Category: imidazoles-derivatives

Reference of 24134-09-6, These common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-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.

A mixture of {3-chloro-5-[(methyloxy)carbonyl]phenyl}boronic acid (1.703 g, 7.94 mmol), 4-bromo-1 ,2-dimethyl-1 H-imidazole (D37a, 1.1 12 g, 6.35 mmol) and 5- bromo-1 ,2-dimethyl-1 H-imidazole (D37b, 222 mg, 1.271 mmol) as an isomeric mixture, sodium carbonate (1.347 g, 12.71 mmol) and bis(triphenylphosphine)palladium(ll) dichloride (446 mg, 0.635 mmol) in toluene (10 ml.) and ethanol (1 ml.) was stirred under reflux overnight. The reaction mixture was partitioned between dichloromethane and water and the layers separated. The aqueous layer was extracted with dichloromethane (x2) and the combined organic layers were dried (magnesium sulfate) and concentrated. The residue was acidified and purified using SCX chromatography, eluting with methanol then 2N ammonia in methanol. The basic fractions were combined and concentrated to leave the crude mixture of title compounds which was used without further purification. LC/MS (ES+ve): [M+H]+ 265, 267 (Ci3H13CIN2O2 requires [M+H]+ 265, 267)

The synthetic route of 24134-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/819; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 716-79-0, 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. 716-79-0 name is 2-Phenyl-1H-benzo[d]imidazole, 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.

General procedure: To the reaction vessel containing benzimidazole or imidazole (1mmol), alkyl halide (1mmol), 50percent NaOH (0.5mL) and anionic surfactant sodium dodecyl sulfate (5molpercent) was added and the reaction mixture was vigorously stirred at room temperature or 60°C. After the completion of reaction (TLC) followed by standard workup using ethyl acetate as extracting solvent the crude product was purified over silica-gel (60?120 mesh) using ethyl acetate?hexane (3:7) as eluent to afford pure products. Identities of the products were judged by the comparison of melting point, IR data, 1H NMR, 13C NMR and HRMS analyses.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Article; Chakraborty, Ankita; Debnath, Sudipto; Ghosh, Tanmoy; Maiti, Dilip K.; Majumdar, Swapan; Tetrahedron; vol. 74; 40; (2018); p. 5932 – 5941;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1402838-08-7, 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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-(2-chlorobenzofuran-5-yl)ethane-1-one (0506-157) (120 g, 0.61 mmol, 1.0 equiv) and2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (380 mg, 0.92 mmol, 1.5 equiv)Dissolved in 10 ml dioxaneAdd 1 ml concentrated sulfuric acid dropwise to the ice bath.The temperature was raised to 90C and the reaction was stirred for 18 hours.Cool to room temperature and add dropwise to ice water. Under ice bath, add sodium hydroxide to adjust pH>8, extract with ethyl acetate, separate, spin dry, and purify the crude product with silica gel column chromatography (eluent: Dichloromethane/methanol = 200/1 to 40/1) gives the product1-(2-Chlorobenzofuran-5-yl)-2-(5H-imidazo[5,1-a]isoindoline-5-yl)ethane-1-one (100 mg, 46.5%) .

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, 2-(1-Trityl-4-imidazolyl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 29043-48-9,Some common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, molecular formula is C8H9N3, 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.

General procedure: Example 2C 5-methyl-N-(2-methyl-2H-indazol-5-yl)-4-oxo-4,5,6,7-tetrahydrofuro[3,2-c]pyridine-3-carboxamide To a solution of the product from Example 2B (0.1 g, 0.512 mmol) in N,N-dimethylformamide (4 mL) was added 2-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (0.195 g, 0.512 mmol) and triethylamine (0.071 mL, 0.512 mmol). After mixing, 2-methyl-2H-indazol-5-amine (0.075 g, 0.512 mmol) was added, and the vial was shaken for 4 hours. The mixture was concentrated and triturated with methanol to provide the titled compound. 1H NMR (DMSO-d6) delta ppm 12.76 (s, 1H), 8.32 (s, 1H), 8.29 (s, 1H), 8.25 (d, J=4 Hz, 1H), 7.60 (d, J=12 Hz, 1H), 7.29 (d, J=12 Hz, 1H), 4.41 (s, 3H), 3.75 (t, J=8 Hz, 2H), 3.11 (t, J=8 Hz, 2H), 3.06 (s, 3H); MS (ESI) m/z 325 (M+H)+.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Altenbach, Robert J.; Liu, Huaqing; Clapham, Bruce; Aguirre, Ana L.; Cowart, Marlon; Koenig, John R.; Sarris, Kathy; Scanio, Marc J.; Swinger, Kerren K.; Vasudevan, Anil; Villamil, Clara I.; Woller, Kevin R.; (95 pag.)US9777020; (2017); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20075-26-7, A common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, molecular formula is C5H8N2O, 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.

A. Preparation of 1-(methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol. A butyllithium solution, prepared from 1.02 g. (0.145 g. at.) of lithium and 7.9 g. (0.058 mol) of butyl bromide in 70 ml. of anhydrous diethyl ether, was added drop-wise at -60 C. to -65 C. under a nitrogen atmosphere to a solution of 4.9 g. (0.044 mol) of 1-(methoxymethyl)imidazole and 3.1 g. (0.044 mol) of N,N,N’,N’-tetramethylethylenediamine in 125 ml. of anhydrous tetrahydrofuran. The reaction mixture was kept standing for 2 hours at -60 to -65 C. and then 11 g. (0.044 mol) of 4-(trifluoromethyl)benzophenone, dissolved in 75 ml. of anhydrous tetrahydrofuran, were added drop-wise. The temperature was maintained at -65 C. for one hour and then the reaction mixture was allowed to attain room temperature overnight. 10 ml. of water and solid carbon dioxide were added and the solvent was distilled off. The residue was dissolved in dilute hydrochloric acid, the solution was washed with diethyl ether and made alkaline with potassium carbonate. The solid substance formed was filtered off and dissolved in chloroform. The solution was washed with water, dried over sodium sulphate and concentrated by evaporation of the solvent. The residue was crystallized from isopropyl alcohol. 1-(Methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol was obtained. Melting point 158-159 C.

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; Gist-Brocades N.V.; US4152441; (1979); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 2302-25-2, name is 4-Bromo-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. SDS of cas: 2302-25-2

A mixture of 4-bromo-imidazole (217 mg, 1.48 mmol) and cesium carbonate (875 mg, 2.69 mmol) in dimethylformamide (5 mL) was stirred for 30 minutes. 4-(2-Chloro-ethyl)-morpholine hydrochloride (250 mg, 1.34 mmol) was added and the mixture was heated to 50C. After heating overnight the reaction was concentrated by rotary evaporation. The residue was suspended in a mixture of dichloromethane andmethanol and filtered. The filtrate was concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, methanol to afford 4-[2-(4-Bromo-imidazol-1-yl)-ethyl]-morpholine (148 mg, 42%).

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

Reference:
Patent; PFIZER INC.; WO2006/21886; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]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. category: imidazoles-derivatives

General procedure: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

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

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-70-0, The chemical industry reduces the impact on the environment during synthesis 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, I believe this compound will play a more active role in future production and life.

l-(4-Ethynyl-2-methoxyphenyl)-l//-imidazole.A mixture of 4-fiuoro-3-methoxybenzaldehyde (1.0 g, 6.5 mmol) in 20 mL of DMF was treated with 4-methylimidazole (1.0 g, 15 mmol) and warmed to 130 C. Stirred overnight. Diluted with EtOAc, washed with sat’d NaHCO3, dried (Na2SO4), concentrated. Dissolved in 20 mL of MeOH, treated with K2CO3 (2.0 g, 14 mmol) and dimethyl (l-diazo-2-oxopropyl)phosphonate (1.5 g, 7.8 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), cone. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne:1H NMR (600 MHz, CDCl3) delta7.79 (s, 1 H), 7.18 (t, J= 1.2 Hz, 1 H), 7.16 (d, J= 1.8 Hz, 1 H), 7.15 (m, 2 H), 7.13 (d, J= 1.5 Hz, 1 H).

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, 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2008/156580; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 57090-88-7, A common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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 round bottom flask was added NaH (60percent in mineral oil) (200 mg, 5.22 mmol) in dry THF (12 ml), followed by the addtion of 1H-imidazole-4-carbonitrile (400 mg, 4.3 mmol), SEMCl (1433 mg, 8.6 mmol). The reactiom mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtO Ac/sat. NaHCO3. The organic phase was separated, washed with water, brine, dried over anhy. Na2SO4, filtered and concentrated. The resulting residue was purified by flash chromatography on silica gel (0-3percent MeOH/CH2Cl2). The product fractions were collected and concentrated to afford 355 mg of 1-(2-trimethylsilanyl- ethoxymethyl)-1H-imidazole-4-carbonitrile, m/z 224.6 [M+l]+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); 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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4N2O

Example 72An alternate method’for the synthesis of the imidazole intermediate is described below:4-Cyano-l-(2-trimethylsilanyl-ethoxymethyl)-lH-imidazole-2-carboxylic acid potassium salt a) lH-Imidazole-4-carbonitrile; ‘-NHA 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, a condenser, and an addition funnel with a nitrogen inlet was charged with lH-imidazole-4-carboxaldehyde (Aldrich, 1.10 kg, 11.5 mol) and pyridine (3.0 L, 3.0 mol). The reaction flask was cooled to 8 0C with an ice bath and hydroxylamine hydrochloride (871 g, 12.5 mol) was added slowly in portions to maintain the internal temperature below 30 C. The reaction was allowed to cool to ambient temperature and stirred for 2 h at ambient temperature. The resulting thick yellow solution was heated to 80 0C with a heating mantle and acetic anhydride (2.04 L, 21.6 mol) was added dropwise EPO over 200 min to maintain the temperature below 110 C during the addition. The reaction mixture was heated at 100 0C for 30 min, after which time it was allowed to cool to ambient temperature and then further cooled in an ice bath. The pH was adjusted to 8.0 (pH meter) by the addition of 25 wt % NaOH (5.5 L) at such a rate that the internal temperature was maintained below 30 C. The reaction mixture was then transferred into a 22-L separatory funnel and extracted with ethyl acetate (6.0 L). The combined organic layer was washed with brine (2 x 4.0 L), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure at 35 C to give the crude product as a yellow semisolid. The resulting semisolid was suspended in toluene (3.0 L) and stirred for 1 h, after which time it was filtered to give a light yellow solid, which was resuspended in toluene (3.0 L) and stirred for 1 h. The resulting slurry was filtered and the filter cake washed with toluene (2 x 500 mL) to give the title compound as a light yellow solid [870 g, 82%). The 1H and 13C NMR spectra were consistent with the assigned structure.

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; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem