Month: June 2021

Synthetic Route of 3034-50-2, A common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 1L three-necked round-bottomed flask with an addition funnel was added 3H-imidazole-4-carbaldehyde (4, 12 g, 0.125 mol) trityl chloride (38.3 g, 0.137 mol) and acetonitrile (400 mL). The mixture was stirred at rt to give a slurry. Triethylamine (30 mL, 0.215 mol) was added drop wise over 20 min. After the addition was complete, the reaction mixture was stirred at rt for 20 h. Hexane (40 mL) and water (400mL) were added. The slurry was stirred for 30 min and filtered. The cake was washed with water (3 × 100 mL) and dried in a vacuum oven at 50 C for 20 h to give 5 as a white solid (39.8 g, 94%).

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; Suryadevara, Praveen Kumar; Racherla, Kishore Kumar; Olepu, Srinivas; Norcross, Neil R.; Tatipaka, Hari Babu; Arif, Jennifer A.; Planer, Joseph D.; Lepesheva, Galina I.; Verlinde, Christophe L.M.J.; Buckner, Frederick S.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 23; (2013); p. 6492 – 6499;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-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. Recommanded Product: 2-Bromo-1-methyl-1H-imidazole

The 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid used in the method described above was prepared as follows: (i) To a stirred solution of 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate (0.200 g, 1.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 2-bromo-1-methyl-1 H-imidazole (0.146 ml, 1.500 mmol) in 1 ,4-dioxane (8 ml) was added potassium phosphate (1.062 g, 5.00 mmol), copper(l) iodide (0.190 g, 1.000 mmol) and trans-N,N-dimethylcyclohexane-1 ,2- diamine (0.155 ml, 1.000 mmol) and the mixture heated at reflux under argon overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The solid was filtered off, washed with dichloromethane and the filtrate reduced under vacuum. The residue was re-dissolved in dichloromethane and washed with 0.880 ammonia solution (x2), water then brine and passed through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by Flashmaster automated silica gel chromatography eluting with 0-10% methanol in dichloromethane to give 1 ,1-dimethylethyl 3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylate (145 mg, 37.8 % yield). LC/MS[M+H]+ = 281.

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Application In Synthesis of 1-Methyl-1H-imidazole-5-carbaldehyde

To a cloudy mixture of 6-bromo-2,4-dichloro-3-phenylquinoline (290.5 mg, 0.823 mmol, Intermediate 1: step c) and 1-methyl-1H-imidazole-5-carbaldehyde (90.6 mg, 0.823 mmol) in THF (8 mL) under nitrogen at -78 C. was added n-BuLi (1.6 M in hexane, 0.643 mL, 1.03 mmol) dropwise. The resulting solution was stirred at -78 C. for 3 hours, then was warmed to 0 C. for 15 minutes before addition of saturated aqueous NH4Cl to quench. The mixture was diluted with water and was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-6% MeOH-DCM) to afford the title compound as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39021-62-0, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; (53 pag.)US2017/258782; (2017); 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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

To a solution of chloride 2 (scheme 1) (2.45 g, 14.4 mmol) in THF (48 mL) at -78C was slowly added w-BuLi (2.5M in hexane, 7.2 mL, 18.0 mmol). The reaction mixturewas stirred for one hour [at -78C] followed by slow addition of ZnCl (0.5M in THF, 36mL, 18.0 mmol). In a few minutes the reaction mixture was allowed to warm to roomtemperature and stirred for one hour.[0422] A solution of 4-iodo-l -methyl- 1/f-imidazole (1.50 g, 7.2 mmol) Tet. Lett. 2004.45. 5529] in THF (5 mL) and the tetrakis(triphenylphosphine) palladium (0) (0.83 g, 0.72mmol) were added to the reaction mixture which was heated to reflux for 1 hour, cooled toroom temperature, diluted with aqueous ammonium hydroxide and, finally neutralized witha IN HC1 solution. The acidic solution was extracted with DCM, the extract was washedwith water and brine, dried over anhydrous magnesium sulfate, filtered and evaporatedunder reduced pressure. The residue was purified by flash chromatography (eluents DCM,then DCM-MeOH, 97:3) to afford title compound 175 (1.45 g, 81% yield) as a yellow solid.LRMS (M+l) 263.9 (100%), 265.9 (33%).

According to the analysis of related databases, 71759-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; METHYLGENE, INC.; WO2006/10264; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 6160-65-2, 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows.

After performing this reaction several times, all product fractions were pooled and the resulting residue of the dihydroxyl derivative (124 mg, 269 mumol, 1 eq.) was dissolved under argon in tetrahydrofurane (80 mL) in a 250 mL flame-dried flask. To this solution was added thiocarbonyl diimidazole (480 mg, 2.69 mmol, 10 eq.) and 4-(dimethylamino)pyridine (329 mg, 2.69 mmol, 10 eq.). The resulting reaction mixture was heated to 80C and stirred at this temperature overnight. After cooling to room temperature, a small portion of silica gel was added and the solvent was removed under reduced pressure. The adsorbed crude product was purified by flash column chromatography (50% ethyl acetate in cyclohexane) to yield 119 mg (237 mumol, 88%) of (VII) as a colorless solid.

The chemical industry reduces the impact on the environment during synthesis 1,1′-Thiocarbonyldiimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; EP2210881; (2010); 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. 5465-29-2, name is 2-Propylbenzimidazole, A new synthetic method of this compound is introduced below., Safety of 2-Propylbenzimidazole

The 1H-benzo[d]imidazole 5a(2.50 mmol) was dissolved in 10 ml of abs. DMF. Sodium hydride(60% dispersion in mineral oil) (0.2 g, 5 mmol) was added withcooling. After the gas formation stopped, 40-bromomethyl-[1,10-biphenyl]-2-carbonitrile dissolved in 2 ml of abs. DMF was addeddropwise and the solutionwas stirred for 1 h under cooling in an icebath and further 2 h at RT. Water was added and after the solutionwas acidified with HCl, the product was extracted three times withmethylene chloride. The combined organic layers were dried overNa2SO4 and evaporated to dryness in vacuo. The crude product waspurified by column chromatography on silica gel with methylenechloride/methanol (95:5) and recrystallized from diethyl ether/methanol.

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Obermoser, Victoria; Urban, Margarethe E.; Murgueitio, Manuela S.; Wolber, Gerhard; Kintscher, Ulrich; Gust, Ronald; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 138 – 152;,
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. 15965-31-8, name is 5-Chloro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 15965-31-8

A stirred suspension of 4-chloro-lH-imidazole (9.75 mmol, 1.0 g) , 2-chloro-5-nitropyridine (9.75 mmol, 1.54 g) and potassium carbonate (11.70 mmol, 1.61 g) in DMF (10 mL) was heated at 80 C for 3 hours. The mixture was cooled to room temperature and water was added. The resulting precipitate was filtered, washed with water and dried to give crude 6- ( 4-chloroimidazol-l-yl ) -3- nitropyridine (1.94 g, 89%).

The synthetic route of 15965-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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 suspension of 0.351 g of imidazole-2-carboxylic acid (3.13 mmol) in 15 ml DMF were added 0.508 g of CDI (3.13 mmol) and 0.43 ml triethylamine (3.13 mmol), and the mixture stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (2.4 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and trying 0.42 g 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (57%) were obtained as a yellow solid; M.p.: 227-228 C.

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

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-13-3, 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 641571-13-3 as follows.

To a solution of 4-methyl-N3-[l-(7Eta-rhoyrrolo[2,3-J]pyrimidin-4-yl)-lEta- imidazol-2-yl] -benzene- 1,3 -diamine (15.0 mg, 0.049 mmol), 3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-benzoic acid (16.0 mg, 0.059 mmol), and DIEA (35yL, 0.20 mmol) in DMF (2mL) is added HATU (21 mg, 0.055 mmol). After stirring for 1 hour at room temperature, the solvent is removed under vacuum. The residue is dissolved in DMSO (ImL). The resulting solution is subjected to purification by reverse-phase HPLC to give 3-(4-methyl- EPO imidazol-l-yl)-N-{4-methyl-3-[l-(7H-pyrrolo[2,3-cT]pyrimidm-4-yl)-lH-imidazol-2- ylamino]-phenyl}-5-trifluoromethyI-benzamide: 1H NuMR 600 MHz (DMSO-J6) delta 12.73 (s, IH), 11.32 0, IH), 10.67 (s, 1 H), 9.60 (s, 1 H), 8.82 0,1 H), 8.64-8.56 (m, 2H), 8.46 (s, IH), 8.43 (s, IH), 8.17 (s, IH), 7.93 (d, IH, J= 2.8 Hz), 7.79 (t, IH, J= 3.2 Hz), 7.52 (d, IH, J= 8.0 Hz), 7.30 (J, IH, J= 8.0 Hz), 7.11 (s, IH), 7.07 (m, IH), 2.39 (s, 3H), 2.36 (5, 3H); MS m/z 558.2 (M + 1).

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2006/101783; (2006); A2;,
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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-1H-imidazole-4-sulfonyl chloride

Intermediate example 1-84 (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl l-methyl-lH-imidazole-4- sulfonateTo a solution of (35)-3-(dibenzylamino)chroman-5-ol (300 mg, 0.87 mmol, described in WO9914212A1) in acetonitrile (10 mL) was triethylamine (0.363 mL, 2.61 mmol) and 1- methyl-leta-imidazole-4-sulfonyl chloride (173 mg, 0.96 mmol) added and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was concentrated in vacuo and purified by column chromatography using a gradient of ethyl acetate in heptane to yield 375 mg (88 %); 1H NMR (400 MHz, DMSO-J6) delta ppm 8.06 (d, 1 H), 7.93 (d, 1 H), 7.30 – 7.42 (m, 8 H), 7.18 – 7.27 (m, 2 H), 7.06 (t, 1 H), 6.69 (dd, 1 H), 6.62 (dd, 1 H), 4.17 – 4.31 (m, 1 H), 3.97 (t, 1 H), 3.61 – 3.73 (m, 7 H), 2.84 – 2.99 (m, 2 H), 2.63 – 2.75 (m, 1 H); MS (ESI) m/z 490 [M+H+].

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 137049-00-4.

Reference:
Patent; ASTRAZENECA AB; WO2008/130319; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem