Month: August 2021

Reference of 760212-58-6, A common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, molecular formula is C19H13BrN2, 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.

Synthesis Example 17: Synthesis of Compound A86 (0377) Pd(dba)3 (0.03 eq), (t-Bu)3P (0.06 eq), and toluene (based on a reagent (0.1 M 1 eq)) were added to a flask containing Int D-4 (1 eq) and R?-4 (1.2 eq) to form a mixed solution, and then, the mixed solution was stirred under reflux for 5 hours. After the reaction solution was cooled to room temperature, an extraction process was performed thereon using MC, followed by a washing process performed thereon using distilled water. Then, the resulting product obtained from the washing process was subjected to a drying process using MgSO4 and a vacuum distillation process. The residue obtained therefrom was purified by column chromatography, thereby completing the preparation of Compound A86 (yield: 75%). (0378) HRMS for C40H29N3[M]+: calculated: 551.69, found: 550. (0379) Elemental Analysis for C40H29N3 calculated: C, 87.08; H, 5.30; N, 7.62

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; Samsung Display Co., Ltd.; Lee, Jungsub; (107 pag.)US2017/271596; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3543-72-4,Some common heterocyclic compound, 3543-72-4, name is Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, molecular formula is C14H17N3O4, 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.

[0075] 163 g (559.5 mmol) of compound (5) were dissolved in 1875 g ethanol. 14 g of palladium catalyst on activatedcarbon doped with iron (5% Pd, 1% Fe) and an additional 0.8 g of iron(II) sulfate 7-hydrate or 0.8 g of iron(III) nitrate 9-hydrate were added. Compound (5) was then hydrogenated at a hydrogen pressure of up to 4 bar until completeconversion of the starting compound (5).[0076] The catalyst was removed by filtration, and the ethanolic solution concentrated until a dry product remained.This residue was crystallized from propan-2-ol or ethyl acetate.[0077] The yield of compound (6) was 128 g (489,8 mmol) with a content of > 99 % (87.5 % of theory).[0078] The overall yield of compound (6) was 80.4% of theory in relation to 2-fluoro-5-nitroaniline. In comparison, thesynthesis according to DD34727 starting from N-1-methyl-4-nitrobenzene-1,2-diamine (CAS 41939-61-1) is characterizedby a yield of 39.0%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, its application will become more common.

Reference:
Patent; HEYL Chemisch-Pharmazeutische Fabrik GmbH und Co. KG; Frey, Michael; Walther, Dirk-Detlef; EP2690096; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, molecular formula is C8H6N2O2, 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: 46006-36-4

Step 1: (lH-Benzo[d]imidazol-4-yl)(l-methyl-lH-spiro[chromeno[4,3- c] pyrazole-4,4 ‘-piperidine] -1 ‘-yl)methanone To a solution of l-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (211 mg, 0.830 mmol), lH-benzimidazole-4-carboxylic acid (134 mg, 0.830 mmol) and triethylamine (346 mu?, 2.50 mmol) in dichloromethane (2 mL) was added HATU (314 mg, 0.830 mmol) in one portion and the mixture was stirred for 12 hours. The reaction mixture was treated with 1M NaOH (1 mL) for 10 minutes. Dichloromethane (5 mL) was added. The two layers were separated and the aqueous layer was extracted with dichloromethane (2 5 mL). The organic layers were combined, washed with brine, dried over MgS04, filtered and evaporated to yield a residue that was purified on silica using a gradient of 0.5-30% MeOH in dichloromethane to yield (1 H-benzo[d]imidazol-4-yl)(l -methyl- 1 H-spiro[chromeno[4,3-c]pyrazole-4,4’- piperidine]- -yl)methanone. ESI-MS m/z calc. 399.5, found 400.5 (M+l)+. Retention time: 1.12 minutes (4 min run).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 46006-36-4, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara, Sabina; GROOTENHUIS, Peter, Diederik, Jan; MILLER, Mark, Thomas; ANDERSON, Corey; PONTILLO, Joseph; KALLEL, Edward, Adam; NUMA, Mehdi, Michael, Djamel; FRIEMAN, Bryan, A.; McCARTNEY, Jason; WORLEY, Jennings, Franklin; ARUMUGAM, Vijayalaksmi; UY, Johnny; HILGRAF, Nicole; BEAR, Brian, Richard; WO2013/67248; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-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: 36947-68-9

EXAMPLE 11 2-Isopropyl-1-(6-methylergolin-8beta-ylmethyl)imidazole 0.9 g of 50% sodium hydride in an oil was added to a mixture of 4.0 g of 2-isopropylimidazole and 40 ml of dimethylformamide, and the mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8beta-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 2 hours. The solvent was distilled off under reduced pressure, and water was added to the residue. The precipitated crystals were filtered, washed with water and purified by silica gel column chromatography (eluted with acetone). The crystals thus obtained were dissolved in methanol, and isopropyl alcohol was added thereto. The mixture was concentrated and allowed to cool to obtain 0.6 g of the titled compound as colorless needles having a melting point of 283-288 C. (with decomposition). NMR (CDCl3) delta: 1.18 (1H, q, J=11.7 Hz), 1.34 (3H, d, J=6.7 Hz), 1.35 (3H, d, J=6.7 Hz), 1.80-3.09 (7H, m), 2.43 (3H, s), 3.37 (1H, dd, J=14.3, 4.4 Hz), 3.80 (2H, d, J=6.8 Hz), 6.65-7.25 (6H, m). Elementary Analysis for C22 H28 N4: Calc’d: C. 75.82; H, 8.10; N, 16.03. Found: C, 76.15; H, 8.39; N, 16.25.

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

Reference:
Patent; Maruko Seiyaku Co., Ltd.; US4713457; (1987); A;,
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. 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