Month: June 2021

73746-45-9, name is 5-Iodo-2-methyl-1H-imidazole, 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. Application In Synthesis of 5-Iodo-2-methyl-1H-imidazole

4-IODO-2-METHYL-LH-IMIDAZOLE (200 mg, 1.0 mmol), 4-fluorophenylboronic acid (215 mg, 1.6 mmol), copper (II) acetate (210 mg, 1.2 mmol) and ET3N (0.16 ml, 1.2 mmol) were sus- pended in 10 ml THF and oxygen was bubbled through the reaction mixture for 40 min. The reaction mixture was stirred for 48 hours at RT and then filtrated over DICALIT. The filtrate was concentrated and then purified by flash chromatography to yield 1- (4-FLUORO- PHENYL)-4-IODO-2-METHYL-LH-IMIDAZOLE (120 mg, 0.40 mmol, 41 %).

The synthetic route of 73746-45-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/80998; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 1003-21-0 as follows. Product Details of 1003-21-0

intermediate 15: step b(1-methyl-1H-imidazol-5-yl)(pyrimidin-2-yl)methanone5-Bromo-l -methyl- IH-imidazole (6.66 g, 41.4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N? atmosphere. The contents were cooled to 0 C in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0CC and a solution of iV”niethoxy~A,;-methylpyriniidine-2~carboxa.mide (3,09 g, 15.9 mmol, Intermediate 15: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C, then slowly warmed to room temperature, then heated to 40 C in an oil bath and heated with stirring at that temperature for approximately 36 hours. The contents were then cooled to 0 C, quenched with a saturated aqueous NH4C1 solution, diluted with ethyl acetate and transferred to a separatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgS04, filtered, then distilled under reduced pressure to afford an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM / (10% of a 2 M N3 MeOH in DCM)) to provide the title compound.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; 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.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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. Application In Synthesis of 1-Methyl-1H-imidazole-4-carboxylic acid

To a solution of (+/-) -cis-N1- (2-chloro-6- (furan-2-yl) pyrimidin-4-yl) cyclohexane -1, 3-diamine (150 mg, 0.51 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) were added N, N-diisopropylethylamine (0.26 mL, 1.54 mmol) and 1-methyl-1H-imidazole-4-carboxylic acid (129 mg, 1.03 mmol) . The mixture was stirred at rt for 10 minitues, and then HATU (389 mg, 1.03 mmol) was added. The resulting mixture was stirred at rt for 3 h. The reaction mixture was diluted with water (20 mL) , and the resulting mixture was extracted with EtOAc (20 mL× 3) . The combined organic layers were washed with saturated brine (50 mL) , dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (150 mg, 73percent) .[0587]MS (ESI, pos. ion) m/z: 401.2 [M+H]+.

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (0 pag.)WO2018/157830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 124750-92-1, 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 124750-92-1 as follows.

460 grams of free acid was dissolved in 5 liters of acetic acid, glacial. The solution was filtered through a glass frit. The filtrate was added to 6 liters of 1.1 N HCl in acetic acid, glacial over 1 hour. Crystallization began just prior to the end of filtrate addition, and the resulting material was aged for 1 hour. An ice and water bath was added to cool the batch, and the batch was aged 1 hour. 12.5 liters of isopropyl acetate was added over 1 hour, and the resulting material was aged at 3-4C for 1 hour.Resulting material was filtered and washed with 1 liter isopropyl acetate displacement wash, 2 x 1 liter isopropyl acetate slurry wash, and 2.5 liter isopropyl acetate displacement wash. Resulting material was air dried 45 minutes, then dried by pulling nitrogen through filter cake overnight followed by drying at 350C in a vacuum oven until constant weight. The resulting hydrochloric acid salt was 2-butyl~4-chloro- l-[(2′-(l-H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxylic acid hydrochloride Form I. The solid was then analyzed by X-ray Powder Diffraction. The diffractogram for 2-butyl-4-chloro-l-[(2′-(l- H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxylic acid hydrochloride Form I is characterized by principal d-spacings of 12.96, 4.75, 3.97, 3.79, 3.77, 3.71, and 3.44A, more specifically 12.96, 8.32, 8.13, 7.06, 5.18, 4.75, 4.64, 4.45, 4.41, 4.33, 4.19, 3.97, 3.86, 3.79, 3.77, 3.71, 3.59, 3.44, 3.15, and 2.92A.

According to the analysis of related databases, 124750-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/115834; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3012-80-4, 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 3012-80-4 as follows.

To a mixture of thiazolidinedione (6a, 0.5mmol), 1-methyl-1H-benzo[d]imidazole-2-carbaldehydes (10a, 0.55mmol) in ethanol (4mL) was added catalytic amount of piperidine. The reaction mixture was refluxed until complete conversion as observed by TLC. After cooling, the precipitates were filtered, washed and recrystalized with ethanol, to obtain pure (Z)-5-((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)thiazolidine-2,4-dione derivative 11a as yellow solids. All the other compounds 11b?t were obtained in a similar reaction procedure of 11a in moderate to high yields. 5.1.1 (Z)-5-((1-Methyl-1H-benzo[d]imidazol-2-yl)methylene)-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)thiazolidine-2,4-dione (11a) Yellow solid, Yield 82percent; mp: 264?266°C; FT-IR: (cm?1): 2985, 2964, 1740, 1679, 1659, 1385, 1220, 750; 1H NMR (500MHz, DMSO-d6): delta 7.99 (s, 1H), 7.78 (d, J=8.1Hz, 1H), 7.69 (d, J=8.1Hz, 1H), 7.39 (t, J=7.9Hz, 1H), 7.32 (t, J=7.5Hz, 1H), 4.50 (s, 2H), 4.02 (s, 3H), 3.55 (t, J=6.6Hz, 2H), 3.31 (t, J=7.3Hz, 2H), 1.97?1.89 (m, 2H), 1.84?1.77 (m, 2H); 13C NMR (125MHz, DMSO-d6): delta 169.6, 164.8, 162.6, 147.3, 142.6, 135.8, 128.1, 124.2, 123.1, 119.6, 116.7, 111.0, 45.7, 45.0, 42.7, 29.8, 25.8, 23.6; HRMS (ESI): m/z calcd for [M+H]+ C18H19N4O3S 371.1178; found 371.1171.

According to the analysis of related databases, 3012-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sharma, Pankaj; Srinivasa Reddy; Thummuri, Dinesh; Senwar, Kishna Ram; Praveen Kumar, Niggula; Naidu; Bhargava, Suresh K.; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 608 – 621;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-56-4, 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. 16681-56-4, name is 2-Bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

20 g (0.136 mmol) of 2-bromo-lH-imidazole and 3.9 g (0.163 mmol) of sodium hydride were dissolved in 500 ml of THF in a round-bottomed flask, and the solution was stirred and refluxed under a nitrogen stream for one hour. Then, 40.5 g (0.217 mmol) of 3-(2-bromoethyl)pyridine was added thereto in a dropwise fashion, and the mixture was stirred and refluxed for 3 hours. When the reaction was complete, sodium hydride remaining therein was quenched by methanol. After separating an organic layer and an aqueous layer, a solvent therein was all removed. Subsequently, a resultant therefrom was treated through column chromatography, obtaining 23 g of an intermediate compound-15 (a yield: 67%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEIL INDUSTRIES INC.; KIM, HYUN JUNG; CHAE, MI YOUNG; LEE, NAM HEON; HUH, DAL HO; KIM, WOOK; KIM, YOUN HWAN; KIM, JUN SEOK; LEE, SANG IL; LEE, HYUN GYU; JANG, CHUN KEUN; JUNG, JU YEON; (32 pag.)KR2015/66887; (2015); A;,
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

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

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