Category: imidazoles-derivatives

These common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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. Safety of 1H-Benzo[d]imidazole-2-carbaldehyde

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0°C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion using general procedure 3, 2-(2-aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-5-methyl- 1 ,3-thiazole-4-carboxamide dihydrochloride (113) (274 mg, 0.75 mmol), 1 H-1 ,3-benzodiazole-2- carbaldehyde (109 mg, 0.75 mmol), DIPEA (0.45 ml, 2.61 mmol) and anhydrous MgSQ (200 mg) in MeOH (10 ml) and DCM (10 ml) at room temperature for 20 h, followed by addition of NaB4 (60 mg, 1.48 mmol) afforded the title compound (140 mg, 44percent) as a pale yellow solid after purificatbn by prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.17 (s, 1 H), 8.59 (t, J = 5.6 Hz, 1 H), 8.36 (dt, J = 4.7, 1.4 Hz,1 H), 7.70 (ddd, J = 9.9, 8.4, 1 .1 Hz, 1 H), 7.53 (d, J = 7.5 Hz, 1 H), 7.44 (d, J = 7.5 Hz, 1 H), 7.40 (dt, J = 8.5, 4.4 Hz, 1 H), 7.13 (p, J = 6.6 Hz, 2H), 4.65 – 4.59 (m, 2H), 3.96 (s, 2H), 3.10 (t, J = 6.8 Hz, 2H), 2.94 (t, J = 6.8 Hz, 2H), 2.68 (s, 3H) HPLCMS (Method C): [m/z]: 425.2 [M+H]+

The synthetic route of 1H-Benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 15108-18-6,Some common heterocyclic compound, 15108-18-6, name is 2-Hydrazinyl-1H-benzo[d]imidazole, molecular formula is C7H8N4, 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 solution of 2-hydrazino-1 H-benzimidazole (5.0 g, 33.7 mmol) in ethanol (30 ml) is added sequentially triethylamine (5 ml, 33.7 mmol) and N-cyanoformimidic acid ethyl ester (3.3 g, 33.7 mmol) with cooling. After stirring for 2 hours at 0C the resulting precipitate is filtered with suction and dried to give 3-, amino-2-(1 H-benzimidazol-2-yl)-1, 2, 4-triazole. 1H- NMR (400 MHz, d6-DMSO) : 13.0 (s, 1 H) ; 7.77 (s, 1 H) ; 7.70 (m, 2H); 7.50 (m, 2H); 7.20 (s, 2H).

The synthetic route of 15108-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA AG; WO2005/77939; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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. Product Details of 144689-93-0

Example 3; Preparation of olmesartan medoxomilTo dimethyl acetamide (800 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (100 gms) and powdered potassium carbonate (200 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (300 gms) at 45-50C. The contents were stirred for 8-10 hours at 45-50C. The insolubles were filtered. The contents were cooled to 5-100C. Potassium tertiary butoxide (100 gms) was charged at a temperature below 45C. The reaction was maintained at 40-450C for 3 hrs. To this was slowly added 5-methyl-2-oxo-1 ,3-dioxane-4-yl) methyl chloride at 40-450C 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 acidified with hydrochloric acid (100 ml) slowly at 25-30C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-5C and was filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (500 ml), neutralized with base and extracted in dichloromethane (500 ml).The clear dichloromethane extract was then concentrated under reduced pressure, stripped off with acetone. The residue thus obtained was isolated from the acetone (250 ml) to give 55 gms of the title compound. Chromatogrphic purity- > 99%

The synthetic route of 144689-93-0 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

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. 3034-38-6, name is 5-Nitro-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H3N3O2

EXAMPLE 2 202 parts of 5-nitroimidazole is dissolved in 600 parts of formic acid (90% by weight), 250 parts of dimethyl sulfate is added and the whole is heated for 6 hours. The formic acid is distilled off in vacuo. 420 parts of water is added to the residue, the whole cooled to from 0 to 5 C. and the unreacted 5-nitroimidazole (60 parts) is centrifuged off. The mixture is adjusted to pH 10 with aqueous ammonia solution (25% by weight) and the precipitate is separated at 0 to 5 C. 130 parts of 1-methyl-5-nitroimidazole having a melting point of 58 to 60 C. is obtained; this is equivalent to a yield of 82% of theory based on reacted 4(5)-nitroimidazole.

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; BASF Aktiengesellschaft; US4021442; (1977); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, 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 939-70-8, name: 1-(1H-Benzo[d]imidazol-2-yl)ethanone

Synthesis of target compound Y-0: 2-acetylbenzimidazole (1 mmol) at 0 CTo a solution of ethanol (10 mL) was added 60% aqueous potassium hydroxide solution (3 mL) and benzaldehyde (1 mmol),Stir at room temperature until the reaction is complete. TLC monitors the progress of the reaction.After the reaction is complete, add crushed ice and dilute hydrochloric acid solution, adjust the pH to form a precipitate,The crude extract was dried by filtration and purified by column chromatography to obtain the target compound Y-0.(Synthesis method see literature: European Journal of Medicinal Chemistry 143 (2018) 66-84) Yield: 62.6%;

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; Lanzhou University; Liu Yingqian; Wang Renxuan; Li Juncai; Yang Chengjie; Chen Yongjia; Peng Jingwen; Yin Xiaodan; Yan Yinfang; (10 pag.)CN110839636; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, molecular formula is C4H4N2O, 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. COA of Formula: C4H4N2O

Example 1: Ethyl (2-formyl-1H-imidazol-1-yl)acetate To an N-methylpyrrolidone (25 mL) solution of 1H-imidazole-2-carbaldehyde (2.0 g), potassium carbonate (2.9 g) and ethyl chloroacetate (6.7 mL) were added. The resultant solution was stirred at room temperature for 6 hours. To the reaction solution, water (50 mL) was added. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration and then the organic solvent was conentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane : ethyl acetate = 60 : 40 ? 0 : 100) to obtain the title compound having the following physical properties (2.9 g). TLC: Rf 0.54 (dichloromethane: methanol : 28% ammonia water = 90 : 10 : 1); NMR(CDCl3): delta 1.30(t, J = 7.2 Hz, 3H), 4.25(q, J = 7.2 Hz, 2H), 5.14(s, 2H), 7.15(d, J = 0.9 Hz, 1H), 7.33(d, J = 0.9 Hz, 1H), 9.79(s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10111-08-7, its application will become more common.

Reference:
Patent; Ono Pharmaceutical Co., Ltd.; EP2055705; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1964-77-8, A common heterocyclic compound, 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole, molecular formula is C8H7BrN2, 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 1 :[00224] To 5-bromo-2-methylbenzimidazole (38 g, 180 mmol) in THF (400 mL) was added di-/ert-butyl dicarbonate (39 g, 189 mmol). The reaction mixture was stirred at room temperature for 24 h and then concentrated. Ethyl acetate (400 mL) was added to the residue, and the solution was washed with 10% aqueous citric acid (2 x 100 mL), water (100 mL), and brine (100 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (gradient 20-30% ethyl acetate in hexane) provided 1 , 1 -dimethylethyl 6-bromo-2- methyl- lH-benzimidazoie-l -carboxylate (27 g, 48% yield) as a beige solid. MS (EI) for Ci3H,5BrN202: 312 (MH+).

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; EXELIXIS, INC.; RICE, Kenneth; WO2012/71501; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7098-07-9, name is 1-Ethyl-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 7098-07-9, SDS of cas: 7098-07-9

General procedure: A solution of N-alkylimidazole (10 mmol, 2 equivalents) and Dibromoalkane (5 mmol, 1 equivalent) was refluxed in toluene (20 mL) for 24?30 h. The reaction mixture was allowed to cool and toluene was decanted leaving a sticky solid behind. The sticky solid was washed three times with dry THF and finally with diethyl ether once. Solvent was removed under vacuum to get a white amorphous hygroscopic powder (88?94 percent yield). NMR spectra were recorded in D2O and/or DMSO-d6.

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; Aher, Sainath Babaji; Bhagat, Pundlik Rambhau; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5587 – 5596;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33016-47-6, 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 33016-47-6 as follows.

E (R)-N-[1-(Phenylmethyl)-4-[1-(triphenylmethyl)-1H-imidazol-4-yl]-3-butenyl]benzenesulfonamide A solution of compound D (400 mg, 0.63 mmol) and 1-trityl-4-formylimidazole (320 mg, 0.94 mmol) in methylene chloride was dried over MgSO4. The solids were filtered and the filtrate evaporated to dryness. The white foam residue was diluted with of THF (24 mL) and 3A molecular sieves added. After 1 hour, a solution of lithium bis(trimethylsilyl)amide (1.4 mL, 1M) in THF was added dropwise. After 1 hour, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate and the solution washed with brine, dried (MgSO4) and concentrated. The resulting residue was purified by flash chromatography on silica gel. Elution with 40% ethyl acetate in hexane afforded (108 mg) of the title compound, and (149 mg) of the Z-isomer (Combined yield 67%). MS; (M+H)+=610.

According to the analysis of related databases, 33016-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US6387926; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 28890-99-5, These common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, 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.

Intermediate compound 1: (E)- 1 ,3-dibromo-2-(4- methoxystyryl)benzene is synthesized starting from the formation of phosphonium salt with 1,3-dibromo-2-(bromom- ethyl)benzene and triphenylphosphine, followed by Wittig olefination with 4-methoxybenzaldehyde. 1 then undergoes hydrogenation to afford 1 ,3-dibromo-2-(4-methoxyphen- ethyl)benzene, whereby the methoxy sub stituent is deprotected to give phenol derivative intermediate compound 2. Intermediate compound 2 is treated with standard palladium catalyzed reaction conditions to form diaryl ether 3 from intramolecular C-O cross-coupling using known methods (Journal of the American Chemical Society 2011, 133, 9282-92 85, which is incorporated by reference herein in its entirety). 3, together with 1 ,3-dibromobenzene and dichlorodiphenylsilane, undergoes lithiation with n-butyllithium to afford intermediate compound 4. Inventive host compound 5 is then synthesized by a cross-coupling reaction between4 and 5H-benzo[d]benzo[4,5]imidazo[1 ,2-a]imidazole under standard l3uchwald-Hartwig amination reaction conditions.

Statistics shows that 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole is playing an increasingly important role. we look forward to future research findings about 28890-99-5.

Reference:
Patent; Universal Display Corporation; Wolohan, Peter; Drennan, Diana; Fitzgerald, George; (171 pag.)US2018/315942; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem