Author: Jessica.F

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 150058-27-8 as follows. Safety of Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

The 45g2-ethoxy -1H-benzimidazole-7-carboxylic acid and 500 ml by adding dichloromethane for added to a reaction flask, stirring cooling to 20 °C the following, to-drop 50.7g triethylamine, the drop finishes, drop by adding 54.0g to toluene sulfonyl chloride and 100 ml dichloromethane mixed solution, drop Bi Yu 10-20 °C stirring reaction 3h, for 10-20 °C adding 39.7g4-hydroxymethyl-5-methyl -1,3-dioxol-2-one, the temperature rising to adding 30-40 °C stirring reaction, with used in HPLC. After the reaction is complete, cooling to 15-25°C, by adding 400 ml purified water stirring, layered, with 30g drying by anhydrous sodium sulfate. Decompression jeung dry dichloromethane, by adding 300 ml methyl tert-butyl ether refined, cooling to 0-5 °C stirring crystallization 3h, filtering, with 20 ml cool to 0-5 °C methyl tert-butyl ether washing, for 40-50 °C reduced-pressure drying to the job (5-methyl-2-oxo -1,3-dioxol-4-yl) methyl 2-ethoxy -1H-benzo[d] imidazol-7-carboxylic acid ester 63.6 g. The yield of 91.6percent, purity 98.1percent

According to the analysis of related databases, 150058-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Long days Chongqing Pharmaceutical Co., Ltd; Meng, Wenxue; Long, Daobing; Chen, Shunxiang; (14 pag.)CN105622595; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1243204-92-3, A common heterocyclic compound, 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, molecular formula is C12H11N3O, 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.

b) Preparation of intermediate 2 and 2a. A stirred sol. of intermediate 1 (1.40 g, 6.57 mmol) in anhydrous EtOH (1.4 ml) and Et2O (28 ml) was cooled at 0 0C. HCl gas was bubbled through the contents for 20 min, then the ensuing r.m. left to stir overnight at r.t. The precipitated product was collected by filtration and dried to give the HCl salt of the desired product as an off-white solid. Yield: 1.72 g of intermediate 2 (78.9%). Intermediate 2 was used as such in the next reaction step, or was converted into the free base by dissolving it in water, basifying the solution via addition of Na2Ctheta3, and extraction of the resulting suspension with DCM. The organic layer was dried (MgSO4), filtered and cone, in vacuo to yield intermediate 2a (quantitative yield).

The synthetic route of 1243204-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10597-52-1, A common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, 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.

4-Nitro-1-(3-nitrophenyl)benzimidazole was prepared analogueously to 3 g from 4-nitrobenzimidazole and 1-fluoro-3-nitrobenzene. Mp 260-262 C. 1-(3-Aminophenyl)-4-nitrobenzimidazole was prepared from 4-nitro-1-(3-nitrophenyl)benzimidazole as described in Example 3a. Mp 159-161 C.

The synthetic route of 10597-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NeuroSearch A/S; Meiji Seika Kaisha, Ltd.; US5554630; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-13-3, These common heterocyclic compound, 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic 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.

Example 17; N- 3 -(2, 5 ‘-Bipyrimidin-4-ylamino”)-4-methylphenyll -3 -(4-methy 1- 1 iZ-imidazol- 1 -vD-5- (trifluoromethyDbenzamide; A solution of 3 -(4-methy 1- 1 H-imidazol- 1 -y l)-5 -(trifluoromethyl)benzoic acid (Method27; 100 mg5 0.36 mmol), N3-255’-bipyrimidin-4-yl-4-methylbenzene-l53-diamine (Method 20; 97 mg5 0.36 mmol) and DIEA (0.25 ml, 1.08 mmol) in DMF (5 ml) was treated with HATU (205 mg, 0.40 mmol). The reaction mixture was stirred for 15 h at 25 C. The reaction was quenched with 10% NaOH and extracted with EtOAc. The organics were dried with NaCl(sat) and then Na2SO4(S) and removed under reduced pressure. The residue was purified by reverse phase semi-preparative chromatography to give the title compound. NMR (300 MHz): 10.75 (s, IH)5 9.75 (s, IH), 9.45 (s, 2H)5 9.41 (s, IH), 9.21 (s, IH)5 8.66 (s, IH), 8.33 – 8.45 (m, 3H), 8.17 – 8.22 (m, 2H), 7.52 (d, IH), 7.27 (d, IH)5 6.73 (d, IH)5 2.31 (s, 3H)5 2.19 (s, 3H); m/z 531.

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid is playing an increasingly important role. we look forward to future research findings about 641571-13-3.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/79791; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, 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 17228-38-5, name: N-Methyl-1H-benzo[d]imidazol-2-amine

(5R,8aS)-3-Chloro-1 -(1 -methanesulfonyl-1 -methyl-ethyl)-5-methyl-5,6,8a,9- tetrahydro-8H-7,1 0-dioxa-2,4,4b-triaza-phenanthrene (1 .85 g), benzimidazole2-yl-methylamine (719 mg), tris(dibenzylideneacetone)dipalladium(0) (895 mg; 0.2 eq.) and dicyclohexyl-(2?,4?,6?-triisopropyl-biphenyl-2-yl)-phosphane (932 mg) were dissolved in dioxane (10 ml), lithium tert-butoxide (1,0 M solution in tetrahydrofuran) (6.8 ml, 1.4 eq) was added and the mixture was stirred for 1 h at 80 00. The reaction mixture was purified by chromatography(dichloromethane I methanol) to afford {1 -[(5R,8aS)-1 -(1 -Methanesulfonyl-1 -methyl-ethyl )-5-methyl -5,6 ,8a ,9-tetrahyd ro-8 H-7, 1 0-d ioxa-2 ,4 ,4b-triaza-phenanthren-3-yl]-1 H-benzimidazol-2-yl}-methyl-amine as a yellow solid (1 .18g); LCMS (method E): 0.50 mm (purity 98%); [MH+] 473.3 mlz; 1H NMR (500MHz, DMSO-d6) 6 8.19 (q, J = 4.8 Hz, 1 H), 8.00 (d, J = 7.6 Hz, 1 H), 7.28 -7.21 (m, 1 H), 7.07 (td, J = 7.6, 1 .2 Hz, 1 H), 6.97 (td, J = 7.7, 1 .3 Hz, 1 H), 4.63 (qd, J = 6.8, 2.9 Hz, 1 H), 4.43 (dd, J = 11 .0, 3.4 Hz, 1 H), 4.04 – 3.94 (m, 2H),3.88 (d, J= 11.6 Hz, 1H), 3.83 (dd, J= 11.1,9.2Hz, 1H), 3.70 (dd, J 11.6,3.2 Hz, 1 H), 3.22 -3.15 (m, 1 H), 3.05-3.01 (m, 6H), 1.84 (5, 3H), 1.81(s, 3H), 1 .35 (d, J = 6.8 Hz, 3H)and (1 H-Benzimidazol-2-yl)-[(5R,8aS)-1 -(1 -methanesulfonyl-1 -methyl-ethyl)-5- methyl-5,6,8a,9-tetrahydro-8H-7, 1 0-dioxa-2,4,4b-triaza-phenanthren-3-yl]-methyl-amine as a beige solid (722 mg); LCMS (method E): 0.53 mm (purity94%);[MH+]473.3m/z; 1H NMR (400 MHz, DMSO-d6)o 12.40(s, 1H),7.45-7.38 (m, 1 H), 7.34 – 7.27 (m, 1 H), 7.11 – 7.00 (m, 2H), 4.67 (qd, J = 6.5, 2.7Hz, 1 H), 4.38 (dd, J = 11 .0, 3.5 Hz, 1 H), 3.99 – 3.89 (m, 2H), 3.82 (d, J = 11.5Hz, 1 H), 3.76 (dd, J = 11 .0, 8.8 Hz, 1 H), 3.72 (s, 3H), 3.65 (dd, J = 11.7, 3.3 Hz, 1H), 3.15 (t, J= 11.8 Hz, 1H), 3.04 (s, 3H), 1.83 (s, 3H), 1.81 (s, 3H), 1.29(d, J = 6.8 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Methyl-1H-benzo[d]imidazol-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; BURGDORF, Lars; DORSCH, Dieter; TSAKLAKIDIS, Christos; (189 pag.)WO2017/202748; (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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H3BrN2

Intermediate E-0 (13.6 g) was dissolved in 80 mL of NMP and compound 275-4 (6.5 g) and Na2C03 (4.6 g) were added. The solution was stirred at 90 C for 6 h, then NMP was removed under reduced pressure. The residue was dissolved in EtOAc, washed with water and purified by silica gel flash chromatography (PE: EA= 2: 1) to give compound 275-5 as a yellow oil.

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; ELAN PHARMACEUTICALS, INC.; NEITZ, R., Jeffrey; TROUNG, Anh, P.; GALEMMO, Robert, A.; YE, Xiaocong, Michael; SEALY, Jennifer; ADLER, Marc; BOWERS, Simeon; BEROZA, Paul; ANDERSON, John, P.; AUBELE, Danielle, L.; ARTIS, Dean, Richard; HOM, Roy, K.; ZHU, Yong-liang; WO2012/48129; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-methyl-2-n-propyl-1H-benzimidazole-6-carboxylic (1, 2.18g, 10mmol) and thionyl chloride (20mL, 280mmol) was refluxed for 3h, then the excess thionyl chloride was removed under reduced pressure to obtain the crude acyl chloride (2) as an off-white solid. It was used for the next step directly.

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jun; Wang, Jin-Liang; Yu, Wei-Fa; Zhou, Zhi-Ming; Tao, Wen-Chang; Wang, Yi-Cheng; Xue, Wei-Zhe; Xu, Di; Hao, Li-Ping; Han, Xiao-Feng; Fei, Fan; Liu, Ting; Liang, Ai-Hua; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 44 – 54;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 137049-00-4, 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. 137049-00-4 name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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 methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate (Step 6, Example 1) (1.0 equiv) and Et3N (3.0 equiv) or pyridine (3.0 equiv) in CH2Cl2 (0.05 M) was added 1-methylimidazole-4-sulfonyl chloride (1.2 equiv). The reaction was monitored by TLC (10% MeOH-CH2Cl2) and was heated if necessary. After 30 min the mixture was poured into saturated sodium bicarbonate and extracted with CH2Cl2. The combined organic phase was washed with brine, dried over sodium sulfate and purified by column chromatography to afford 92% of the desired product.

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

Reference:
Patent; Wyeth; US2008/9485; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 2034-22-2 as follows. Safety of 2,4,5-Tribromoimidazole

Step 1: N-(2.4.5-tribromo-l-(r2-(trimethylsilv?ethoxy1methyl|-lH-imidazole (A1); To a solution of 2,4,5-tribromo-imidazole in THF was added portionwise sodium hydride (1 eq.). The mixture was stirred for 20 min at RT and SEM-Cl (1 eq.) was added. The mixture was left stirring for 16 h at RT. After dilution with Et2O the suspension was filtered and the clear solution was concentrated to dryness under reduced pressure. The oily residue was dissolved in PE/ 5% EtOAc and applied on a silicagel column. After washing with PE/ 5% EtOAc the product was eluted with PE/ 10% EtOAc. The solvents were removed under vacuum to afford the title compound as a white solid. 1U NMR (400 MHz, CDCl3) delta: 5.31 (s, 2H), 3.59 (t, J=7.8 Hz, 2H), 0.92 (t, J=7.8 Hz, 2H), 0.01 (s, 9H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2008/56187; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem