Month: June 2021

Synthetic Route of 19225-92-4, 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 19225-92-4 as follows.

[0242] A solution of tert-butyl 5-(2-(3-hydroxyphenyl)quiiiazolin-4-ylammo)-lH- indazole-1-carboxylate (50mg, 0.11 mmol), 2-(chloromethyl)-l -methyl- lH-imidazole (22 EPO mg, 0.13 mmol), KI ( 22 mg, 0.13 mmol), K2CO3 (76 mg, 0.55 mmol) in anhydrous DMF (1.2 mL) was heated at 500C for 100 minutes. Added 1.2 equivalents each of 2- (chloromethyl)-l-methyl-lH-imidazole and KI and heated for another 35 minutes. Added 2.4 equivalents each of 2-(chloromethyl)-l-methyl-lH-imidazole and KI along with 2.0 equivalents OfK2CO3 and heated for 1 h. The solution was diluted with CH2Cl2 and washed with aqueous saturated NaCl (2x). The organic phase was dried under Na2SO4 and concentrated in vacuo to afford tert-butyl 5-(2-(3-((l-methyl-lH-imidazol-2-yl)methoxy)- phenyl)quinazolin-4-ylamino)-lH-indazole-l-carboxylate.

According to the analysis of related databases, 19225-92-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SURFACE LOGIX, INC.; BARTOLOZZI, Alessandra; SWEETNAM, Paul; WO2006/105081; (2006); A2;,
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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 53710-78-4

General procedure: 60% NaH (9.6mg, 0.24mmol) was added to a solution of 5a (100mg, 0.24mmol) in dry DMF (10mL) at room temperature. After stirring for 30min, 1-(3-chloropropyl)-1H-imidazole (52mg, 0.36mmol) was added and the mixture was then stirred for 5h at 80C. After cooling, the mixture was poured into cold water (200mL) and extracted with EtOAc (3×50mL). The combined organic phase was washed with brine (3×150mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using dichloromethane/ 20 methanol/triethylamine (120:4:1, v/v/v) as eluent to afford 64.4mg (51.0%) 6a as a red solid.

The synthetic route of 53710-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Xiaoqi; Hu, Yuanyuan; Gao, Anhui; Xu, Meng; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Li, Jia; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 589 – 603;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

Ethylmagnesium bromide (3 M in Et2O, 1.04 mL, 3.11 mmol) was added dropwise to a solution of 5-bromo-1-methyl-1H-imidazole (500 mg, 3.11 mmol) in DCM (6 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature 15 min, then was cooled in an ice bath prior to addition of N-methoxy-N-methylpyridazine-4-carboxamide (419 mg, 2.51 mmol, Intermediate 29, step a). The resulting suspension was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl, diluted with water, and extracted three times with EtOAc. The aqueous phase was saturated with NaCl and back-extracted with DCM (three times). The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, gradient 30-100% CH3CN-DCM, followed by isocratic 5% MeOH-acetone), affording title compound contaminated with 1-methyl-1H-imidazole, the mixture of which was used in the next reaction without further purification.

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; 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

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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: The mixture of 0.1mol of phenoxy acetic acid derivative(PAA1-PAA5) and 0.1mol of dicyclohexyl carbodiimide in10 mL dichloromethane was stirred at room temperature.After 30 minutes, a solution of AB or APB in 20 ml of dichloromethaneand 5 ml of pyridine was added. The reactionmixture was stirred initially at 0C for 2 h followed by stirring at room temperature for 12 h. The precipitated dicyclohexylureawas removed by filtration and the solvent wasdistilled at reduced pressure on rotary vacuum evaporator.The dried product was dissolved in ethyl acetate (10 mL) andthe solution was washed with 10% aqueous solution of sodiumbicarbonate followed by distilled water to remove thetraces of residual dicyclohexylurea. The ethyl acetate layerwas dried with anhydrous magnesium sulphate and then solventwas distilled off to obtain the crude product which wasrecrystallized from ethanol-water mixture.

According to the analysis of related databases, 2963-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Singh, Gurmeet; Bansal, Yogita; Bansal, Gulshan; Goel, Rajesh Kumar; Medicinal Chemistry; vol. 10; 4; (2014); p. 418 – 425;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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 1H-imidazol-2-amine sulfate(2:1)

2-Aminoimidazole sulfate (11.6 g) is dissolved in 7.4 mL of concentrated HCl, 8 mL of water, and 40 mL of acetic acid. The resulting solution is cooled to 0 C. To the solution is added a solution of 6.08 g of NaNO2 in 16 mL of water dropwise where the internal temperature is maintained under 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1,4-diethyl-1,2,3,4-tetrahydroquinoxaline, 13.1 g of sodium acetate and 40 mL of acetic acid is cooled to 0 C. To this slurry is added the diazonium solution slowly and the internal temperature of the reaction is maintained below 5 C. After the addition is complete, the resulting violet suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a large beaker containing 400 g ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is extracted with dichloromethane 6 times to yield crude (E)-6-((1H-imidazol-2-yl)diazenyl)-1,4-diethyl-1,2,3,4-tetrahydroquinoxaline (19.5 g, impure). This material is used in the next step without further purification.

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 760212-58-6

Under a nitrogen atmosphere, 5.0 g (14.3 mmol) intermediate compound M5, 4.0 g (15.8 mmol) of bis- dioxaborolane, 4.2 g (42.8 mmol) of potassium acetate, and 0.58 g (0.71 mmol) of [1,1′- bis (diphenylphosphino) ferrocene ] palladium ( II ) dichloride dichloromethane adduct were added to 100 mL of N,N- dimethylformamide in a 300-mL three-neck flask and were heated to 80C and then stirred at the same temperature for 4 hours. [0177 ] The mixture was cooled to room temperature and 100 mL of water added thereto. The mixture was stirred for 1 hour and was then filtered. The resulting solid residue was slurry-washed with water to give crude crystals of intermediate compound M6. [ 0178 ] The resulting crude crystals were dissolved in toluene. The solution was purified by column chromatography (toluene/ethyl acetate = 4/1), followed by recrystallization from a solvent mixture of toluene/heptane = 4:1. The resulting crystals were dried under reduced pressure to give 4.12 g (yield: 72.7%) of intermediate compound M6.

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; CANON KABUSHIKI KAISHA; TAGAMI, Kei; OHRUI, Hiroki; IWAWAKI, Hironobu; ITABASHI, Masumi; TAKAHASHI, Tetsuo; IKARI, Kenichi; ISHII, Ryuji; MURATSUBAKI, Masanori; WO2014/24687; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. Recommanded Product: 60-56-0

Triethylamine (0.0749 g, 0.75 mmol) was added to a solution of2-mercapto-1-methylimidazole (0.0856 g, 0.75 mmol) in tetrahydrofuran(15 mL) and the mixture was stirred for 30 min at roomtemperature. Then, 1-(bromomethyl)pyrene (0.1476 g, 0.5 mmol)was slowly added and the reaction mixture was heated underreflux for 24 h. After cooling to room temperature, the mixture wasfiltered and the solvent was evaporated, the crude residue waspurified by column chromatography (1:1 ethyl acetate/petroleumether) to obtain a brown solid of compound 2 (0.1301 g, 79.3%yield). Characterization of compound 2: 1H NMR600 MHzd6-DMSO3.62 (s, 3H), 3.87 (d, 2H), 7.12 (s, 1H), 7.45 (s, 1H), 7.63(dd, 2H), 8.15 (m, 1H), 8.28 (d, 1H), 8.32 (m, 2H), 8.36 (m, 2H), 8.38(d, 1H), 8.50 (d, lH). Mass spectra (Fig. S2): calculated for C21H16N2S[M+H]+, 329.1; found, 328.81.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Jing; Jiang, Huihui; Liu, Hai-Bo; Liang, Lebao; Tao, Junrong; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 228; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, 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 17289-25-7, HPLC of Formula: C5H8N2O

General procedure: Freshly prepared Ag2O (2.20 mmol) was added at room temperature to a solution of pyridin-2-ylmethanol (1.00 mmol) and 2-iodopropane (2.20 mmol) in 1,4-dioxane (10 mL) and stirred for 24 h. The reaction mixture was filtered through a Celite bed and washed with ethyl acetate. Filtrate was concentrated under vacuum.The resulting material was purified by flash chromatography on a Biotage instrumentusing 4-g flash cartridge and eluted with 12?15percent ethyl acetate in hexane to give isopropyl picolinate (2) (65percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1-Methyl-1H-imidazol-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Patil, Vikas S.; Reddy, M. Rajendar; Pal, Shyam Sundar; Sharma, Somesh; Reddy, L. Krishnakanth; Synthetic Communications; vol. 44; 14; (2014); p. 2121 – 2127;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2, HPLC of Formula: C3H3BrN2

(i) Production of (1H-Imidazol-4-yl)-(naphthalen-2-yl)ketone 4-Bromo-1H-imidazole (1.95 g) was dissolved in THF (30 ml), and the solution was cooled to -78 C. To the solution was added a solution of t-butyllithium in pentane (1.7 M; 20 ml). The mixture was stirred at 0 C. for 1.5 h. The mixture was again cooled to -78 C., and a solution of 2-formylnaphthalene (3.32 g) in THF (20 ml) was added. After the temperature was elevated from -78 C. to room temperature, the mixture was stirred at room temperature for 16 h. To the mixture was added an aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography,(eluent, dichloromethane_methanol=10:1). Recrystallization from dichloromethane-methanol gave the titled compound (1.00 g) as a colorless solid. 1H-NMR (CDCl3) delta: 7.53-7.70 (2H, m), 7.84-8.40 (6H, m), 8.53 (1H, s), 10.82 (1H, brs). IR (KBr): 2592, 1640, 1127, 779 cm-1.

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; Takeda Chemical Industries, Ltd.; US6573289; (2003); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1072-62-4, These common heterocyclic compound, 1072-62-4, name is 2-Ethyl-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.

40 mmol of 2-ethylimidazole was dissolved in 20 ml of dimethylsulfoxide (DMS0), and the mixture was milledNa0H80mmol, heated to 60 C, then add 40mmol chloromethyl benzotriazole, 60 C water bath heating lh, cooling to room temperature,Poured into 100g ice water, stirring, precipitation, filtration, precipitation washed 3 times with water to get crude;The crude product was recrystallized from ethyl acetate to give the colored crystals as the ligand 1- (benzotriazole-1-methyl) -1- (2-ethylimidazole).

Statistics shows that 2-Ethyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1072-62-4.

Reference:
Patent; Henan College of Traditional Chinese Medicine; Wang, Xia; Zhang, Chao; Ceng, Dai; Cheng, Di; Song, Ning; Yang, Huai Xia; (11 pag.)(2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem