, Mi-Young; (60 pag.)US9548460; (2017); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 28890-99-5, A common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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 4a) 7,78 g (25 mmol) 1-bromo-3-iodo-benzene, 16.3 g ( 50.0 mmol) caesium carbonate, 1 ,24 g (6.50 mmol) copper(l) iodide and 1 .50 g (13.0 mmol) L-proline are added to 5.18 g (25.0 mmol) mmol) 5 H-benzimidazo[1 ,2-a]benzimidazole in 1 00 ml dimethylsulfoxide (DMSO) under nitrogen. The reaction mixture is stirred for 18 h at 100 C. The reaction mixture is poured into water. The organic phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate. The solvent is distilled of. Column chroma- tography on silica gel with toluene gives the product. Yield 8.35 g (92%).1 H NMR (400 MHz, CDCI3): delta 8.25 (s, 1 H), 7.90-8.05 (m, 3H), 7.95-8.05 (m, 3H), 7.71 (d, J=7.9 Hz, 1 H), 7.65 (d, J= 7.9 Hz, 1 H). 7.50-7.65 (m, 2H), 7.26-7.45 (m, 4H).

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; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem