Month: November 2020

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., 3034-50-2

Dry triethylamine (12.6 mL, 90.0 mmol) was added drop wise over two hours to a slurry of (l,3)-H-imidazole-4-carbaldehyde (5.0 g, 52 mmol) and trityl chloride (16.0 g, 57.0 mmol) in acetonitrile (170 mL). After complete addition of the triethylamine, the resulting solution was stirred overnight and then hexane (16.6 mL) and water (170 mL) were added. After stirring for an additional 30 minutes, the resulting solid was collected and dried overnight under vacuum to provide the title compound as a white solid (16.8 g, 96%). 1H NMR (400 MHz, CDCl3): delta 9.81 (s, IH), EPO 7.54 (s, IH), 7.46 (s, IH), 7.29 (m, 10H), 7.04 (m, 5H). 13C NMR (100 MHz, CDCl3): delta 186.9, 141.9, 141.2, 141.0, 130.0, 129.0, 128.9, 127.2, 76.7.

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; YALE UNIVERSITY; UNIVERSITY OF SOUTH FLORIDA; UNIVERSITY OF WASHINGTON; SEBTI, Said; WO2006/102159; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

7098-07-9, 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. 7098-07-9, name is 1-Ethyl-1H-imidazole, A new synthetic method of this compound is introduced below.

Dichloromethane (1.699 g, 20 mmol)And 1-ethylimidazole (5.768 g, 60 mmol) was added to the reaction flask.Then, after reacting in a closed vessel at 75 C for 24 h, after the reaction is completed, it is cooled to room temperature, and the solvent is evaporated to dryness.Dissolved in a small amount of methanol, added to a large amount of tetrahydrofuran and stirred at room temperature for 2 h.There are a lot of white solids generated,Filtered, washed with tetrahydrofuran, dried in vacuo,A white solid was obtained to give the title compound 2.48 g, yield 44.8%.

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; Sun Yat-sen University; Mao Zongwan; Li Yi; Tan Caiping; Huang Huazhen; Ji Liangnian; (12 pag.)CN104230998; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 144689-93-0.

Example 2; Preparation of olmesartan medoxomilTo dimethyl acetamide (600 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (100 gms) and powdered potassium hydroxide (50 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (270 gms) at 45-50C. The contents were stirred for 5 hours at 45-50C. Diisopropylethyl amine (200 ml) was charged to the reaction mass at 40-450C. To this was slowly added a solution of 5-methyl-2-oxo- 1 ,3-dioxane-4-yl)methyl chloride (160 gms) diluted with dimethyl acetamide (320 ml) at 40- 45C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C and was neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganic impurities. The reaction mass was charcoalized using charcoal (20 gms) and was stirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was acidified with hydrochloric acid (200 ml) slowly at 25-300C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-50C and was filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (1000 ml), neutralized with base and extracted in dichloromethane (1000 ml). The clear dichloromethane extract was then concentrated under reduced pressure, stripped off with acetone. The residue thus obtained was isolated from the acetone (500 ml) to give 110 gms of the title compound. Chromatogrphic purity- > 99%; Example 4Preparation of trityl olmesartan medoxomilTo dimethyl acetamide (300 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (50 gms) and powdered potassium hydroxide (25 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (135 gms) at 45-500C. The contents were stirred for 5 hours at 45-500C. Diisopropylethyl amine (100 ml) was charged to the reaction mass at 40-45C. To this was slowly added a solution of 5-methyl-2-oxo- 1 ,3-dioxane-4-yl) methyl chloride (80 gms) diluted with dimethyl acetamide (160 ml) at 40- 45C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C. and was neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganics. The reaction mass was charcoalized using charcoal (10 gms) and was stirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was quenched with purified water(200 ml)at 25-30C over a period of 3-4 hours. The contents were stirred at 25-300C for 30 minutes. Crude trityl olmesartan medoxomil was isolated by filtration, slurried in water (500 ml), centrifuged and dried under reduced pressure at 45-50C.

The synthetic route of Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIPLA LIMITED; CURTIS, Philip, Anthony; WO2008/43996; (2008); A2;,
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 3314-30-5 as follows. 3314-30-5

To a mixture of X4-011-1 (2 g, 12.4 mmol) and 1H-benzo[d]imidazole-2- carbaldehyde (2.72 g, 18.6 mmol) in MeOH (60 ml) was added a solution of NaOH (992 mg, 24.8 mmol) in H20 (4 ml) at 0 ¡ãC and the mixture was stirred at room temperature for 3 h. The solution was adjusted pH to 8 with 35percent HC1 aq., dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography to give X4-011-2 (2.7 g, 75.2 percent yield) as a yellow solid. LCMS (Agilent LCMS 1200-6110, Column: Waters XBridge C18 (50 mm*4.6 mm*3.5 jim); Column Temperature: 40 ¡ãC; Flow Rate: 2.0 mL/min; Mobile Phase: from 95percent [0.05percent aq. TFA] and 5percent [CH3CN + 0.05percent TFA] to 0percent [0.05percent aq. TFA] and 100percent [CH3CN + 0.05 percent TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95percent [0.05percent aq. TFA] and 5percent [CH3CN + 0.05percent TFA] in 0.05 mm and under this condition for 0.7 mi. Purity: 99percent; Rt = 1.32 mm; MS Calcd.: 289.1; MS Found: 290.1 [M+H].

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (279 pag.)WO2017/223229; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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. 2302-25-2

Step 3: 4-Bromo-1 H-imidazole (Aldrich) (500 mg, 3.40 mmol) is charged in a round-bottom flask and dissolved in THF (10 ml_). 2-Bromoacetophenone (Aldrich) (1 .35 g, 6.80 mmol, 2.00 eq) and potassium carbonate (940 mg, 6.80 mmol, 2.00 eq) are added. The reaction mixture is stirred for 16 h at RT, diluted with EtOAc and washed with water. The organic layer is dried over MgS04, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (100 % hexanes to 50 % EtOAc in hexanes) to provide intermediate 4044C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2302-25-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

54624-57-6, A common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Tri-tert-butylphosphine (4.4 mL of 1.0 M in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (22.8 g, 238 mmol)A solution of 2-bromo-1H-benzimidazole (36.0 g, 183 mmol) and p-methoxybromobenzene (35.0 g, 187 mmol) in degassed toluene (1 L) was added and the mixture was heated under reflux 2 hour.The reaction mixture was cooled to room temperature, diluted with toluene and filtered over EtOAc.The filtrate was diluted with water and extracted with toluene and the organic phases were combined and evaporated in vacuo.The residue was filtered through silica gel and recrystallized.Compound a (44.2 g, yield 80percent) was obtained.

The synthetic route of 54624-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Liu Xiqing; Cai Hui; (35 pag.)CN108218787; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, 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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below.

Compound 216; 1 -(1 H-Benzoimidazol-5-yl)-4-benzylimino-5-(4-bromo-phenyl)- imidazolidin-2-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) and 4-Bromobenzaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours 2ml of a solution of KOCN (KSCN) (2mmol) and Pyridinehydrochloride (2mmol) in MeOH is added was added. Finally 3- Benzylisocyanide (1 mmol) is added. The reaction was stirred at room temperature for 48h. After evaporation of the solvent the residue was purified with chromatographic methods. Yield: 0.230 g (50 %); mp: 244C, 1H-NMR (500 MHz, DMSO-D6): 4.46 (t, 3J=5.1 Hz, 2 H, CH2), 6.18 (s, 1 H, CH-N), 7.17 (m, 8 H, Ar), 7.39 (d, 3J=8.7 Hz, 1 H, Benzimid), 7.48 (dd, 3J=6.6 Hz, 4J=1.9 Hz, 2 H, Ar), 7.67 (s, br., 1 H, NH), 8.08 (s, 1 H, Benzimid), 8.67 (t, 1 H, Ar), 12.36 (s, br., 1 H, NH). . MS m/z 460.3 (M+H)+, HPLC (254 nm): rt 2.86 min (100 %)molecular weight (g/mol): 460.34 IC50 hQC (nM): 22

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; PROBIODRUG AG; WO2008/55947; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4331-29-7, Adding some certain compound to certain chemical reactions, such as: 4331-29-7, name is 1H-Benzo[d]imidazol-7-amine, 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 4331-29-7.

[00153] IC491791: 2-[l-(4-Amino-benzoimidazol-l-yl)-ethyl]-3-phenyl-3H- thieno[3,2-d]pyrimidin-4-one.; To a solution of 2-(l-Amino-ethyl)-3-phenyl-3H- thieno[3,2-d]pyrimidin-4-one (47 mg, 0.162 mmol) in DMF was added adenine (26 mg, 0.194), followed by the addition of potassium carbonate (22 mg, 0.162 mmol). The resulting mixture was then heated to 125¡ãC in an oil bath for 5 min. The reaction mixture was then cooled to room temperature, then treated with H2O (10 mL) to afford a precipitate. The precipitate was collected and dried in a vacuum oven to afford the crude product. Purification by HPLC (C- 18 Luna column 250 x 21.20 mm, 10-20percent CH3CN/H20 containing 0.05percent CF3CO2H) product was obtained as a fluffy white solid after lyophilizing: 1H NMR (400 MHz, DMSO-d6) delta 8.37 (s, IH), 8.25 (d, / = 5.2 Hz, IH), 8.16 (s, IH), 7.67 (d, / = 8.0 Hz, IH), 7.58 (m, IH), 7.44 (m, 2H), 7.36 (m, IH), 7.17 (d, / = 8.0 Hz, IH), 5.49 (q, / = 6.8 Hz, IH), 1.75 (d, J = 6.4 Hz, 3H). LC/MS (AP-ESI, CH3CO2H 0.05percent) m/z 390 (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 4331-29-7.

Reference:
Patent; ELI LILLY & CO.; WO2008/64018; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15813-09-9, Adding a certain compound to certain chemical reactions, such as: 15813-09-9, name is 4,5-Diiodo-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 15813-09-9.

Preparation 71 4-iodo-1H-imidazole To a solution of 4,5-diiodo-1H-imidazole (Preparation 70, 7.7 g, 24 mmol) in ethanol (80 ml) and water (20 ml) was added solid sodium sulfite heptahydrate (20 g, 79 mmol). The reaction mixture was heated at reflux for 16 h, cooled, and the solid by-products were removed by filtration. The filtrate was then concentrated in vacuo and the resultant solid was dnred by suction. The crude residue was recrvstallised from dichloromethane to give the title compound as a white solid (4.6 g, 64%). NMR (CDCl3, selected data for the free base: 7.0 (s 1H), 7.5 (s, 1H). MS (TSP): M/Z (MH+): 195.2; C3H3129IN2+H requires 194.9.

According to the analysis of related databases, 15813-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer INC; US6313312; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 288-32-4, name is 1H-Imidazole, I believe this compound will play a more active role in future production and life. 288-32-4

Compound XIII (880g, 12.9mol, 1.0eq.) In the autoclave 50L, 12L DMF were dissolved, cooled To below 0 ¡ãC, triethylamine (1308g, 12.9mol, 1.0eq. ) The reaction was kept 30min, 0 ¡ã C solution of the following threePhenyl chloride (3605.0g, 12.9mol, 1.0eq. ) In DMF (16L), drops Bi, 15 ¡ã C overnight with stirring 16 h. Thereaction mixture was poured into water, large amount of solid precipitated, suction filtered, the filter cake washedwith water, drained, dried to obtain compound XIV-1 White The solid 3835.1g, Yield: 95.6percent.

The chemical industry reduces the impact on the environment during synthesis 288-32-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PharmaBlock Sciences (Nanjing), Inc.; MAO, JUN; ZHU, JINGWEI; SHU, QINGNING; ZHAO, SHUHAI; YANG, MINMIN; WU, XIHAN; (14 pag.)CN104086553; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem