Month: March 2021

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. 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H9BrN2

General procedure: 2-(2-Bromophenyl)benzimidazole (1 mmol), substituted aldehyde (1.2 mmol), NaN3 (1.8 mmol), Cu (10mol%), L-proline (20 mol%), and Cs2CO3 (1 mmol) were added to DMF in a 50 mL round bottom flask, and then the mixture was refluxed at 80 C for 16 h under nitrogen atmosphere. TLC was monitored the reaction till completed, and then the reaction mixture was cooled to room temperature. The mixture was poured into the dichloromethane, washed with brine and water. The organic layer was concentrated with evaporator, and the residue was purified by column chromatography on silica gel to give the target compound (A-4 to A-37).

According to the analysis of related databases, 13275-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jun-cai; Wang, Ren-xuan; Sun, Yu; Zhu, Jia-kai; Hu, Guan-fang; Wang, Yu-ling; Zhou, Rui; Zhao, Zhong-min; Liu, Ying-qian; Peng, Jing-wen; Yan, Yin-fang; Shang, Xiao-fei; Bioorganic Chemistry; vol. 92; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H11N3

General procedure: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8).

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 2963-77-1.

Reference:
Article; L’abbate, Fabrizio P.; Mueller, Ronel; Openshaw, Roxanne; Combrinck, Jill M.; de Villiers, Katherine A.; Hunter, Roger; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 243 – 254;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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, Quality Control of Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

Example 1 :Preparation of trityl olmesartan medoxomilEthyl-4-( 1 -hydroxy- 1 -methylethyl)-2-propyl-imidazole-5-carboxylate ( 100 gm) was dissolved in acetone (2500 ml) and then added potassium carbonate (100 gm), 5-[4′- (bromomethyl)[ 1,1 ‘-biphenyl] -2-yl]-2-(triphenylmethyl)-lH-tetrazole (250 gm) and tert- butyl ammonium bromide (15 gm) under stirring at room temperature. The temperature of the reaction mass was raised to 50 to 55C and maintained for 15 hours at 50 to 55C. The reaction mass was cooled to 45C and passed over celite bed. The collected filtrate was cooled to 0 to 5C and then added a solution of potassium carbonate (36 gm) in water (36 ml) for 1 hour. The temperature of the reaction mass was raised to room temperature and maintained for 16 hours at room temperature. The acetone was distilled off completely under vacuum at below 40C to obtain residue. To the residue was added sodium chloride solution (10%, 900 ml) and then added ethyl acetate (1500 ml). The layers were separated and the aqueous layer was extracted. Combined the both organic layers and dried over sodium sulfate. The solvent was distilled off completely to obtain a residual mass. A mixture of acetone (1200 ml), potassium carbonate (100 gm), (4- bromoethyl)-5-methyl-oxo-l,3-dioxane (105 gm) and potassium iodide (17 gm) were added under stirring at room temperature and then the contents were heated to 50 to 55C. The solution was added to the above residual mass for 1 hour 30 minutes and maintained for 1 hour 30 minutes at 50 to 55C. The reaction mass was cooled to 45C and filtered. The solvent was distilled off completely to obtain residue. Toluene (1500 ml) was added to the residue and the layers were separated. The toluene layer was dried over sodium sulfate and distilled off the layer under vacuum up to obtain clear residual mass. To the residual mass was added methanol (1500 ml) and stirred for 30 minutes at room temperature. The reaction mass was cooled to 10 to 15C and maintained for 1 hour 30 minutes. The separated solid was filtered and dried at 40 to 45C for 7 hours to obtain 270 gm of trityl olmesartan medoxomil.Trityl olmesartan medoxomil: 98.5%;Trityl olmesartan ethyl ester impurity: 0.35%;Bromo trityl olmesartan medoxomil impurity: 0.35%;Methyl trityl olmesartan medoxomil impurity: 0.34%.

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; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; MURALIDHARA REDDY, Dasari; RAJI REDDY, Rapolu; RAMAKRISHNA REDDY, Matta; VAMSI KRISHNA, Bandi; WO2012/1694; (2012); 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. 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

Ethyl 2-BENZIMIDAZOL-2-YLACETATE (1.1 equivalents) and 2-amino- 5-(4-METHYLPIPERAZINYL) BENZENECARBONITRILE (1.0 equivalent) were dissolved in 1, 2-dichloroethane, and then SNCL4 (11 equivalents) was added. The mixture was heated at reflux overnight. Upon cooling, the mixture was concentrated in vacuo. NAOH (3 M) was added to the solid, and the mixture heated at 80 C for 0.5 hours. The solid was filtered and washed sequentially with H2O, CH2CI2, and acetone. LC/MS indicated that the product was present in the acetone layer and the solid. These fractions were combined and purified by silica gel chromatography (5-10% MeOH in CH2CI2 with 1 % ET) to give the desired product. LC/MS M/Z 375.4 (MH+), Rt 1.65 minutes.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; WO2004/18419; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, These common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 solutionof amine 3-(4-methyl-1H-imidazol-1-yl)-5-(triuoromethyl)aniline (a) (one equivalent) and Et3N(1.5 equivalents) in dry CHCl3 cooled to 0 C was added dropwise to a solution of4-(chloromethyl)benzoyl chloride (4) (one equivalent) in dry CHCl3. The reaction mixture wasstirred at room temperature. The progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated, and the water layer was extracted by CHCl3 threetimes. The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum.The product was purified by column chromatography on silica gel. The white solid 5 was given with 60% yield; m.p. 80-82 C; 1H-NMR (DMSO-d6, 500 MHz) : 10.74 (s, 1H), 8.32 (s, 1H), 8.26 (d,J = 1.0 Hz, 1H), 8.17 (s, 1H), 8.03 (d, J = 8.3 Hz, 2H), 7.77 (s, 1H), 7.66 (d, J = 8.0 Hz, 2H), 7.52 (s, 1H),4.89 (s, 2H), 2.21 (s, 3H); 13C-NMR (DMSO-d6, 125 MHz) : 166.1, 142.2, 141.7, 139.4, 138.4, 135.5, 134.4,129.4, 128.6, 115.4, 114.7, 112.2, 45.8, 14.0; HRMS (ESI+) m/z calculated for C19H16ClF3N3O [M + H]+394.0929, found 394.0927; purity: 97.93% (by HPLC).

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 641571-11-1.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

18672-03-2, name is 5,6-Dichloro-1H-benzo[d]imidazol-2-amine, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 5,6-Dichloro-1H-benzo[d]imidazol-2-amine

EXAMPLE 25 7,8-Dichloro-1,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4(3H)-one Reaction of 2-amino-5,6-dichlorobenzimidazole with acetone and methyl isocyanate according to the procedure of Example 1, first paragraph, provided the title compound. In this case, a 10-N-methylcarbamoyl derivative was not isolated from the reaction mixture. The product was recrystallized from acetone to give a solid, mp 220 C. (dec.). The confirmatory elemental analysis is shown in Table III.

The synthetic route of 18672-03-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Union Carbide Corporation; US4497650; (1985); A;; ; Patent; Union Carbide Corporation; US4498920; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic acid, 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 16042-25-4, Quality Control of 2-Imidazolecarboxylic acid

N-((3R,11R,E)-5,12-dioxo-3-phenyl-1-oxa-4-azacyclododec-8-en-11-yl)-1H-imidazole-2-carboxamide Under nitrogen, 1H-imidazole-2-carboxylic acid (8.40 mg, 0.075 mmol) was dissolved in anhydrous DMF (1.2 ml) with (iPr)2EtN (48.0 mul, 0.277 mmol). Next, the TFA salt form of (3R,11R,E)-11-amino-3-phenyl-1-oxa-4-azacyclododec-8 ene-5,12-dione (30.0 mg, 0.075 mmol), 1-hydroxybenzotriazole (15.93 mg, 0.104 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (19.95 mg, 0.104 mmol) were added. The reaction mixture was stirred overnight (15 hours). Upon completion of the reaction, the reaction was diluted with EtOAc. The crude mixture was washed twice with saturated NH4Cl (*2), the half-saturated NaHCO3, and brine. The crude mixture was dried over Na2SO4 and concentrated under vacuum to yield a white wax. The product (23.8 mg) was isolated via silica chromatography using an ISCO automated system (MeOH/DCM gradient) in 90% yield in the form of a white solid. LRMS (ESI+) (M+H): 383.17

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Imidazolecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Buhrlage, Sara; Dockendorff, Chris; Foley, Mike; Kim, Han-Je; Germain, Andrew; MacPherson, Lawrence; Nag, Partha; Schreiber, Stuart; Ting, Amal; Weiwer, Michel; Youngsaye, Willmen; US2014/94462; (2014); 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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 96797-15-8

4-Iodo-1-trityl-1H-imidazole (5, 2 g, 4.58 mmol), (5-chloro-2-methoxyphenyl)boronic acid(0.852 g, 4.58 mmol), K3PO4 (2.9 g, 13.7 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol) were added todry dimethylformamide (30 mL). The reaction mixture was stirred at 100 C under inert atmosphere,until the starting material disappeared in TLC. The reaction mixture was distilled in vacuo, and ethylacetate (100 mL) was added to the mixture. The organic extract was washed twice with saturatedaqueous NaCl (20 mL), and the organic extract was dried over Na2SO4. After solvent was removedunder vacuum, the product was purified as a white solid by silica gel column chromatography, 1.2 g,yield 63%. 1H-NMR (400 MHz, CDCl3): = 7.51-7.32 (m, 12H, H-phenyl, H-imidazolyl), 7.15-7.04 (m,8H, H-phenyl, H-imidazolyl), 6.94 (d, J = 8.1 Hz, 1H, H-phenyl), 3.99 (s, 3H, CH3). HRMS (ESI): m/z[M + H]+ calculated for C29H25N2O: 417.19614; found: 417.19647.

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; Wen, Hui; Liu, Yuke; Wang, Shufang; Wang, Ting; Zhang, Gang; Chen, Xiaoguang; Li, Yan; Cui, Huaqing; Lai, Fangfang; Sheng, Li; Molecules; vol. 24; 11; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

-78 in N2under a 100 mL 3-neck round bottom flask in then-BuLi(hexane of 2.5 M, 0.52 mL, 1.3 mmol) to dry THF (10 mL) of 6-bromo-2,4-dichloro- 3- (2-chlorophenyl) quinolone (387.5 mg, 1 mmol, intermediate 2: step c) was added dropwise to a solution of.30 bungan continuous stirring, and then the, -78 in dry THF (10 mL) of 1-methyl -1H-imidazole-5-carbaldehyde(110 mg, 1 mmol) was added to the solution.The cooling bath was removed and was gradually The mixture was warmed to RT, stirred for 2 hours.The mixture H2next quenched by the addition of O (10 mL), CH2Cl2and extracted with (2 ¡Á 50 mL).The combined organic phases Na2SO4dried and concentrated dry, prep-TLC (CH3OH / CH2Cl2to give evolves to 1:40) to give the title compound as a white solid.

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-1H-imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 930-62-1, 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. 930-62-1 name is 2,4-Dimethylimidazole, 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.

Synthesis of 2-imidazol-1 -yl-ethylamine derivatives by lambda/-alkylation of disubstituted imidazoles [general procedure (GP9)]Sodium hydroxide (180 mmol; powder) and tetrabutylammonium hydrogensulfate (1.80 mmol) were successively added to a solution of the respective imidazole derivative (45.00 mmol) in MeCN (100 ml). After 30 min., 2-chloroethylamine hydrochloride (54.00 mmol) was added and the reaction mixture was stirred for 24h at reflux. The obtained suspension was filtered and the filtrate was concentrated in vacuo to give a crude oil which was used without further purification.2-(2,4-dimethyl-imidazol-1-yl)-ethylamine Prepared by lambda/-alkylation of 2, 4-dimethyl-1 /-/-imidazole according to the previously described general procedure (GP9).1H-NMR (CDCI3; 300 MHz): delta = 6.50 (s; 1 H), 3.76 (t, J = 6.2 Hz, 2H), 2.91 (t, J = 6.2 Hz, 2H), 2.28 (s, 3H), 2.09 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dimethylimidazole, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/78291; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem