Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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 39021-62-0, Product Details of 39021-62-0

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (3.0 g, 6.97 mmol, Intermediate 10: step d) was added THF (40 ml) and the solution was cooled to -70 C. n-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1-methyl-1H-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C. bath. After 35 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5*50 mL. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (30% acetone-DCM increasing to 5% MeOH) provided the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 8.21 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.60 (dd, J=8.6, 1.9 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 7.33 (s, 1H), 6.65 (s, 1H), 6.04 (s, 1H), 4.34 (s, 2H), 4.07 (s, 3H), 3.55 (s, 3H). MS (ESI): mass calcd. for C23H19ClF3N3O2, 461.1, m/z found 462.1 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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.; US2015/105372; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 14741-71-0,Some common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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 P: Preparation of 1H-benzo[d]imidazole-2-acethydrazide 15 g 1H-benzo[d]imidazole-2-acetic acid ethyl ester (0.074mol), 100 mL anhydrous ethyl alcohol and 37 mL of 80% hydrazine hydrate were added to a three-necked bottle and reacted under reflux for 4 hours. A white solid was isolated. After sucking filtration, the filter cake was washed with ethanol. After drying, 10.7 g white solid was obtained. Yield: 76%, MS: 191(M+1).

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

Reference:
Patent; Shenyang J & Health Pharmaceutical Co., Ltd.; EP2468730; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 14741-71-0,Some common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

Add 2-ester benzimidazole (0.5 mmol) and 5-chloro-2-bromobenzaldehyde (0.6 mmol) to the dry Schlenk tube, evacuate nitrogen, and add piperidine (0.05 mmol), 1, 4-Dioxane (2 ml), and the reaction was stirred at room temperature for 3 hours. At room temperature, CuI (0.05 mmol) K2CO3 (1 mmol) and 1,10-phenanthroline (0.1 mmol) were added to the reaction system, and then the mixture was heated to 90 C. and stirred for 8 hours. After stopping the reaction, 15 ml of CH2Cl2 was added to the reaction system, filtered through a sand funnel, and washed with CH2Cl2 three times. The filtrate and washing solution were combined, dried over anhydrous Na2SO4, and concentrated and separated by silica gel column chromatography (eluent: ethyl acetate). Ester: dichloromethane = 30: 1) to obtain the pure product. The material was a yellow solid with a yield of 37%.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Zhou Bingwei; Lu Lulu; Bao Hanyang; (18 pag.)CN110872288; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1450-93-7, 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1) belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 5-methylfuran-2-carbaldehyde (200 mg, 2 equiv.), 2- aminoimidazole hemisulfate (240.1 mg, 1 equiv.) and TEA (281 pL, 2.2 equiv.) in dichloromethane (6 mL) was added Ti(/PrO)4 (619.5 mg, 2.4 equiv.) and the mixture was stirred at room temperature for 16 hours. Volatiles were evaporated. The concentrated mixture was dissolved in MeOH (6 mL) and NaBH4 (172 mg, 5 equiv.) was added portionwise every 30 minutes until almost complete conversion to the wanted amine. The reaction mixture was transferred to a separatory funnel containing NaHCCf (15 mL), and extracted with DCM (2x 15 mL). The combined organic extracts were dried over Na2S04, were filtered, and the solvent was removed in vacuo to yield the crude product (222 mg). LCMS: MW (calcd): 177.20; MS (ES+, m/z)·. 178.08 [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, 1H-imidazol-2-amine sulfate(2:1), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E-THERAPEUTICS PLC; POLJAK, Tanja; MODRIC, Marina; VADLAMUDI, Srinivasamurthy; STUBBERFIELD, Colin; (0 pag.)WO2019/229464; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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. Quality Control of 5-Bromo-1-methyl-1H-imidazole

To a flask containing 5-bromo-1-methyl-1H-imidazole (360 mg, 2.24 mmol) was added THF and the solution was cooled to 0 C. To this clear homogeneous solution was added isopropyl magnesium chloride-LiCl complex (1.3 M, 2.3 mL, 2.98 mmol) which resulted in a white suspension. The reaction mixture was stirred at 0 C. for 30 min, and a THF (2 mL) solution of N-methoxy-N,2,6-trimethylnicotinamide (522 mg, 2.69 mmol, Intermediate 40, step a) was introduced and the mixture was allowed to warm to room temperature for 3 hours and then heated to 50 C. for 20 hours. The contents were cooled to room temperature, poured into a saturated NH4Cl solution and extracted with EtOAc (4×50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography on silica gel (25-50% Acetonitrile-DCM increasing gradient to 5% MeOH-DCM) afforded the title compound as a pale yellowish solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-21-0, its application will become more common.

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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
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 60-56-0 as follows. Quality Control of 1-Methyl-1H-imidazole-2(3H)-thione

Dithiafulvalenyl compound 1 (0.2 mmol), mercapto-thiazole 2 (2 mmol, 10 equiv.), and I2 (0.6 mmol, 3 equiv., 152.4 mg) were dissolved in DMSO (3 mL). The reaction mixture was stirred at 25 C for 12 h under N2 atomsphere. Then quenched with a saturated solution of Na2S2O3 and stirred for half an hour, the solution was extracted with dichloromethane (CH2Cl2). The organic layer was separated, and dried over Na2SO4. Then the organic solvent was removed in vacuo to afford the respective thiadiazole-based dithiafulvalene (DTF) derivatives (3), which were purified by column chromatography (silica gel, PE / CH2Cl2) to afford pure substances.

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fu, Huimin; Zhao, Bangtun; Zhu, Weimin; Tetrahedron Letters; vol. 60; 2; (2019); p. 124 – 128;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1,3-cyclohexanedione (561 mg, 5.0 mmol) and imidazole (340 mg, 5.0 mmol) in CH2C12 (50 ml) was added neat N-trifluoroacetyl imidazole (2.27 ml, 20 mmol). The reaction mixture was stirred at room temperature for 45min. The reaction was diluted with 4N aq. HCl and the layers were separated. The aqueous layer was extracted 2x CH2C12. The combined organics were washed with H20 and brine. The organics were dried over MgS04, filtered and concentrated. The crude product was used directly for the next step.

The chemical industry reduces the impact on the environment during synthesis 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven S.; CANNIZZARO, Carina E.; CHOU, Chien-hung; HALCOMB, Randall L.; HU, Yunfeng Eric; LINK, John O.; LIU, Qi; SCHROEDER, Scott D.; TSE, Winston C.; ZHANG, Jennifer R.; WO2013/6738; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1467-16-9, A common heterocyclic compound, 1467-16-9, name is 1H-Imidazole hydrochloride, molecular formula is C3H5ClN2, 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.

Solutions of [H(imidazolium)][Cl] (0.048 g, 45 mmol) in 2 mL CH3CN and K2B12F12 (0.10 mg, 0.22 mmol) in 2 mL CH3CN were mixed at room temperature, affording 0.10 g of salt 3 (93% yield). Single-crystal X-ray diffraction analysis confirmed the composition of this salt.

The synthetic route of 1467-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Belletire, John L.; Schneider, Stefan; Shackelford, Scott A.; Peryshkov, Dmitry V.; Strauss, Steven H.; Journal of Fluorine Chemistry; vol. 132; 11; (2011); p. 925 – 936;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]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 405173-97-9, SDS of cas: 405173-97-9

The crude isoquinuclidine hydroiodide (106 mg, 0.40 mmol) , obtained by TMSI deprotection of 8 and triethylamine (0.17 mL, 121 mg, 1.2 mmol) in anhydrous DMF (1.5 mL) was stirred under argon at room temperature for 10 min. 2-(2′- chloroethyl ) benzimidazole (72 mg, 0.40 mmol) was then added to the above mixture and the resulting solution was allowed to stir at room temperature overnight. After the workup, the crude mixture was purified by RP-HPLC to afford a pale yellow oil (48 mg, 43% yield) . 1R NMR (300 MHz, CD3OD) delta 7.68 (2H, dd, J= 6.2, 3.2 Hz), 7.48 (2H, dd, J= 6.2, 3.1 Hz), 6.75 (1H, dd, J= 7.7, 7.7 Hz), 6.25 (1H, dd, J= 7.7, 7.7 Hz), 4.25 (1H, d, J= 5.2 Hz), 3.60 (3H, m) , 3.45 (2H, m) , 2.93 (1H, m) , 2.80 (1H, d, J= 10.5 Hz), 2.14 (1H, m) , 1.94 (1H, ddd, J= 12.6, 9.1, 2.9 Hz), 1.25 (1H, m) , 1.04 (1H, m) , 0.94 (1H, dddd, J= 7.9, 5.2, 2.6, 2.6 Hz), 0.85 (3H, t, J= 7.4 Hz); 13C NMR (75 MHz, CD3OD) delta 150.5, 140.4, 133.5, 133.5, 127.1, 127.1, 126.0, 115.1, 115.1, 59.9, 53.6, 53.3, 37.1, 30.8, 29.1, 28.9, 23.5, 11.3; m/z calcd for C18H23N3 281.19, found 281.73.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; SAMES, Dalibor; LI, Xiaoguang; LI, Shu; KRUEGEL, Andrew; KARPOWICZ, Richard; CARRERA, Ignacio; RAKSHIT, Souvik; WO2013/28999; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4, These common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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.

To a solution of 3-((2-hydroxy-3-nitrobenzyl)(methyl)amino)-N,N-dimethylpropanamide (KR-400450) (3.70 mmol, 1.04 g) in methanol (125 mL), PtO2 (0.18 mmol, 0.04 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring.The reaction was then stirred under hydrogen atmosphere at ordinary pressure (15 psi) for three hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (90 mL). The filtrate was concentrated in vacuo yielding a brown oil. The oil was quickly re-dissolved in acetonitrile (175 mL) and di(imidazole-1-yl)methanimine (7.39 mmol, 1.19 g)was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (10:1 chloroform/methanol) provided a faint orange oil in a 64% yield. The product ofthe reduction (3-((3-amino-2-hydroxybenzyl)(methyl)amino)-N,N-dimethylpropanamide) is air sensitive and appropriate measures should be taken to minimize air exposure. An analytical sample of the title compound was isolated by reverse-phase HPLC utilizing a gradient from 3.0-20% acetonitrile in water.

Statistics shows that Di(1H-imidazol-1-yl)methanimine is playing an increasingly important role. we look forward to future research findings about 104619-51-4.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem