Month: April 2021

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. 18672-03-2, name is 5,6-Dichloro-1H-benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows., name: 5,6-Dichloro-1H-benzo[d]imidazol-2-amine

2-Amino-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole (43) 2-Amino-5,6-dichlorobenzimidazole (4) (3 g, 16 mmole) was dissolved in dry acetonitrile (150 ml) and stirred in an inert atmosphere at 60 C. BSA (4.37 ml, 17 mmole) was added and the mixture was stirred for 10 minutes. 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (5.09 g, 16 mmole) and TMSTf (3.29 ml, 17 mmole) were added to the clear solution and the mixture was allowed to stir at 60 C. for 1 hr. The mixture was concentrated under reduced pressure and separated on a silica column to yield 1.14 g (15%) of 2-amino-5,6-dichloro-1-(2,3,5,tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole (43). 13 C NMR (CDCl3): d 170.04 ppm, 169.56, 169.11, 154.57, 141.64, 132.53, 125.90, 1123.45, 117.72, 109.49, 85.78, 80.99, 70.95, 69.83, 62.91, 20.74, 20.54, 20.20. 1 H NMR (CDCl3): d 0.96 ppm (s, 3H), 1.09 (s, 3H), 1.13 (s, 3H), 3.75 (m, 2H), 4.08 (dd, 1H), 5.00 (dd, 1H), 5.13 (t, 1H), 5.42 (s, 2H), 5.61 (d, 1H), 7.27 (s, 1H), 7.42 (s, 1H). MS (FAB): m/e 758, 718, 676, 460, 426, 259, 217, 139.

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 18672-03-2.

Reference:
Patent; The Regents of the University of Michigan; US5574058; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2302-25-2, These common heterocyclic compound, 2302-25-2, name is 4-Bromo-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.

General procedure: A reaction vessel A’-1 (1.74g, 17.0mmol), A’-2 (2.07g, 17.0mmol), Tetrakis(triphenylphosphine)palladium (0.7g, 1.08mmol), Potassium carbonate (5.3 g, 38.3mmol), toluene (60 mL), ethanol (20 mL) and distilled water (20 mL) were added, followed by stirring at 60 C for 3 hours.After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, dried over MgSO 4, and then the organic solvent was removed, and A-1 (1.67 g, 68%) was obtained by silica column method

The synthetic route of 2302-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Choi Don-su; Choi Jin-sol; (70 pag.)KR2019/35043; (2019); A;,
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. 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 20485-43-2

To a stirred solution of 2- [5-(azetidin-3-ylamino)-pyridin-3-yl] -5-chloro-3,3-dimethyl-2,3- dihydro-isoindol-1-one (Example lEA], 56 mg, 0.163 mmol) and Et3N (0.5 mL) in DCM (5 mL) was added HATU (124 mg, 0.326 mmol) and 1-methylimidazole-2-carboxylic acid(27 mg, 0.2 12 mmol) at room temperature and stirring was continued at room temperature for 1 hour. The resulting reaction mixture was extracted with EtOAc (2 x 50 mL) and the combined organics were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by Prep-HPLC to afford title compound (15.4 mg, 21%) as a white foam. MS: 451.1 (M+Hj.

According to the analysis of related databases, 20485-43-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191340; (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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 32673-41-9

Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.

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 32673-41-9.

Reference:
Patent; Merck & Co., Inc.; US5780488; (1998); A;; ; Patent; Merck & Co., Inc.; US6063930; (2000); A;; ; Patent; Merck & Co., Inc.; US5919785; (1999); A;; ; Patent; Merck & Co., Inc.; US5925651; (1999); 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C8H6N2O2

To a stirred solution of compound 189 (24 g, 148 mmol) in DCM (250 mL) under inert atmosphere, DIPEA (51.58 mL, 296 mmol) and HATU (84.39g, 222 mmol) were added. To this solution, N,O-dimethylhydroxylamine hydrochloride (21.66 g, 222 mmol) was added and stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and extracted using DCM. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 50% EtOAc/ hexanes to afford compound 190 (15 g, 49.40%) as a white solid. TLC: 5% MeOH/ DCM (Rf: 0.5); 1H NMR (400 MHz, DMSO-d6): delta 13.19 (s, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.54 (d, J=7.6 Hz, 1H), 7.34- 7.24 (m, 2H), 3.83 (s, 6H); LCMS Calculated for C10H11N3O2: 205.09; Observed: 206 (M+1)+.

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; ASSEMBLY BIOSCIENCES, INC.; TURNER, William, W., Jr.; LI, Leping; HAYDAR, Simon, Nicolas; BURES, Mark, G.; RAI, Roopa; FRANCIS, Samson; ARNOLD, Lee, Daniel; (0 pag.)WO2018/160878; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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 28890-99-5, Safety of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

Example 16 3.3 g (6.9 mmol) of bromo compound, 2.1 g (10 mmol) of 6H-benzimidazolo[1 ,2- a]benzimidazole, 0.39 g (2.1 mmol) of copper(l) iodide, 14 g (123 mmol) of trans-1 ,2- cyclohexanediamine and 4.8 g (23 mmol) of tri potassium phosphate in 30 ml of 1 ,4-dioxane are reflux for 24 h. The reaction mixture is cooled at room temperature and added 200 ml of 1 N aqueous hydrochloric acid. The inorganic solids are filtered, then the filtrate is extracted with dichloromethane. The organic layer is dried over sodium sulfate and concentrated in vacuo. Gradient column chromatography on silica gel with dichloromethane/ethyl acetate (dichloromethane100%, 95/5, 1/1 ) gives the product. Yield 2.4 g (58 %). 1H NMR (400 MHz, CDC ): delta 8.18 – 8.10 (m, 2H); 8.04 – 7.96 (m, 2H); 7.94 – 7.87 (m, 2H); 7.87 – 7.79 (m, 4H); 7.78 – 7.73 (m, 1 H); 7.71 – 7.59 (m, 5H); 7.43 – 7.32 (m, 7H); 7.31 – 7.27 (m, 1 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, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SAITO, Masatoshi; NAGASHIMA, Hideaki; (118 pag.)WO2017/178864; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 152628-02-9 name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

32.24 g of 2-n-propyl-4-methyl-6-(1′-methylbenzimidazol-2′-yl)benzimidazole x H2O is placed in 100 mL of dimethylacetamide (DMA), and 11.8 g of potassium tert-butoxide is added batchwise with stirring at approximately 20 C. and then the mixture is stirred for one hour at about 20 C. The mixture is cooled to 5 C. and then a mixture of 28.6 g of 4-bromomethyl-2′-cyanobiphenyl and 95 mL of DMA (dissolved at approximately 20 C.) is added dropwise over about 30 minutes. The temperature of the reaction mixture is maintained at approximately 5 C.-10 C. by cooling with the ice bath. Then it is rinsed with 5 mL of DMA and stirred for a further 1.5 hours at 5 C. to 10 C. [0045] The solvent is largely distilled off under a water-jet vacuum, during which time the product crystallizes out. The residue is cooled to 60 C., diluted with 230 mL of tert-butylmethylether and stirred for 1 hour without any energy input, then cooled to 15 C. to 20 C. and stirred for another hour at this temperature. The crystals are suction filtered, washed batchwise with 100 mL of tert-butylmethylether, then with 250 mL of water, and then dried in a vacuum drying cupboard at 80 C. Yield: 43.3 g (87.5% of theory); melting point: 196 C.-197 C.; HPLC: >99.9%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2004/236113; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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. Product Details of 28890-99-5

d) Intermediate (E-3) (1.3 g, 7.0 mmol) and benzoimidazolo[1,2-a]benzimidazole (1.52 g, 7.3 mmol) were entered in N-methylpyrrolidone (20 mL). To the mixture was potassiumphosphate (3.12 g, 14.7 mmol) added, and the mixture was stirred at 180C for 40 h. After the reaction mixture was cooled at room temperature, 50 mL of water was poured into the reaction mixture to give a grey solid. The solid was collected by filtration, and washed with water and ethanol. The crude product was purified by column chromatography on silica gel eluting with CH2CI2 to yield 1.87 g (71%) of compound (B-i) as a white solid.1HNMR (300 MHz, CDCI3): 6 7.98-7.95 (m, 2H), 7.81-7.73 (m, 4H), 7.63 (dt, J = 0.8,8.3Hz, 1H), 7.45-7.35 (m, 4H), 730-7.26 (m, 1H), 7.12 (dt, J= 0.8, 8.0 Hz, 1H), 7.04 (td, J=0.9, 7.6 Hz, 1 H), 6.91 (dq, J = 0.6, 1.5, 7.9 Hz, 1 H)

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; NISHIMAE, Yuichi; KOHLSTEDT, Julia; SCHAeFER, Thomas; NAGASHIMA, Hideaki; (114 pag.)WO2016/97983; (2016); 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 41716-18-1

Synthesis of { 2- ( 6-chloropyridin-3-yl ) -4- ( 2- methoxyethoxy ) -7, 8-dihydropyrido [4, 3-d] pyrimidin-6 (5H) – yl) ( l-neio-lif-imidazol-4-yl ) }methanone (compound no. 6) is shown in scheme 4. l-Tert-butyl-3-ethyl-4-oxopiperidine-l, 3- dicarboxylate (12) underwent a facile three-component condensation with 6-chloropyridine-3-carboximidamide hydrochloride (13) and 2-bromoethyl methyl ether followed by Boc- deprotection to afford advanced an intermediate 14, which was coupled with l-methyl-l.fi-imidazole-4-carboxylic acid (15) (Scheme 4) . See, Raheem, et al., Bioorg. Med. Chem. Lett. 22:5903-5908 (2012) .

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 41716-18-1.

Reference:
Patent; UNIVERSITY OF SOUTH ALABAMA; PIAZZA, Gary, A.; WO2015/6689; (2015); 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. 71759-89-2, name is 5-Iodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C3H3IN2

To a solution of 3 (3.5 g,18.0 mmol) in DMF (70 mL) was added TEA (3.0 mL, 21.7 mmol) andtrityl chloride (5.5 g, 19.7 mmol). After stirring at 20 C for 24 h, thesolution was poured into water. The solid was filtered to yield thecrude compound that was purified by flash column chromatographyon silica gel to afford 4 as a white solid (7.4 g, 94.0%). Mp148e150 C. 1H NMR (300 MHz, Chloroform-d) d(ppm) 6.9 (m, 1H),7.0e7.2 (m, 6H), 7.25e7.4 (m, 10H). MS (EI) m/z 437.1 [MH].

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem