Category: imidazoles-derivatives

Synthetic Route of 25676-75-9, 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 25676-75-9 as follows.

Example 831 -Methylethyl [(2S,4/?)-1 -acetyl-2-methyl-6-(1 -methyl-1 H-imidazol-4-yl)-1 ,2,3,4- tetrahydro-4-quinolinyl]carbamate h drochlorideA mixture of 1 -methylethyl [(2S,4R)-1 -acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 ,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Intermediate 52) (150 mg, 0.36 mmol), 4-bromo-1 -methylimidazole (0.43 mmol), tetrakis(triphenylphosphine)palladium(0) (42 mg, 10 mol%) and potassium carbonate (199 mg, 1 .44 mmol) in toluene (2 mL) and ethanol (2 mL) was refluxed for 16 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt (10 mL) and water (10 mL) and the layers were separated. The organic phase was dried over MgS04 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM) gave a residue which was treated with 1 M HCI in Et20 (0.5 mL, slight excess). The solvent was evaporated and the residue triturated with Et20 to give 1 -methylethyl [(2S,4R)-1 -acetyl-2-methyl-6-(1 -methyl- 1 /-/-imidazol-4-yl)-1 ,2,3,4-tetrahydro-4-quinolinyl]carbamate hydrochloride (8 mg, 0.02 mmol, 5%) as a colourless solid. LCMS (method G): Retention time 0.56 min, [M+H]+ = 371.1

According to the analysis of related databases, 25676-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
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These common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, 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. Recommanded Product: 2-(1-Trityl-4-imidazolyl)benzaldehyde

Will (2-(2-phenylbenzofuran-5-yl)-2-oxoEthyl) dimethyl phosphate (0207-79) (254 mg, 0.738 mmol, 1.0 equiv),2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (305 mg, 0.738 mmol, 1.0 equiv) andCesium carbonate (480 mg, 1.476 mmol, 2.0 equiv)The isopropanol solution (10 ml) was stirred overnight at room temperature.After the reaction is completed, quench with water, dichlorineMethane extraction, the organic phase is washed with saturated brine,It was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a yellow oil.The resulting yellow oil was purified by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether = 1/2) to give the target product 1-(2-phenylbenzene)(Furan-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)propan-2-en-1-one (306 mg, Yield:65.7%) is a yellow oil.

The synthetic route of 2-(1-Trityl-4-imidazolyl)benzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, 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 16681-59-7, HPLC of Formula: C4H5BrN2

Similarly, compound f1 (6.05 g, 37.6 mmol)Dissolved in tetrahydrofuran (140 mL),Adding hexane solvent and dropping at -78 CAfter 2.5 M n-butyllithium (18 mL, 45.1 mmol),Stir for 1 hour.Then slowly add trimethyl borate (13 mL, 56.4 mmol)After that, stir for 2 hours.Then add 2M hydrochloric acid to neutralize,The product was extracted with ethyl acetate and water.Recrystallization from dichloromethane and hexane gave compound g1 (3.56 g, 77%).Weighed compound g1 (3.16 g, 25.1 mmol),Compound e1 (6.23 g, 25.1 mmol),Tetrakistriphenylphosphine palladium (11g, 10mmol)And potassium carbonate (8.42 g, 60.9 mmol),The weighed reactant was dissolved in toluene (1 L) / EtOH (200 mL) / distilled water (200 mL)The solvent was heated at 90 C for 2 hours.After the reaction is completed, the pressure is concentrated,Extract with ethyl acetate and concentrate.Column chromatography gave Intermediate A1 (4.07 g, 65%).

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; Changchun Hai Purunsi Technology Co., Ltd.; Han Chunxue; Cai Hui; (33 pag.)CN108676034; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 62366-53-4, 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 62366-53-4 as follows.

EXAMPLE 1 N-[1-(2-[1H-indol-3-yl]ethyl)piperidin-4-yl]-1-methyl-1H-imidazole-2-carboxamide A melt of 3-[2-(4-amino-1-piperidyl)ethyl]indole (1.0 g, 4.11 mmol), 2-hydroxypyridine (0.3 g, 3.16 mmol) and 2-methoxycarbonyl-1-methyl-1H-imidazole (0.57 g, 4.07 mmol) was heated at 160 C. for 3 hours under N2. More 2-methoxycarbonyl-1-methyl-1H-imidazole (5 drops) was added and heating continued for a further 11/2 hours. The mixture was cooled and chromatographed on silica (100-200 aktiv) eluding with absolute ethanol. The title compound was isolated as a brown glass (0.97 g,). This was dissolved in hot ethanol (ca. 10 cm3) and ethanolic HCl added to give an acidic solution from which the dihydrochloride of the title compound crystallized on cooling in ice, 0.48 g, m.p. 250-53 C. (on heating from cold sample gums 140-160 C., crystallises 225-40, starts to decompose at 245 then melts as above). Analysis: Found: C, 56.60; H, 6.23; N, 16.86% C20 H25 N5 0.2HCl requires: C, 56.61; H, 6.41; N, 16.50%.

According to the analysis of related databases, 62366-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; John Wyeth & Brother Limited; US4772617; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16042-25-4, These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic 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.

The synthesis of complex 2 was similarly to 1 except that H3PW12O40¡¤13H2O (0.22g, 0.07mmol) was used instead of H3PMo12O40¡¤26H2O. The pH value was adjusted to 1.8 with molL-1 HNO3 (final pH 2.17). Yellow block crystals were filtered and washed with distilled water (35% yield based on W). Elemental Anal. Calc. for C16H15Ag2N8O49PW12 (3556.09): C 5.39, H 0.42, N 3.15. Found: C 5.43, H 0.47, N 3.11%.

Statistics shows that 2-Imidazolecarboxylic acid is playing an increasingly important role. we look forward to future research findings about 16042-25-4.

Reference:
Article; Tian, Ai-Xiang; Hou, Xue; Ying, Jun; Liu, Guo-Cheng; Ning, Ya-Li; Li, Tian-Jiao; Wang, Xiu-Li; Inorganica Chimica Acta; vol. 439; (2016); p. 43 – 48;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 36947-69-0, 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. 36947-69-0 name is 2-(tert-Butyl)-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 microwave tube was charged with 2,6-dibromo-N-tert-butylpyridine-4-carboxamide (intermediate 1, step A) (0.84 g, 2.5 mmol), 2-(tert-butyl)-1H-imidazole (310 mg, 2.5 mmol), potassium phosphate (1.06 g, 5 mmol) and tetrabutylammoniumbromide (403 mg, 1.25 mmol), DMSO (5 ml) was added, the reaction mixture purged with argon for 5 mm in an ultrasonic bath, copper(I)iodide (47.6 mg, 250 tmol) and 4,7-dihydroxy-1,10-phenanthroline (106 mg, 500 tmol) were added, the tube was sealed and the reaction mixture was allowed to stir for 20h at 120C. The reaction mixture was cooled to room temperature, diluted with water (10 nil), and the precipitate collected by filtration. The crude product (950 mg) was purified by flash chromatography on silica gel [heptane/ ethyl acetate (20-80%)j to yield the title compound (494 mg, 52%) as an off-white solid, MS (ISN) mlz = 381.1 [(M+H)i, mp 216C.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HOENER, Marius; WICHMANN, Juergen; (65 pag.)WO2017/9274; (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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, A new synthetic method of this compound is introduced below., Safety of 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: A suspension of amine A1-A3 (1 mmol) in water is takenin a round bottomed flask; to this sulphonyl chloride(1 mmol) was added. This was stirred at room temperature while monitoring the reaction. The product was filtered,recrystallised using methanol-water and column purified.The structures were confirmed by 1H NMR, 13C NMR, IRand mass spectral analysis.

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; Vangala, Radhika; Sivan, Sree Kanth; Peddi, Saikiran Reddy; Manga, Vijjulatha; Journal of Computer-Aided Molecular Design; vol. 34; 1; (2020); p. 39 – 54;,
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Imidazole | C3H4N2 – PubChem

Related Products of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under ice-cooling, L-selectride (1.3 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (13 mL) solution containing (6S,8aR)-1,1-cyclopropyl-6-(3,4,5-trifluorophenyl)tetrahydropyrrolo[2,1-c][1,4]oxazine-3,4-dione (377 mg). Stirring was continued for 40 minutes at the same temperature. A 5 N sodium hydroxide solution (251 muL) was added to the reaction solution, and stirring was continued for 10 minutes at 0 C., and next hydrogen peroxide solution (245 muL, 35% solution) was added, and stirring was continued for 10 minutes at 0 C. Sodium bisulfite (260 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (13 mL) and triphenyl phosphonium bromide (439 mg) were added to the residue, and the resultant was heated under reflux for 1 hour. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (299 mg) and triethylamine (348 {L) were added, and stirring was continued for 12 hours at room temperature. Ethyl acetate and brine were added to the reaction solution, and the organic layer was partitioned. The resultant was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. The residue was crudely purified by silica gel column chromatography (carrier: Chromatrex NH, eluting solvent: hexane/ethyl acetate?ethyl acetate). A crude material (100 mg) containing the title compound was obtained. The resulting crude material (20 mg) was purified by Daicel CHIRALPAK IA (2cm¡Á25 cm: transition phase; hexane/ethanol 1/1), and the title compound (3.8 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 496 [M++H]. 1H-NMR (CDCl3) delta (ppm): 0.91-0.96 (m, 1H), 1.01-1.13 (m, 2H), 1.32-1.41 (m, 2H), 1.82-1.94 (m, 2H), 2.29 (s, 3H) 2.37-2.46 (m, 1H), 3.83 (s, 3H), 4.61 (dd, J=11.6, 4.8 Hz, 1H), 5.18 (d, J=8.8 Hz, 1H), 6.80 (s, 1H), 6.86 (dd, J=8.0, 6.0 Hz, 2H), 6.91 (dd, J=1.2, 1.2 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.26 (dd, J=8.4, 1.6 Hz, 1H), 7.36 (d, J=1.2 Hz, 1H), 7.70 (d, J=1.6 Hz, 1H).

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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

Preparation of olmesartan medoxomil Example 1 17.3 g (124.8 mmol) of K2CO3, 15 g (62.4 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (III) and 38.3 g (68.7 mmol) 4-[2-(trityltetrazol-5-yl)phenyl]-benzyl bromide (IVa) were suspended in 750 ml of acetonitrile. The suspension was then heated under reflux until the reaction was completed (7 h). 510 ml of acetonitrile were distilled off and the concentrate was cooled to 23 to 25 C. The mixture was stirred at this temperature overnight, then the suspension was cooled to 0 C and stirred at this temperature for 1 h. The crude product (Va) was filtered off and washed 2x with 20 ml of cooled acetonitrile. Wet product was suspended in 450 ml of water, stirred for 1.5 h and after that filtered off. The mass of dried product (Va) was 39.5 g (89 %). T=165-169C IR: 1666, 1525, 1291, 1446, 1177, 881, 756, 699, 640

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KRKA, tovarna zdravil, d.d., Novo mesto; EP1816131; (2007); A1;,
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Imidazole | C3H4N2 – PubChem

Application of 6160-65-2, A common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.

Step A: N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide To thiazol-2-amine (2.12 g, 21.17 mmol) in acetonitrile (30 mL) and tetrahydrofuran (5 mL) was added di(lH-imidazol-l-yl)methanethione (4.90 g, 27.5 mmol). The reaction was stirred at 60 C for 5 hours. The reaction was cooled to room temperature and the precipitate was filtered and washed with cold acetonitrile (2 x 15 mL) to afford an orange-brown powder. The product, N-(thiazol-2-yl)-lH- imidazole- l-carbothioamide (3.70 g, 17.60 mmol, 83 % yield), was taken directly to the next step without any further characterization.

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; MCDONALD, Ivar, M.; KING, Dalton; OLSON, Richard, E.; WANG, Nenghui; IWUAGWU, Christiana, I.; ZUSI, Christopher, F.; MACOR, John, E.; WO2011/53292; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem