Imidazoles-derivatives

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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 16681-56-4

To a microwave vial was added 6-(2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-5 dioxaborolan-2-yl)phenyi)-N-methyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine(Intermediate 9-3, 100 mg, 0.21 mmol), 2-bromo-1 H-imidazole (61.2 mg, 0.42 mmol), Na2C03 (44mg, 0.42 mmol), and Pd(PPh3)2CI2 (14 mg, 0.02 mmol), followed by DME (1 mL)/EtOH 0.25ml)/(H20 (0.25 ml). The vial was purged with N2 for 10 min and the reaction mixture was heated at150C in a microwave reactor for 20 min. The reaction mixture was filtered through celite and the10 filter cake was washed with EtOAc. The filtrate was concentrated in vacuo to give the crude productwhich was purified by silica gel chromatography (5%-15% MeOH/DCM) to afford 6-(4-(1 H-imidazol-2-yl)-2-methoxyphenyi)-N-methyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (40 mg,MS: 421.3 [M+H+]).

The synthetic route of 16681-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEUNG, Atwood; CHIN, Donovan Noel; DALES, Natalie; FAZAL, Aleem; HURLEY, Timothy Brian; KERRIGAN, John; O’BRIEN, Gary; SHU, Lei; SUN, Robert; SUNG, Moo; WO2014/28459; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 670-96-2, name is 2-Phenyl-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. Computed Properties of C9H8N2

Into a 15mL pressure tube, sequentially add 1a (43.3mg, 0.3mmol), dichloromethane (3mL), 2h (68.5mg, 0.45mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3bb (58.3 mg, 66%) as a white solid.

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

Reference:
Patent; Henan Normal University; Zhang Xinying; Zhang Linghua; Xu Yuanshuang; Fan Xuesen; (23 pag.)CN110372708; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57531-37-0, 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 57531-37-0 as follows.

Example 4246To a stirred solution of compound 45 (0.7 mmol) in dry DMF is added K2CO3 (1.4 mmol) and NaI (0.066 mmol)and stirred for 30 min at rt. Then compound 2-chloro-4nitro-imidazol (0.84 mmol) is added at rt and stirred for over night at 80 0C and the reaction is monitored by TLC. The reaction mixture is diluted with water and extracted with DCM (3 x 25 mL) and washed with water, brine and dried (over with Na2SO4) and concentrated under vacuum. The crude compound is purified over neutral alumina using 30percent EtOAc/pet-ether as eluent to give 46. MS: M+ 396.3

According to the analysis of related databases, 57531-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; US DEPARTMENT OF HEALTH & HUMAN SERVICES; WO2007/75872; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 152628-02-9, 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of I (30.4 g, 0.10 mol), the title compound 4′-chloromethylbiphenyl-2-carbonitrile (0.12 mol) of Example 14, Sodium ethoxide (or other organic bases as described above) (0.3 mol) Mixed with DMF (or other solvents as previously described) (200 ml) and reacted at 65 C for about 5 hours. After TLC was tested for no material, ethylene glycol (100 ml and water (50 ml) (Or other aqueous solvent) and heated to 160 C. TLC detection of no raw materials, the ice water to adjust the concentration of concentrated hydrochloric acid to 5 to 6, The solid was precipitated and the resulting solid was filtered, washed with water, telmisartan crude product, by recrystallization of telmisartan.

The synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Specialization Pharmaceutical Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Wu Mingjun; Li Jianfeng; Chen Weiming; Tian Guanghui; Zhu Fuqiang; Suo Jin; Shen Jingshan; (14 pag.)CN104768936; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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 20485-43-2, Formula: C5H6N2O2

A solution of the dipyrrole (50 mg, 0.138 mmol) resulting after coupling of the pyrrolicacid 10, as described in the previous experiment, in MeOH:DMF (4.5 mL : 0.7 mL) was hydrogenated for 1 h over 10% palladium on charcoal (30 mg). The catalyst was removed by filtration through celite and the filtrate concentrated. The residue was dissolved in DMF (1.0 mL), cooled to 0 C and added to a solution of acid 12 (13.4 mg,0.106 mmol), DECP (0.04 mL, 0.212 mmol), Et3N (0.13 mL, 0.903 mmol) and DMAP(catalytic) in THF (3.0 mL) at -10 C. The mixture was stirred for 15 h at -10 C. Thesolvents were removed under reduced pressure and the resulting residue purified by flash chromatography (aluminum oxide, 10% MeOH) to give 1b as a yellow-brownsolid (30.7 mg, 66%).

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:
Article; Jimenez-Balsa, Adrian; Dodero, Veronica I.; Mascarenas, Jose L.; Tetrahedron; vol. 69; 36; (2013); p. 7847 – 7853;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

4-iodo-1H-imidazole (20 g, 103 mmoles) was dissolved in DMF (100 mL) then triethylamine (15.1 mL, 108 mmoles) and triphenylmethyl chloride (27.8 g, 100 mmoles). The reaction mixture was stirred at room temperature for 48 h, then poured into ice water (500 mL), and then evaporated to dryness, and filtered, and dried to give white crystals of 4-iodo-1-triphenylmethyl-1H-imidazole (40 g, 91.7 mmol, 88.9%).

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; Shenzhen Weixin Biological Technology Co., Ltd.; Yu Jindi; Lu Xianping; Li Zhibin; Xin Lijun; Zhu Jiangfei; Fu Chao; (67 pag.)CN108203438; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-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. name: 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole

A suspension of 6-bromo-4-fluoro-2-methyl-1-(propan-2-yl)-1H-benzimidazole (Int-46) (90 g, 331.95 mmol), bis(pinacolato)diboron (126 g, 498 mmol), AcOK (80 g, 815.15 mmol), tricyclohexylphosphine (14 g, 49.8 mmol), and Pd(OAc)2 (7.45 g, 33.2 mmol) in DMSO (1.0 L) was sparged with N2 and then stirred at 100 C. for 16 h. TLC analysis (1:1 petroleum ether/EtOAc) showed complete consumption of the starting material. The black suspension was poured into H2O (3.0 L) and extracted with EtOAc (2*3 L). The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (Biotage, 1.0 kg, 0-40% EtOAc/petroleum ether) to provide 4-fluoro-2-methyl-1-(propan-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole (A-1) (77 g, 73% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.69 (s, 1H), 7.33 (d, J=10.8 Hz, 1H), 4.77-4.61 (m, 1H), 2.65 (s, 3H), 1.65 (d, J=7.0 Hz, 6H), 1.36 (s, 12H); m/z (ESI+) for (C17H24BFN2O2), 319.2 (M+H)+.

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Chen, Ping; Cho-Schultz, Sujin; Deal, Judith Gail; Gallego, Gary Michael; Jalaie, Mehran; Kania, Robert Steven; Nair, Sajiv Krishnan; Ninkovic, Sacha; Orr, Suvi Tuula Marjukka; Palmer, Cynthia Louise; (169 pag.)US2019/330196; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, 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 23814-14-4, Safety of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid

To a stirred solution of 2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carboxylic acid (70 mg), l-(piperazin-l-yl)ethanone84 (50.4 mg) and N,N-diisopropylethylamine (206 mu) in DMF (1 ml) was added HATU (224 mg). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated in vacuo and the residue was purified by preparative reverse-phase HPLC (Gemini NX CI 8, 12 nm, 5mu, 100 x 30 mm, flow rate 40 ml/min, eluant: CH3CN/H2O containing formic acid) followed by lyophilisation to afford 5-(4-acetylpiperazine- l-carbonyl)-lH-benzo[d]imidazol-2(3H)-one (50 mg, 44%) as white solid. MS (ISP): 289.1 ([M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); 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. 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H11N3O

3-Methoxy-4-(4-methyl-lH-imidazol-l-yl)benzonitrile (3.50 g, 16.4 mmol) was suspended in tetrahydrofuran (31.6 ml) in a nitrogen gas atmosphere at -10C and then, to the resultant suspension were added dropwise a Vitride (TM, manufactured by Sigma- Aldrich Corporation) toluene solution (65 wt%, 3.47 g, 11.2 mmol) using a syringe. After completion of the dropwise addition, the solution was stirred at -10C for one hour, and disappearance of the raw material was confirmed by TLC (silica gel; developing solvent: ethyl acetate; UV detector). Acetone (0.26 mL, 3.58 mmol) was added to the reaction mixture and stirred for 10 minutes, and then the resultant mixture was added dropwise to 5 M hydrochloric acid (18 mL) cooled at 7C while stirring, followed by temperature elevation to room temperature. The resultant solution was added dropwise to a mixture of a 5 M aqueous sodium hydroxide solution (20.4 mL) and toluene (32 mL), which was cooled to 7C in advance, while stirring, and the temperature of the resultant mixture was elevated to room temperature. The lower layer (aqueous layer) was separated from the organic layer, the aqueous layer was further extracted with toluene (18 mL) and the toluene layer and the above organic layer were combined. The combined organic layer was washed with a 10% aqueous sodium chloride solution (18 mL x 4) and then filtered through a Celite (1 g) pad, and the resultant filtrate was concentrated under a reduced pressure at a water bath temperature of 50C. The residue was further subjected to azeotropic distillation with toluene under a reduced pressure to obtain 3.70 g of a crude product containing a title compound.The obtained crude product was dissolved in a mixture of toluene (3.5 mL) and acetone (7 mL) at 60C, and n-heptane (15.8 mL) was slowly added dropwise to the resultant solution while stirring so that the internal temperature was maintained at 50C or higher. After completion of the dropwise addition, the solution was subjected to crystallization (seed crystal: lotNo. A6103102) at 53C, the water bath was removed and the slurry was gradually cooled to room temperature and stirred overnight. The resultant slurry was further cooled to 7C and stirred for 9 hours and 30 minutes, and then the solids were collected by filtration and washed with an acetone/n-heptane (1/3) mixture which was cooled to 7C in advance, and dried under a reduced pressure at 45 to 50C for 1.5 hours to obtain 2.64 g of a title compound (yield: 74.4%). The quantitative determination by HPLC showed that the loss of the compound into the mother liquor was 0.435 g (12.3%).The above-obtained title compound (2.64 g) and the mother liquor (containing 0.435 g of the compound) were mixed together, the mixture was concentrated, the concentrate was dissolved in a mixture of toluene (3 mL), acetone (6 mL), and tert-butyl methyl ether (18 mL), which was warmed at 48C, and then the resultant solution was cooled to 42C to perform a crystallization. The resultant slurry was gradually cooled to room temperature and stirred overnight. To the slurry was further added dropwise tert-butyl methyl ether (9 mL), and then the resultant mixture was stirred for one hour, cooled to 8C and stirred for one hour, followed by stirring at 4C overnight (17 hours). The solids were collected by filtration and dried under a reduced pressure to obtain 1.97 g of a title compound (yield: 64.6%). The quantitative determination by HPLC showed that the loss of the compound into the mother liquor was 0.674 g (22%).

According to the analysis of related databases, 1243204-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai R&D Management CO., LTD.; YOSHIKAWA, Seiji; KAYANO, Akio; WO2011/37244; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5805-57-2, A common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, molecular formula is C8H9N3, 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: NH4SCN (0.092 g, 1.2 mmol) was dissolved in water (5 ml) and slowly added to the methanolic solution of CuCl2¡¤2H2O (0.1 g; 0.59 mmol) and suitable N-donor ligand, and stirred at room temperature for 12 h. Green crystalline precipitates were filtered off and dried in air. The crystals suitable for X-ray structure determination were obtained by slow recrystallization from methanol.

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:
Article; Machura; ?witlicka; Mrozi?ski; Kali?ska; Kruszynski; Polyhedron; vol. 52; (2013); p. 1276 – 1286;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem