Author: Jessica.F

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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1H-Imidazole

lH-imidazole (65-1, 10 g) was dissolved in 150 mL of THF with dimethylsulfamoyl chloride (19 g), followed by the drop-wise addition of TEA (20 g). The mixture was stirred at rt for 16 h, then poured into 200 mL of water and extracted with EtOAc. The organic layer was dried with Na2S04. Solvent was removed to give compound 65-2 as a light yellow oil.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; GALEMMO, Robert, A., Jr.; ARTIS, Dean, Richard; YE, Xiaocong, Michael; AUBELE, Danielle, L.; TRUONG, Anh, P.; BOWERS, Simeon; HOM, Roy, K.; ZHU, Yong-Liang; NEITZ, R., Jeffrey; SEALY, Jennifer; ADLER, Marc; BEROZA, Paul; ANDERSON, John, P.; WO2011/79114; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 120781-02-4, These common heterocyclic compound, 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, 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.

(1) 2-bromo-3-methyl -3H- to imidazole-4-carboxylic acid methyl ester (800mg) 4-(trifluoromethyl)benzeneboronic acid(1.04g), tetrakis(triphenylphosphine)palladium(422mg) And as a solvent was stirred in tetrahydrofuran (9), saturated sodium carbonate (3), was added water (1.5), and microwave irradiation for 30 minutes at 120 . After the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (n- hexane: ethyl acetate) [(trifluoromethyl) 4-phenyl] After purification, 3-methyl-2–3H- imidazole-4-carboxylic acid methyl ester ( It was obtained 980mg) as a yellow solid.

Statistics shows that Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 120781-02-4.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-38-6,Some common heterocyclic compound, 3034-38-6, name is 5-Nitro-1H-imidazole, molecular formula is C3H3N3O2, 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.

Step A: To a mixture of 4-nitro-lH-imidazole (1.5 g, 13.27 mmol) and TEA (2 mL, 14.59 mmol) in DMF (12 mL) at 0 C was added trityl chloride (3.7 g, 13.27 mmol). The mixture was allowed to warm to rt and was stirred for 1 h. The mixture was poured onto ice and 1 N aq NaOH (2 mL) was added. The solid was collected by filtration washing with water to afford 4-nitro-l -trityl- lH-imidazole as a solid (4.58 g, 96%).

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBIT BOISCIENCES CORPORATION; HADD, Michael, J.; WO2012/30914; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic 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. Computed Properties of C5H6N2O2

Examples; CRYSTAL FORMS OF ZOLEDRONIC ACID (ZLD-Ac); Preparation of ZLD-AC crystal form I; General procedure for the preparation of ZLD-AC crystal form I starting from 1- Imidazoleacetic acid (IAA), Phosphorous acid (H3PO3) and Phosphorous oxychloride (POC13) (Examples 1-9, see Table 1) :; A cylindrical reactor equipped with a mechanical stirrer, a thermometer, a reflux condenser and a dropping funnel, is loaded with 1-IMIDAZOLEACETIC acid (IAA), Phosphorous acid and a diluent (Toluene/Chlorobenzene/PEG-400/Silicon oil). The obtained suspension is heated to 75C-80C and Phosphorous oxychloride is added drop- wise. The reaction mixture is then heated to 75C-100C for 1-34 hours. Then water is added at 80C-100C. The mixture is stirred vigorously for about 15 minutes. [In some cases, when Silicon oil is used as a diluent, there is a need to add Toluene in order to improve the separation between the oily phase and the aqueous phase]. Then the phases are separated. The aqueous phase is put in a clean reactor and heated to 95C-100C for 13.5-19 hours. Then it is cooled to 5C and absolute Ethanol is added to obtain a precipitate after stirring at 5C for 2.5-4 hours [In some cases a precipitate of Zoledronic acid is obtained without adding absolute Ethanol as an anti-solvent]. The white product is then filtered, washed with absolute Ethanol and dried in a vacuum oven at 50C for 17-24 hours to obtain Zoledronic acid crystal form I (LOD BY TGA=6. 3%-9. 3%).; ZLD HPLC METHOD: COLUMN: PHENOMENEX PHENYL-HEXYL 5UM, 250X4.6MM MOBILE PHASE: 40MM OCTANSULFONIC ACID SODIUM SALT IN 1% HCLO4, 0.2% H3PO4 : METHANOL (85:15) DETECTION: 220NM STABILITY WAS MEASURED VERSUS THE PRESENCE OF FORM II. P THE STABILITY DATA FOR EXAMPLE 4 IN THE TABLE ABOVE IS:

The synthetic route of 22884-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/5447; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 118469-15-1, The chemical industry reduces the impact on the environment during synthesis 118469-15-1, name is 5-Fluoro-2-methyl-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

In a 150 mL round bottom flask, intermediate VI-13 2-methyl 5-fluorobenzimidazole (0.31 g, 2.04 mmol) was added, and potassium carbonate was used as a base (0.30 g, 2.20 mmol), and acetonitrile was stirred at 50 C as a solvent. After 40 minutes, after cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C. After concentration, extraction, column chromatography separation, drying, etc., the intermediate X-13 (0.48 g) is obtained in a yield of 77.8%; white solid

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-Fluoro-2-methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei·lamohan·laao·yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

4-Nitrophenol (162 mg, 1.17 mmol) is dissolved in methylene chloride (2 mL). To the solution is added (3-methyl-2-nitro-3H-imidazol-4-yl)-methanol (115 mg, 0.732 mmol) and triphenylphosphine (211 mg, 0.805 mmol). The mixture is stirred at room temperature until a solution is achieved. The solution is then cooled in an ice bath and treated with diisopropyl azodicarboxylate, DIAD (158 uL, 0.805 mmol). After 1 hour the ice bath is removed and the mixture is stirred overnight at room temperature. Crude product is purified on a silica gel column to isolate the product mixed with triphenylphosphine oxide. The solids are triturated with t-butyl methyl ether to remove the triphenylphosphine oxide to afford l-methyl-2-mtro-5- (4-nitro-phenoxymethyl)-lH-imidazole. MS (ESI+) for C11H10N4O5 m/z 279.1 (M+H)+.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39021-62-0, These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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.

Example 7: (3-(4-1H-Pyrazol-1-yl)benzyl)-2,4-dichloroquinolin-6-yl)(1-methyl-1H-imidzol-5-yl)methanolA solution of n-BuLi (2.5 M in hexanes, 0.4 mL, 1 mmol) was added dropwise by syringe to a solution of 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline (0.500 g, 1.15 mmol, Intermediate 4: step c) in dry THF (13.5 mL) in a dry ice-acetone bath. After 1-2 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (141.6 mg, 1.286 mmol) in dry THF (0.2 mL) was added dropwise. The reaction was stirred for 5 minutes and moved to an ice bath for 1.5 hours before allowing the reaction to warm to room temperature. The reaction was quenched with saturated aqueous ammonium chloride. The mixture was partitioned between water and dichloromethane. The separated aqueous phase was further extracted with dichloromethane. The combined organic phase was dried (Na2SO4), filtered, and concentrated. Crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM), followed by reverse-phase chromatography (acetonitriIe H2O + 0.05% TFA). Product fractions were basified with saturated aqueous sodium bicarbonate and extracted with DCM, before being dried (Na2SO4), filtered, and concentrated to provide the title compound. 1H NMR (400 MHz, CD3OD) delta ppm 8.43 (s, 1H), 8.12 (d, J = 2.4 Hz, 1H), 7.96 (dd, J = 8.7, 3.8 Hz, 1H), 7.83 (dd, J = 8.7, 1.6 Hz, 1H), 7.66 (dd, J = 9.6, 2.2 Hz, 1H), 7.62 (d, J = 8.8 Hz, 3H), 7.30 (dd, J = 12.9, 6.5 Hz, 2H), 6.56 (s, 1H), 6.48 (t, J = 2.1 Hz, 1H), 6.14 (s, I H), 4.57 (d. J = 6.1 Hz, 2H), 3.69 (s, 3H); MS m/e 464.1 [M+H]+

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

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.; WO2015/57206; (2015); 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Imidazole-4,5-dicarboxylic acid

In H2O (12ml) solvent, was added CuCl (0.841g, 0.85mmol), 2,2′-bipyridine (0.086g, 0.5mmol), 4,5-imidazole acid (0.078g, 0.5mmol), NaOH (0.020 g, 0.5mmol), placed on a magnetic stirrer was stirred for 30 minutes, the reaction was placed in 25ml teflon-lined autoclave, sealed in a high temperature oven, constant-temperature 160 C for five days to 5 C / h rate down to room temperature, a blue precipitate in the reactor bulk crystal, in 60% yield (based on copper).

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; Capital Normal University; Lu, Xiaoming; Cheng, Yifeng; (14 pag.)CN103965224; (2016); B;,
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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

First, 4-imidazole formaldehyde (1a, 960 mg, 10 mmol) was added to the reaction flask.Place in an ice water bath. After 10 min, triethylamine (TEA) (278 mul, 2.0 mmol) was added to the reaction flask, and the mixture was stirred in the ice water bath for 5 min.Di-tert-butyl dicarbonate (2.4 g, 1.0 mmol) was then added to the reaction flask, and the reaction was moved to room temperature to react overnight.After the reaction was detected to be complete by TLC, the solvent was spin-dried and alumina column chromatography (PE: EA = 2: 1) was used to obtain intermediate 1b.

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 3034-50-2.

Reference:
Patent; Xihua University; Yang Lingling; Wang Zhouyu; Qian Shan; Li Ling; Xu Wei; Yang Huan; Liu Siyan; Yao Hao; Yan Jie; Li Chao; (21 pag.)CN110294713; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-42-2,Some common heterocyclic compound, 3034-42-2, name is 1-Methyl-5-nitroimidazole, molecular formula is C4H5N3O2, 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 solution of compound 1(2.9 g, 22.83 mmol) in THF (35 mL) was added LiHMDS (1.0 M THF solution, 24 mL, 24 mmol) at -40 C under argon. The mixture was stirred at -40 C for 15 minutes.The aldehyde was added slowly with inner temperature kept below -30 C. The mixture was stirred at – 40 C for 75 minutes before quenched with aqueous saturated NH4C1 solution (10 mL).The reaction mixture was extracted with EtOAc (40 mL x 3), washed with brine (50 mL), dried over Na2504.The solvents were removed under reduced pressure and the residue was purified via flash column to afford clear oil (1.5 g, yield 33%).1HNJIVIR (CDC13, 400 IVIHz) : 7.97 ( s, 1H), 4.22 (m, 1H), 4.00 (s, 3H), 2.24-2.14 (m, 1H), 1.06 (d, J = 6.4 Hz, 3H), 0.93 (dd, J = 1.2, 6.4 Hz, 3H)

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-5-nitroimidazole, its application will become more common.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; MATTEUCCI, Mark; CAI, Xiaohong; CAO, Yeyu; JIAO, Hailong; MA, Jing Yuan; DUAN, Jian-Xin; (52 pag.)WO2016/210175; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem