Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-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 71759-89-2, Recommanded Product: 5-Iodo-1H-imidazole

Step 1:To a 000 mixture of 4-iodoimidazole AlOa (5.0 g, 25.8 mmol) (Synthonix) in anhydrous THF (100 mL) is added NaH (60% in oil, 1 .24 g, 30.9 mmol). The resulting mixture is stirred for 10 mm before the addition of 4-methoxybenzyl chloride (4.37 mL, 32.2 mmol) (Aldrich). This mixture is allowed to warm to RT and is stirred overnight. An aqueous solution of saturated NH4CI (50 mL) is added and this mixture is stirred for 10 mm. The mixture is extracted with EtOAc (3x) and the layers are separated. The organic layer is washed with water and brine, dried with Mg504 and concentrated to provide crude material that is purified by Combif lash (20:80 to 80:20, EtOAc/hexanes) to provide AlOb.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Iodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; BILODEAU, Francois; POIRIER, Maude; PARISIEN, Mathieu; KUHN, Cyrille; THIBEAULT, Carl; TRINH, Thao; WO2014/70978; (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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Step 2: Intermediate 34-c To a solution of (l-methyl-lH-imidazol-5-yl) methanol (3.1 g, 27.6 mmol) and intermediate 34-b (4.01 g, 23.04 mmol) in toluene (25.0 ml) and DMPU (25.0 ml) was added sodium 2-methylpropan-2-olate (4.43 g, 46.1 mmol). The reaction was stirred overnight at 80 °C and then cooled to room temperature. A saturated aqueous solution of ammonium chloride and ethyl acetate were added, the organic layer was separated, washed twice with a saturated aqueous solution of ammonium chloride and brine, dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 34-c as beige 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; PHARMASCIENCE, INC.; LAURENT, Alain; ROSE, Yannick; JAQUITH, James B.; WO2013/177668; (2013); A1;,
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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1,2-dimethyl-1H-imidazole

General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

According to the analysis of related databases, 24134-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15469-97-3, These common heterocyclic compound, 15469-97-3, name is 1-Trityl-1H-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.

2-CARBOMETHOXY-1-TRITYLIMIDAZOLE To a stirred solution of 12.4 g (40 mmol.) of 1-tritylimidazole in 250 mL of tetrahydrofuran, under argon, at 0° C. was added 20 mL (48 mmol.) of a solution of n-butyl-lithium in hexane. After the solution was allowed to warm to ambient temperature, it was stirred for 1 hour and then 3.4 mL (50 mmol.) of methyl chloroformate was added dropwise. The mixture was stirred for 20 hours at 25° C., 100 mL of water was added and then the mixture was concentrated in vacuo. The residue was extracted with ether. After the extracts were dried (MgSO4) and concentrated, the residue was chromatographed on 200 g of silica using 1:3 ethyl acetate: hexane, followed by 1:1 ethyl acetate: hexane, and finally ethyl acetate to give 3.2 g of colorless product.

The synthetic route of 15469-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Marion Merrell Dow Inc.; US5039691; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-50-2, name is Imidazole-4-carbaldehyde, 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. Quality Control of Imidazole-4-carbaldehyde

Intermediate 18:l-trityl-lH-imidazole-4-carbaldehyde[00417 ] Triethylamine (3.05 ml, 21.86 mmol) was added to a solution of lH-imidazole-4- carbaldehyde (2 g, 20.82 mmol) and triphenylmethyl chloride (5.80 g, 20.82 mmol) in N5N- dimethylformamide (20 ml). The reaction mixture was stirred at room temperature for 18 hours. The crude mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The organic phase was washed dried over sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallised from dichloromethane and hexanes to afford the title compound as a cream solid (4.7 g, 67% yield).[00418] 1H NMR (DMSO-d6, 400 MHz) delta 7.10-7.16 (6H, m), 7.36-7.57 (9H, m), 7.63 (IH, s), 7.64 (IH, s), 9.91 (IH, s).

The synthetic route of 3034-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/94992; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7720-39-0, name is 1H-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 7720-39-0, Quality Control of 1H-Imidazol-2-amine

Example 19 5-(S)-Thioacetamidomethyl-3-[4′-(imidazole-2″-yl)aminocarbonyl-3′-fluoro-phenyl]-oxazolidine-2-one A solution of 5-(S)-thioacetamidomethyl-3-[4′-(pentafluorophenoxy)carbonyl-3′-fluorophenyl]oxazolidine-2-one (0.162 g, 0.34 mmol) and 2-aminoimidazole (0.083 mg, 1.0 mmol) in THF (5.0 mL) was stirred at r.t. for 0.5 h and then at 45 C. overnight. Solvent was removed under vacuum and the residue purified by PTLC (10% MeOH in DCM) to give the pure product as a white solid (0.058 g, 45%). MS (m/z): [M+H]+=378.

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; Pharmacia & Upjohn Company; US6441005; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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. category: imidazoles-derivatives

4-Cyanoimidazole (2.4 g, 25.9 mmol), KF-alumina (8 g), and iodomethane (15 mL, 240 mmol) were mixed and stirred at room temperature for 24 hours. After adding acetone (45 mL), it is stirred for 30 minutes and the solid is filtered off. After collecting the filtrate and blowing the solvent, the organic layer obtained by extraction with ethyl acetate and water is dehydrated with sodium sulfate, the solid is filtered off and the organic solvent is blown off. The reaction mixture was purified using silica gel column chromatography to obtain compound (3) (1.9 g, 17.7 mmol)This is obtained in 30% yield.

The synthetic route of 1H-Imidazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co., Ltd.; Cheil Industries Inc.; Pusan National University Institute for Research & Industry Cooperation; Noh Chang-ho; Yoon Ung-chan; Kwon O-hyeon; Choi Byeong-gi; (23 pag.)KR102046153; (2019); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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. Computed Properties of C4H3F3N2

To a solution of a tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (0.5 g, 1.8 mmol, CASRN: 15 8407-04-6) in dry DMF (4 mL) was added 4-(trifluoromethyl)-1H-imidazole (293 mg,2.16 mmol) and Cs2CO3 (1.17 g, 3.59 mmol). The reaction mixture was then stirred at 80 C for14 h. Insolubles were removed by filtration, and the filtrate was concentrated in vacuo. Thecrude residue was suspended in DCM and filtered through a pad of Celite to give a yellow oil,which was purified by flash chromatography with a 5i02 column, using an eluent mixture of nheptane and EtOAc (10% to 90%). This yielded the first fraction (301 mg) of the desired product as a colorless oil, and a second fraction (261 mg) of a mixture of the desired product with impurities. The second fraction was submitted for SFC purification, and the purified product was combined with the first fraction to yield 430 mg of the desired product as a colorless oil. MS(ESI): m/z = 334.2 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33468-69-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ANSELM, Lilli; BENZ, Joerg; GRETHER, Uwe; GROEBKE ZBINDEN, Katrin; HEER, Dominik; HORNSPERGER, Benoit; KROLL, Carsten; KUHN, Bernd; O`HARA, Fionn; RICHTER, Hans; (268 pag.)WO2020/35425; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10394-38-4, 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. 10394-38-4, name is 1-Methylbenzoimidazol-5-amine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

12.5 N-(1-methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide; 0.18 g (1.23 mmol) of 5-amino-1-methylbenzimidazole and 10 ml of dry toluene are placed, while flushing with nitrogen, in a 100 ml three-necked flask cooled to 0 C. and equipped with a magnetic stirrer. To this solution is then added slowly 0.95 ml (1.90 mmol) of a 2M solution of trimethylaluminum in toluene. The reaction mixture obtained is maintained under a nitrogen atmosphere and stirred, while allowing the temperature to rise gradually to 70 C. A solution of 0.3 g (0.95 mmol) of product obtained in step 12.4 in 10 ml of dry toluene is then added dropwise over 5 minutes using an addition funnel. The reaction mixture is then refluxed for 5 hours and stirred at room temperature overnight. 20 ml of cold water are then added to the solution cooled to 0 C., followed by addition of 10 ml of 1N hydrochloric acid. After stirring for 1 hour, the precipitate is recovered by filtration, rinsed with water and dried under reduced pressure. 0.22 g (0.53 mmol) of the expected product is obtained in the form of a white solid.Melting point: 266-268 C.1H NMR (DMSO D6), delta (ppm): 9.5 (s, 1H); 8.5 (s, 1H); 7.9 (s, 2H); 7.5 (m, 3H); 7.3-6.8 (m, 5H); 5.9 (s, 2H); 3.95 (s, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Methylbenzoimidazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2008/125459; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1977-72-6, 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. 1977-72-6, name is 5-Fluoro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-fluoro-1H-benzoimidazole (0.50 g, 0.00367 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60percent dispersion in oil, 0.44 g, 0.011 mol). After addition, the resulting mixture was stirred for 2 h. (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide (1.29 g, 0.00367 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at room temperature under argon. The reaction was quenched by water, extracted with ethyl acetate. The organic layer was dried with MgSO4, filtered, and concentrated under vacuum. The product was purified by a silicon gel column using methylene chloride and methanol (19:1) as eluent to afford 0.17 g of the desired compound as white solid. 1H NMR (400 MHz, DMSO-d6)^10.37 (s, 1H, NH), 8.31 (d, J = 17.2 Hz, 1H, ArH), 8.16-8.05 (m, 3H, ArH), 7.62-7.56 (m, 1H, ArH), 7.44 (dd, J = 9.60 Hz, J = 2.4 Hz, 1H, ArH), 7.04 (dd, J = 9.60 Hz, J = 2.4 Hz, 1H, ArH), 6.49 (s, 1H, OH), 4.65 (d, J = 5.6 Hz, 1H, CH), 4.62 (d, J = 5.6 Hz, 1H, CH), 1.47 (s, 3H, CH3). Mass (ESI, Negative): 404.8[M-H]-; (ESI, Positive): 429.0[M+Na]+.

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

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; PAGADALA, Jayaprakash; DUKE, Charles B.; COSS, Christopher C.; DALTON, James T.; (296 pag.)WO2016/172358; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem