Category: imidazoles-derivatives

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. 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Formula: C9H11N3O

A mixture of 1.00 g (4.71 mmol) of ethyl (2-cyano-3-ethoxyprop-2-enoyl)carbamate (for preparation see: Senda, Shigeo, Hirota, Kosaku, Notani, Jiyoji; Chemical & Pharmaceutical Bulletin (1972), 20(7), 1380-8) and 835 mg (4.71 mmol) of 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-one in 5 ml of acetonitrile and 10 ml of DMF was stirred at reflux temperature overnight. After cooling to RT, the mixture was diluted with 150 ml of diethyl ether and the precipitate was filtered off. The filter residue was stirred with 10 ml of methanol, and the solid was filtered off, washed with a little methanol and ether and dried under high vacuum. This gave 703 mg (45% of theory) of the title compound. LC-MS (Method 1): Rt=0.53 min; m/z=298 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=3.30 (br. s, 3H), 3.36 (br. s, 3H), 7.17 (dd, 1H), 7.23-7.28 (m, 1H), 7.34 (d, 1H), 8.77 (s, 1H).

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; Bayer Pharma Aktiengesellschaft; Furstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Zubov, Dmitry; Schamberger, Jens; (69 pag.)US2016/244415; (2016); A1;,
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Related Products of 570-22-9, These common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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.

General procedure: 10 mL ethanol solution of 2.0 mmol metal salt was added into 10 mL ethanol solution of 2.0 mmol 4,5-imidazole dicarboxylic acid. Having blended the mixture under reflux for 1 h, methanol solution of 1.0 mmol NaOH was put into hot mixture drop by drop. After 5 h under reflux, solvent of the solution was removed, precipitate was filtered. The precipitates were washed with methanol 3 times and dried in 105 C. Molecular structures of complexes obtained from the reaction of 4,5-imidazole dicarboxylic acid ligand with metal salts were summarized in Fig. 2.1.

Statistics shows that 1H-Imidazole-4,5-dicarboxylic acid is playing an increasingly important role. we look forward to future research findings about 570-22-9.

Reference:
Article; Erdem, Ozlem; Yildiz, Emel; Inorganica Chimica Acta; vol. 438; (2015); p. 1 – 4;,
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Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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. HPLC of Formula: C7H7N3

Compound 473: 1 -(1 H-benzo[d]imidazol-6-yl)-5-(2,6-difluorophenyl)-3-hydroxy-4- methyl-1 H-pyrrol-2(5H)-one; 1H-Benzoimidazol-5-ylamine (1 mmol) was dissolved in 5ml_ of dry EtOH and 2,6-difluoro – benzaldehyd (1 mmol) were added. The solution was stirred overnight and after that 2-oxal- propionsaure diethylester (1 mmol) was added and the solution was stirred for 2Oh at 500C. After that the solvent was evaporated and remaining oil was subjected to a flash chromatography device and purified by means of a CHC^/MeOH gradient. The purified carboxylic acid ethyl ester derivative was suspended in 1OmL of a 10% aqueous solution of HCI and kept for 3h at reflux. The resulting precipitate was filtered off and dried.Yield: 0.098g (28 %);1H-NMR 400 MHz, CD3OD11.81 (s, 3H, CH3), 6.17(s, 1 H, CH-N), 6.72 – 6.83 (m, 1 H, aro), 6.93 – 7.08 (m, 1 H, aro) 7.21 -7.37 (m, 1 H, aro), 7.74(m, 2H, benzimid), 8.07 (s, 1 H, benzimid), 9.28 (s, 1 H, benzimid) MS m/z 342.0 (M+H)+, HPLC (254 nm): purity 99 % molecular weight (g/mol): 341.31 Ki: hQC (nM): 29.2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 934-22-5, its application will become more common.

Reference:
Patent; PROBIODRUG AG; WO2008/55945; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 139481-72-4, 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. 139481-72-4 name is Trityl candesartan, 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.

Example 15: Deprotection without Acid; A solution of trityl candesartan c (TCS, 350 g, 410.3 mmol), toluene (1050 mL), methanol (2100 mL) and water (17.0 mL) was refluxed for about 2-4 h (HPLC control), the solvents were evaporated at 40-50 C/P<100 mbar to give a residue as a viscous oil, the residue was dissolved at 45-55 C in a mixture of Toluene/Methanol (1041g, 95: 5, w/w) to give a clear solution. The solution was cooled to (-5)- (20) C the solution was kept at this temperature for about 8-12 hr, the precipitated solids were filtered off, washed on the filter with cold Toluene (350 mL) to give a wet solid (295.8 g, 83.0%) 110 g of the wet solid were dried at 50C/10 mbar for 2-6 hr to give a wet white solid (94g (LOD= 15-25%) ). The wet white solid (43.75 g) was dissolved at 40-60 C in Ethanol Absolute (215-363 mL 6- 10V), the solution was filtered and returned to the reactor, then the solution was cooled to (-15)- (5) C and was kept at this temperature for about 2-24 hr. The precipitated solids were filtered off, washed with cold Ethanol Absolute (23-35 mL) to give wet solid which was dried at 50 C/10 mbar to constant weight to give cilexetil candesartan (21.5 g, 67 %). At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trityl candesartan, and friends who are interested can also refer to it. Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/37821; (2005); 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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, A new synthetic method of this compound is introduced below., Quality Control of 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: The mixture of 0.1mol of phenoxy acetic acid derivative(PAA1-PAA5) and 0.1mol of dicyclohexyl carbodiimide in10 mL dichloromethane was stirred at room temperature.After 30 minutes, a solution of AB or APB in 20 ml of dichloromethaneand 5 ml of pyridine was added. The reactionmixture was stirred initially at 0C for 2 h followed by stirring at room temperature for 12 h. The precipitated dicyclohexylureawas removed by filtration and the solvent wasdistilled at reduced pressure on rotary vacuum evaporator.The dried product was dissolved in ethyl acetate (10 mL) andthe solution was washed with 10% aqueous solution of sodiumbicarbonate followed by distilled water to remove thetraces of residual dicyclohexylurea. The ethyl acetate layerwas dried with anhydrous magnesium sulphate and then solventwas distilled off to obtain the crude product which wasrecrystallized from ethanol-water mixture.

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; Singh, Gurmeet; Bansal, Yogita; Bansal, Gulshan; Goel, Rajesh Kumar; Medicinal Chemistry; vol. 10; 4; (2014); p. 418 – 425;,
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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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 51605-32-4

To a mixture of ethyl 4-methyl-1H-imidazole-5-carboxylate (7.30 g, 45.9 mmol) in THF (60 mL) is added MeOH (2.23 mL, 55.1 mmol) and triphenylphosphine (14.8 g, 55.1 mmol). The reaction is cooled to 0° C. under N2 and diethyl azodicarboxylate (9.0 mL, 17.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred overnight. The volatiles are evaporated in vacuo. Ether (50 mL) is added. The mixture is stirred at room temperature for 30 minutes, filtered, the filter cake is washed with ether (50 mL). The filtrate and ether washings are combined and are sequentially washed with water (30 mL) and brine (30 mL). The organic phase is dried over Na2SO4, evaporated in vacuo to provide the crude product. The crude product is subjected to silica gel flash column eluting with 30percent EtOAc in hexanes to EtOAc to give the title compound (5.13 g, 59.8percent) as a yellow oil. LC/MS (m/z): 169 (M+H).

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; Eli Lilly and Company; Hu, Zhi Long; Liu, Lian Zhu; Ma, Tianwei; Zhang, Haizhen; Zhou, Jingye; (25 pag.)US2018/194755; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 45676-04-8,Some common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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: 1-substituted 3-allylimidazolium chloride (2 mmol) was dissolved in 25 mL of dichloromethane and transferred into a Schlenk vessel. Excess Silver(I) oxide (1.5 mmol) was added, and the mixture was stirred for24 h at room temperature under argon atmosphere [19]. Then the unreactedAg2O was filtered through a plug of Celite. The resulting solution was filtered through celite, solvent was evaporated in vaccuo,washed with diethylether (2 mL×2) and dried in vacuo.[RuBr2(PPh3)3] (1 g, 1 mmol) was taken up in 5 mL of dichloromethane and added to a solution of Ag complex in 10 mL of CH2Cl2. The mixture was stirred overnight at room temperature. After filtration in air, the solvent was removed in vacuum to give the product. The final compound is stable in air. Single crystals of the compound 3a were achievedby slow evaporation of a concentrated solution in a mixture of dichloromethane and acetone.

The synthetic route of 45676-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Murugan, Kaliyappan; Vijayapritha, Subbarayan; Viswanathamurthi, Periasamy; Bertani, Roberta; Malecki, Jan Grzegorz; Inorganica Chimica Acta; vol. 486; (2019); p. 55 – 62;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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 137049-00-4, HPLC of Formula: C4H5ClN2O2S

(1-Methylimidazol-4-yl)sulfonyl chloride (23 mg, 0.13 mmol) was added dropwise to a stirred solution of 3-[4-(2-ethyl-5-methyl-2H-pyrazol-3-yl)piperidin-1-yl]-1-phenylpropylamine (see Example 8) (48 mg, 0.15 mmol) and Et3N (20 muL, 0.14 mmol) in CH2Cl2 (2 mL) at RT under N2. The mixture was stirred for 18 h, then was diluted with CH2Cl2 (20 mL) and washed with NaHCO3 solution (20 mL). Then the organic layer was separated and the aqueous phase was re-extracted with CH2Cl2 (20 mL) and the combined organic extracts dried (MgSO4), and concentrated under reduced pressure. The residue was taken up in Et2O (5 mL) and purified by trituration. The title compound (55 mg, 56%) was isolated as a colourless solid. 1H NMR (d6-DMSO, 400 MHz) delta8.28 (1H, d, J=7.8 Hz), 7.68 (1H, s), 7.54 (1H, s), 7.26-7.14 (5H, m), 5.81 (1H, s), 4.35-4.25 (1H, m), 3.93 (2H, q, J=7.2 Hz), 3.60 (3H, s), 2.75-2.50 (3H, m), 2.09 (3H, s), 2.08-2.00 (2H, m), 1.95-1.40 (8H, m), 1.27 (3H, t, J=7.2 Hz). MS (ES+) C24H34N6O2S requires: 470, found: 471 (1:1, M+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, 1-Methyl-1H-imidazole-4-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chambers, Mark Stuart; Jones, Philip; Szekeres, Helen Jane; US2004/2504; (2004); 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. 83741-35-9, name is 4-Bromo-1H-benzoimidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-1H-benzoimidazole

Preparation 46B: 4-Bromo-l- 2,4-difluorophenyl)-lH-benzo[d]imidazole[00149] A vial charged with molecular sieves, 4A (200 mg, 2.030 mmol) was flame- dried, then allowed to cool to room temperature. To this vial were added 4-bromo-lH- benzo[d]imidazole (0.400 g, 2.030 mmol), copper (II) acetate (0.553 g, 3.05 mmol), and 2,4-difluorophenylboronic acid (0.962 g, 6.09 mmol) followed by (¾(¾ (Volume: 10.15 ml) and triethylamine (0.736 ml, 5.28 mmol). The heterogeneous green reaction was stirred at room temperature. After 19 h, the reaction was filtered through a disposable filter funnel and the filter cake rinsed with (¾(¾. The filtrate was concentrated to afford a green residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (12 g column, 30 mL/min, 0-45% EtOAc in hexanes over 15 min, tr = 10.5 min) gave Preparation 46B (7.5 mg, 0.024 mmol, 1.195% yield) as a yellow solid. MS (ESI) : m/z = 31 1.0 [M+H]+. HPLC Peak tr = 1.73 minutes. HPLC conditions: Column:Luna CI 8 4.6x30mm 3u A: 10:90 H20:ACNNH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow.

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 83741-35-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HUANG, Audris; WO2012/44537; (2012); 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. 45676-04-8, name is 1-tert-Butylimidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H12N2

General procedure: Liquid 1-methylimidazole (a) or 1-phenylimidazole (b) or 1-tert-butylimidazole (c) (1 mol equiv.) was added to a stirring solutionof compound 3 (1 mol equiv.) in 50 mL of CH3CN. The reactionmixture was heated at refluxing temperature for 48 h. Then,the reaction mixturewas reduced in vacuo and the resulting oil wasstirred in diethyl ether. The diethyl ether layer was decanted awayto give ligand 4a, 4b and 4c. The spectral data for these compoundsare consistent with those reported in the literature [25,26,29].

The synthetic route of 45676-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Choo, Kar Bee; Lee, Sui Mae; Lee, Wai Leng; Cheow, Yuen Lin; Journal of Organometallic Chemistry; vol. 898; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem