Month: November 2020

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. 139481-72-4, name is Trityl candesartan belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 139481-72-4

Potassium carbonate (60 gm), 1-chloroethylcyclohexyl carbonate (60 gm) and potassium iodide (20 gm) were added to the solution of 2-Ethoxy-1-[[2′-(N- triphenylmethyltetrazole-5-yl)biphenyl)-4-yl]methyl]benzimidazole-7-carboxylic acid (100 gm) in dimethylformamide (500 ml) at room temperature. Raised the temperature to 750C, stirred for 2 hours, cooled to room temperature and 5% sodium chloride solution (2000 ml) was added. Maintained for 15 minutes, ethyl acetate (400 ml) was added, stirred and separated the layers. Aqueous layer was extracted with ethyl acetate (400 ml), organic layer was taken, washed with 10% sodium chloride solution (400 ml), concentrated, and co-distilled with ethyl acetate (100 ml). Mixture of ethyl acetate (500 ml) and n-hexane (500 ml) were added to the residual mass, stirred for 6 hours at room temperature, cooled to 50C, stirred for 1 hour, filtered, then washed with mixture of ethyl acetate (50 ml) and n-hexane (200 ml) and dried for 6 hours to obtain 1-(Cyclohexyloxy carbonyloxy)ethyl-2-ethoxy-1-[[2′-(1H-tetrazole-5-yl)biphenyl-4-yl]methyl] benzimidazole-7-carboxylate (110 gm, HPLC Purity: 99%).

The synthetic route of 139481-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HETERO RESEARCH FOUNDATION; WO2009/157001; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, Adding some certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4.

33.1 1-(4-nitrophenyl)-1H-imidazole: 9 g (64.5 mmoles) of potassium carbonate and 5 g (3.75 ml; 35.2 mmol) of 1-fluoro-4-nitrobenzene are added to a solution of 2 g of imidazole (29.4 mmol) in 14 ml of DMF. The reaction mixture is agitated for 1.5 hours at 110 C. Ethyl acetate (50 ml) is added to the medium which is washed 3 times with 50 ml of water. The organic phases are dried over magnesium sulphate and concentrated under vacuum. 4.4 g of product are thus obtained (yield=80%) in the form of a clear oil and used without further purification in the following stages. NMR 1H (CDCl3, 100 MHz, delta): 6.92 (t, 1H, Arom. H imidazole), 7.16 (s, 1H, Arom. H imidazole), 7.24-7.32-8.18-8.27 (4s, 4H, Arom. H), 7.59 (s, 1H, Arom. H imidazole).

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 288-32-4.

Reference:
Patent; Chabrier de Lassauniere, Pierre Etienne; Auvin, Serge; Bigg, Dennis; Auguet, Michel; Harnett, Jeremiah; US2003/78420; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-54-5, A common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, molecular formula is C8H7ClN2O, 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 33 2-Chloro-5-methoxy-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole 2-Chloro-5-methoxy-1H-benzimidazole (0.661 g, 3.6 mmol) was coupled to 1,2,3-tri-O-acetyl-5deoxy-D-ribofuranose according to General Procedure II. The crude product was purified by flash chromatography (9:1 methylene chloride/ether) to yield the title compound (0.900 g, 65%) as a ~1:1 mix of regioisomers (1H NMR); MS (AP): m/z 405 (M+Na); 1H NMR (DMSO-d6) delta: 7.65-7.54 (two d, 1H), 7.21 (s, 1H), 6.97 (m, 1H), 6.18-6.11 (two d, 1H), 5.70-5.59 (m, 1H), 5.21 (q, 1H), 4.27 (m, 1H), 3.83 (two s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 1.51 (t, 3H).

The synthetic route of 15965-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Glaxo Wellcome Inc.; US6413938; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below.

To a suspension of 10 (4.94 g, 51.4 mmol) in dry THF (30 mL) was added NaH (2.48 g, assey 60%, 61.9mmol, 1.2 eq) at -78 C under argon atmosphere, and stirred for 10 min at rt. The reaction mixture was cooledto -78 C and added MeI (3.9 ml, 62.6 mmol, 1.2 eq) dropwise at -78 C. The mixture was gradually warmed to rt and stirred for 18 h. The mixture was quenched with MeOH, then concentrated in vacuo. The residue was dissolved with CH2Cl2 and the solution was filtered through a pad of Celite to afford the crude product, which was purified by silica gel chromatography (20:1 CHCl3 / MeOH) to afford 15 (5.58 g, 99%) as a yellow oil. 1H NMR (500 MHz, CDCl3) delta 3.79 (s, 3H), 7.53 (s, 1H), 7.60 (s, 1H), 9.88 (s, 1H)

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; Yamashita, Megumi; Shimizu, Keita; Koizumi, Yasuaki; Wakimoto, Toshiyuki; Hamashima, Yoshitaka; Asakawa, Tomohiro; Inai, Makoto; Kan, Toshiyuki; Synlett; vol. 27; 19; (2016); p. 2734 – 2736;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Adding some certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1.

Diethyl azodicarboxylate (174 mg, 1 mmol) was added to a solution of 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (288 mg, 0.5 mmol), triphenylphosphine (262 mg, 1 mmol) and 2-(imidazol-1-yl)ethanol (62 mg, 0.55 mmol), (J. Med. Chem. 1993, 25, 4052-4060), in methylene chloride (5 ml) and the mixture stirred for 1 hour at ambient temperature. Acetic acid (30 mg, 0.5 mmol) was added and the volatiles were removed by evaporation. The residue was triturated with ether, the solid collected by filtration and dried under vacuum to give 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (186 mg, 55%). MS – ESI: 668 [MH]+

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 1615-14-1.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

e) {(S)-3-[4-(5-Amino-6-methoxy-pyridin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-pyrrolidin-1-yl}-(1-methyl-1H-imidazol-4-yl)-methanone A solution of 1-methyl-1H-imidazole-4-carboxylic acid (CAS registry 41716-18-1) (36.0 mg, 0.26 mmol) and Et3N (0.11 ml, 0.78 mmol) in DMF (1 ml) was treated with HBTU (CAS registry 94790-37) (107 mg, 0.28 mmol). After stirring at rt for 20 min, the reaction mixture was cooled down to 5¡ã C. and a solution of 2-methoxy-5-[6-((S)-pyrrolidin-3-yloxy)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-pyridin-3-ylamine (88 mg, 0.26 mmol) in DMF (3 ml) was added. The reaction mixture was stirred at rt for 1 h, concentrated and the residue was taken up in DCM (10 ml), washed with a sat. aq. NaHCO3 soln. (5 ml), the organic layer was separated by elution through a separating phase cartridge and concentrated. The residue was purified by flash chromatography on silica gel (heptane/EtOAc 100:0 to 0:100), the combined fractions were concentrated, dissolved in tBuOH/H2O and lyophilized to afford the title compound as a colourless solid (21 mg, 37percent yield). UPLC RtM2=0.85 min; ESIMS: 451 [(M+H)+]. 1H NMR (400 MHz, CD3OD): delta 7.64 (s, 1H), 7.62 (s, 1H), 7.65 m, 1H), 6.93 (m, 1H), 6.70 (m, 1H), 6.20-6.34 (m, 1H), 6.15 (m, 1H), 4.81 (m, 1H), 4.19-4.31 (m, 2H), 3.90-4.05 (m, 4H), 3.55-3.83 (m, 8H), 2.04-2.28 (m, 2H).

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, 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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below.

General procedure: The corresponding imidazole (2 mmol) and 2-bromoethanol or 3-bromo-1-propanol or 4-bromo-1-butanol (2.4 mmol) dissolved in acetone (20 ml). Then K2CO3(6 mmol) and KI (2 mmol) were added. The reaction mixture was stirred at 60oCfor 12h. Filtered, the filtrate was concentrated under reduced pressure and dried under vacuum. The1H-NMR and13C-NMR were consistent with the literature.

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:
Article; Hu, Yanping; Li, Na; Zhang, Jiayao; Wang, Ying; Chen, Li; Sun, Jianbo; Bioorganic and Medicinal Chemistry Letters; vol. 29; 9; (2019); p. 1138 – 1142;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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 144689-93-0.

20L reactor was added 300.0g (1.25mol) imidazole mono-, 1043.6g (1.87mol) BBTT, 44.8g (1.87mol) of lithium hydroxide and 7kg acetonitrile. The reaction system was increased to 70-75 5h, TLC or HPLC in control, raw reaction was complete. After cooling to 30-45 system To the system was added in portions 280.6g (5.0mol) of potassium hydroxide and 700g of water to form a solution. Plus complete, insulation reaction 4-5h, TLC or HPLC in control, raw reaction was complete. After 300g of water added to the system dropwise acetic acid adjusted to pH 5.5 to 6.5. After stirring for 1h incubation continued cooling to room temperature, filtered, the filter cake washed with a small amount of acetone to obtain 777.4g of intermediate 5 run. HPLC: 95.9%,Yield: 90.4%.

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Bang Pharmaceutical Co., Ltd.; Zhao, Guangrong; Huan, Shuang; Zhao, Huayang; Liu, Liping; Chen, Guoping; Tang, Jingyu; (19 pag.)CN105481842; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 15788-16-6, name is 1H-Benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O2, 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. 15788-16-6.

Preparation 26 Methyl 5-benzimidazolecarboxylate A mixture of 10 g of 5-benzimidazolecarboxylic acid, 150 ml of methanol and 100 ml of a 4N solution of hydrogen chloride in 1,4-dioxane was agitated ultrasonically for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, after which 300 ml of methanol and 3.5 g of lithium borohydride were added to the residue and the mixture was stirred for 1 hour. The solvent was then removed by evaporation under reduced pressure and the residue was mixed with an aqueous solution of sodium chloride, after which it was extracted with ethyl acetate. The solvent was removed by distillation under reduced pressure, to give 5.44 g of the title compound, melting at 136-138 C.

The synthetic route of 1H-Benzo[d]imidazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5886014; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, 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 934-22-5 as follows.

Example 133; N-1H-Benzimidazol-5-yl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 2,2,2-Trichloroethyl 1H-benzimidazol-5-ylcarbamate; To a solution of 1H-benzimidazol-5-amine (1.00 g, 7.51 mmol) and pyridine (0.73 ml, 9.01 mmol) in tetrahydrofuran (25 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.25 ml, 9.01 mmol), and the mixture was stirred at room temperature for 1.5 hour . Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 1.49 g (64.4%) of the desired product as a solid was separated by filtration. 1H-NMR (CDCl3) delta; 5.22 (2H, s), 7.27 – 7.29 (1H, m), 7.90 – 8.01 (2H, m), 8.06 (1H, br s), 8.56 (1H, s), 10.16 (1H, br s).

According to the analysis of related databases, 6-Aminobenzimidazole, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem