Author: Jessica.F

1848-84-6, name is 2-Ethyl-1H-benzo[d]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. SDS of cas: 1848-84-6

A mixture of 4-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8- yl)piperidine-l -carboxylic acid tert-butyl ester (375 mg, 0.858 mmol), 2-ethylbenzimidazole (151 mg, 1.03 mmol), Xphos (43 mg, 0.09 mmol) and Cs2CO3 (421 mg, 1.29 mmol) in dioxane (5 niL) was degassed with nitrogen bubbling for 15 minutes.Tris(dibenzylideneacetone)dipalladium (20 mg, 0.022 mmol) was added and the mixture was heated to 120 0C for 20 hours. The reaction mixture was diluted with EtOAc, filtered, concentrated in vacuo and purified by column chromatography (Si-PCC, EtOAcxyclohexane, 40-90percent) affording 647 (390 mg, 83percent). LCMS: Rx 4.54 min, [M+H]+ 547.24 1H NMR (400 MHz, DMSO): delta 8.00-7.99 (m; 1 H); 7.68-7.60 (m; 1 H); 7.25-7.24 (m; 2 H); 4.45-4.12 (m; 4 H); 4.12-4.01 (d; J = 13.26 Hz, 2 H); 3.85-3.70 (m; 6 H); 3.25- 3.10 (m, 4 H); 3.04-2.82 (m, 2 H); 2.00-1.90 (d; J = 13.26 Hz, 2 H); 1.76-1.59 (m, 2 H); 1.43 (s; 9 H); 1.35 (t, J = 7.44 Hz, 3 H).

The synthetic route of 1848-84-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
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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 106429-59-8 as follows. Application In Synthesis of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde

A solution of intermediate 2 (100 mg, crude HCI salt, 0.29 mmol) and 2-oxo-2,3-dihydro-1H-benzo[d]jimidazole-5-carbaldehyde (CAS: 106429-59-8) (71 mg, 0.44 mmol) in MeOH (2 mL) was stirred at room temperature for 2 h. NaBH3CN (37 mg, 0.58 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with H2O and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na,SOu, filtered and concentrated. The residue was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19*150 mm 10 um, Mobile Phase A: H20 (0.1% TFA), B: ACN)to give the racemic Compound 14 (49 mg, TFA salt). The obtained racemic Compound 14 was separated by SFC (SFC80, Waters, IC 2.5*25 cm, 10 um, A: Supercritical COQ., B: MeOH/DEA= 100/0.03; A:B = 70/30; Flow rate: 70 mL/min; column temperature (T): 25 C; Backpressure (BPR): 100 bar) to give Compound 108 (12 mg as TFA salt, 6.8% yield) as a white solid and Compound 109 (13 mg as TFA salt, 7.3% yield) as a white solid.

According to the analysis of related databases, 106429-59-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
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Electric Literature of 1402838-08-7,Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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 10b (210 mg, 1.180 mmol) , 2-hydroxyisoindoline-1, 3-dione (38 mg, 0.233 mmol) , Bis (acetylacetonato) cobalt (30 mg, 0.117 mmol) in HOAc (5 mL) was stirred under oxygen atmosphere at 75 for 6 h. The reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with EtOAc (10 mL) and the insoluble solid was filtered off. The filtrate was concentrated in vacuo to afford a crude mixture of 14b and 14c (160 mg) as slight brown oil, which was used for the next step without further purification. To a stirred mixture of compound 10a (150 mg, 0.362 mmol) and compounds 14b and 14c (70 mg, 0.362 mmol) in anhydrous THF (10mL) was added dropwise a solution of EtONa (21in EtOH, 152mg, 0.471mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. After the mixture was concentrated to dryness under reduced pressure, the residue was diluted with NH4Cl solution (10mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was dissolved in MeOH (8 mL) . To this solution was added HOAc (2 mL) , and the reaction mixture was stirred at 60 for 2 h. The mixture was concentrated in vacuo to give a residue, which was diluted with NaHCO3saturated solution (10 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (EtOAc) to afford compound 14d (70 mg, 55yield) , MS 349.2 [M+H]+, and 14e (40 mg, 31yield) as a light yellow solid, MS Found 365.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1-Trityl-4-imidazolyl)benzaldehyde, its application will become more common.

Reference:
Patent; HANGZHOU INNOGATE PHARMA CO., LTD.; ZHANG, Hancheng; LIU, Shifeng; (53 pag.)WO2016/165613; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, Recommanded Product: 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole

A mixture of 1a (0.70 g , 2.0 mmol), bis(pinacolate)diborane (0.53 g, 2.1 mmol), l,l’-bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Cl2) (0.060g,0.08mmol), andanhydrous potassium acetate (0.393 g, 4.0 mmol) in 1,4-dioxane(20 mL) was heated at 80C under nitrogen for 12 h. After cooling to room temperature, the mixture was extracted with ethyl acetate (30 mL*3). The organic extracts were washed with water, brine, and then dried with anhydrous MgSO4. After filtration, the filtrate was pumped dry in vacuo. The crude residue was subjected to column chromatography by eluting with hexanes/EA (8:1) as the eluent to give a white solid (yield: 81%). 1H NMR (400 MHz, acetone-d6): d (ppm ) 7.79 (d, J 7.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 2H), 7.62-7.56 (m,5H), 7.45 (d, J=7.6 Hz, 2H), 7.37-7.23 (m, 3H) and 1.34 (s, 12H); 13C NMR (125 MHz, acetone-d6): d (ppm) 152.9, 144.3, 138.6, 138.2, 135.2, 134.0, 131.0, 129.7, 129.6, 128.6, 124.3, 123.7, 120.7, 111.4, 84.9, 25.3; Mass (FAB ): m/z: 397.1 [M+H]+.

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Reference:
Article; Muangpaisal, Rossatorn; Hung, Wei-I.; Lin, Jiann T.; Ting, San-Yu; Chen, Li-Yin; Tetrahedron; vol. 70; 18; (2014); p. 2992 – 2998;,
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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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H3BrN2

43. 5-(4-Bromo-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one A stirred mixture containing 11.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 16.6 g of 4-bromo-1H-imidazole and 100 ml of N-methylpyrrolidinone was heated in an oil bath at 135-140 C. for 22 hours. The reaction mixture was cooled and diluted with 200 ml of water. The resulting precipitate was collected, washed with water, air-dried, combined with 1.5 g of 5-(4-bromo-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one prepared in another run starting with 1 58 g of 5-bromo-1,6-naphthyridin-2(1H)-one, recrystallized twice from dimethylformamide and dried in an Abderhalden drying pistol at 90 for 22 hours, after which the sample still contained 0.2 mol of dimethylformamide per mol of product. The material was then dissolved in 100 ml of 5% aqueous sodium hydroxide solution, the solution filtered and the filtrate solidified with acetic acid.

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; Sterling Drug Inc.; US4657915; (1987); A;,
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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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Safety of Methyl 1H-imidazole-5-carboxylate

[0174] A solution of compound 12 (18.0 g, 142.7 mmol, 1.0 eq) and hydrazine hydrate (35.7 g, 713.7 mmol, 5.0 eq) in EtOH (200 mL) was stirred at 90 C for 15 h. After cooling to room temperature, a precipitate formed. The solid was filtered, and dried under vacuum to afford compound 13 (15.0 g, 119 mmol, 83% yield) as a white crystalline solid: 1H NMR (400 MHz, DMSO-d6) 6 4.35 (br. s., 2H) 7.61 (s, 1H) 7.72 (d, J=0.88 Hz, 1H) 9.10 (br. s., 1H) 12.49 (br. s., 1H).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENITH EPIGENETICS CORP.; BROWN, Samuel, David; COBURN, Craig, Alan; KHARENKO, Olesya; (103 pag.)WO2016/92375; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, 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 96797-15-8, Quality Control of 4-Iodo-1-trityl-1H-imidazole

Ethyl magnesium bromide (IM) in tetrahydrofuran (12.66 mL, 12.66 mmol) was added to the solution of 4-iodo-l-trityl-lH-imidazole (4.6g, 10.55 mmol) in freshly distilled dry tetrahydrofuran (46.0 mL) at an ambient temperature and the reaction mixture was stirred for about 90 minutes. Zinc chloride (IM) (12.66 mL, 12.66 mmol) was added at an ambient temperature and was stirred for another about 90 minutes. The reaction mixture was degassed for about 20 minutes. Tetrakis(triphenylphosphine) palladium (0.61g, 0.527 mmol) and 5-bromo-2-chloro pyrimidine (2.24 g,l 1.6 mmol) was added and the reaction mixture was stirred for about 12-14 hours at about 700C. The reaction mixture was cooled and diluted with dichloromethane, washed with aqueous solution of EDTA (PH=9), brine, dried over anhydrous sodium sulphate, filtered and concentrated to form the solid, which was purified by column chromatography using ethyl acetate-hexane as eluents. Yield: 3.0g

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Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2007/60618; (2007); A2;,
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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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

To a suspension of 4-bromo-3-chloro-5-(trifiuoromethyl)aniline (15 g, 54.7 mmol, APAC) in CH2C12 (200 ml) was added 1 ,1 ‘-thiocarbonyldiimidazole(l 1.7 g, 65.6 mmol) at 0 C. The reaction was stirred cold for 30 minutes and then at RT overnight. The reaction mixture was concentrated and the crude material was purified by flash chromatography (silica gel, 220g, 5% to 15%) DCM/Hexanes) to give a yellow oil as desired product (12.3g, 71% yield).

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); A1;,
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Related Products of 670-83-7,Some common heterocyclic compound, 670-83-7, name is 2,5-Diphenyl-1H-imidazole, molecular formula is C15H12N2, 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 3 2,5-diphenyl-4-hydroxymethyl-imidazole hydrochloride 5 g (0.0227 mole) of 2,4-diphenyl-imidazole, 0.85 g (0.0283 mole) of paraformaldehyde and 0.1 g of finely ground potassium hydroxide are dissolved in 29 ml of warm methanol and heated under reflux for 90 hours. The solution is then decolourized with activated carbon, filtered and dried. Water and chloroform are added to the residue by stirring; the insoluble solid of both the layers is filtered, washed with water and chloroform and dried. 2.8 g (yield 49.3%) of crude product is thus obtained, which is crystallized from methanol to afford 1.1 g of 2,5-diphenyl-4-hydroxymethyl-imidazole, m.p. 206-207 C. (dec.) By the usual techniques the hydrochloride has been obtained, m.p. about 220 C. (dec.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Diphenyl-1H-imidazole, its application will become more common.

Reference:
Patent; Zambon S.p.A.; US4560696; (1985); A;,
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Some common heterocyclic compound, 30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, molecular formula is C7H10N2O2, 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: 30148-21-1

General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2×100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 30148-21-1, its application will become more common.

Reference:
Article; Venkat Ragavan; Vijayakumar; Rajesh; Palakshi Reddy; Karthikeyan; Suchetha Kumari; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4193 – 4197;,
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