Category: imidazoles-derivatives

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

To a solution of 1-methyl-1Himidazole-4-carboxylic acid (0.50 g, 4.0 mmol), 1-hydroxybenztriazole monohydrate (0.74 g, 4.8 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 mmol) in acetonitrile (10 mL) was added a solution of 3-(trifluoromethoxy) benzylamine 8(0.84 g, 4.4 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for overnight. The reaction mixture was concentrated in vacuo, and saturated aqueous NaHCO3solution was added to the residue. After extraction with ethyl acetate, the organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (0?10percent MeOH in CHCl3) to obtain 9(1.18 g, 98percent) as a colorless powder.1H-NMR (600 MHz, CDCl3) delta: 3.73 (3 H, s), 4.62 (2 H, d, J=6.0 Hz), 7.08?7.13 (1 H, m), 7.18 (1 H, s), 7.26?7.29 (1 H, m), 7.31?7.37 (2 H, m), 7.44?7.51 (1 H, m), 7.55 (1 H, d, J=1.4 Hz); MS ESI: m/z300 [M+H]+.

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:
Article; Yamamoto, Shuji; Ohta, Hiroshi; Abe, Kumi; Kambe, Daiji; Tsukiyama, Naohiro; Kawakita, Yasunori; Moriya, Minoru; Yasuhara, Akito; Chemical and Pharmaceutical Bulletin; vol. 64; 11; (2016); p. 1630 – 1640;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 760212-58-6, 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. 760212-58-6 name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[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.

SYNTHESIS EXAMPLE 1 (Synthesis of Compound 1); Into a 100-mL three-necked flask, 3.0 g (8.6 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 2.2 g (8.7 mmol) of bis(pinacolato)diboronic acid, 0.21 g (0.29 mmol) of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II), 2.5 g (25 mmol) of potassium acetate, and 50 ml of DMF were charged and the mixture was heated at 80 C for 3 h in argon flow. After confirming the disappearance of the starting boron compound, the mixture was cooled to room temperature. After adding 2.2 g (8.6 mmol) of 9-bromophenanthrene, 0.21 g (0.29 mmol) of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II), and 21 mL of a 2 M aqueous solution of sodium carbonate, the mixture was further heated at 80 C for 3 h under stirring. After the reaction, water was added. The precipitated crystals were corrected by filtration, washed with water and methanol, and dried under reduced pressure, to obtain a crude reaction product, which was then purified by a column chromatography (silica gel, dichloromethane: hexane), to obtain 2.5 g of white crystals. The obtained crystals were identified to Compound 1 by FD-MS (field desorption mass spectrometry). Yield: 65%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2236501; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-nitro-1H- imidazole (500 mg, 4.42 mmol) in DMSO (3 mL) was added but-3-en-2-one (465 mg, 6.63 mmol) followed by DMAP (32.4 mg, 0.265 mmol). The mixture was stirred at 70 C for 1.5 h. Water was added and extracted with EtOAc (3 x 50 mL). The organic layer was dried over Na2SO4 and concentrated to give 4-(4-nitro-1H-imidazol-1-yl)butan-2-one (420 mg, 2.293 mmol, 52 % yield). (2354) MS ESI m/z 184.0 (M+H)+ (2355) 1H NMR (499 MHz, CDCl3) delta 7.82 (d, J=1.5 Hz, 1H), 7.50 (d, J=1.4 Hz, 1H), 4.35 – 4.31 (m, 2H), 3.01 (t, J=6.0 Hz, 2H), 2.23 (s, 3H).

The synthetic route of 5-Nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); 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 305790-48-1 as follows. category: imidazoles-derivatives

5-bromo~l-(2,2-diraethylpropyl)-3-raethyl-l,3-dihydro-2H»benziraidazol-2~one (1-5)A solution of 6-bromo-l -methyl- 1, 3 -dihydro-2H-benzimidazol-2-one (1-4, 500 mg, 2.20 mmol) in DMF (10 ml) was treated with Sodium hydride (176 mg, 4.40 mmol, 2.0 eq) followed by the l-Iodo-2,2-Dimethylpropane (585 muEpsilon, 4.40 mmol, 2.0 eq). The reaction was irradiated at 175 deg C for 20 min in a microwave. The reaction was complete by LC/MS, so it was partitioned between EtOAc (2×125 ml) and water (150 ml). The combined organic layers were dried over Na SO4 and concentrated. The crude maroon-orange oil was purified via flash column chromatography (Si02: 100% Hex to 60:40 Hex:EtOAc), affording the title compound, 5-bromo-l-(2,2-dimethylpropyl)-3-methyl-l,3-dihydro-2H-benzimidazol-2-one (1-5), as a yellow solid with >95% purity. ‘HNMR (600 MHz, CDC13) delta 7.18 (dd, 1H, J= Hz), 7.10 (s, H), 6.88 (d, IH, J- Hz), 3.63 (s, 2H), 3.40 (s, 3H), 1.02 (s, 9H). LRMS m/z: Calc’d for C7H7Br 202 (M.+H) 232.1, found 232.8.

According to the analysis of related databases, 305790-48-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DUDKIN, Vadim; FRALEY, Mark, E.; ARRINGTON, Kenneth, L.; LAYTON, Mark, E.; RODZINAK, Kevin, J.; PERO, Joseph, E.; REIF, Alexander, J.; WO2012/21382; (2012); 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39021-62-0

n-BuLi (2.5 M in hexanes, 0.52 mL, 1.3 mmol) was added dropwise to a solution of 6-bromo-2,4-dichloro-3-phenylquinoline (353 mg, 1 mmol, Intermediate 1: step c) in dry THF (10 mL) in a 100 mL three necked round bottomed flask at -78 C. under N2. Stirring was continued for 30 minutes then a solution of 1-methyl-1H-imidazole-5-carbaldehyde (110 mg, 1 mmol) in dry THF (10 mL) was added at -78 C. The cooling bath was removed and the mixture was gradually warmed up to room temperature and stirred for 2 hours. The mixture was quenched by adding H2O (10 mL) and then extracted with CH2Cl2 (2*50 mL). The combined organic phase was dried over Na2SO4, concentrated to dryness and purified by prep-TLC (developed by CH3OH/CH2Cl2 1:5) to afford the title compound as a white solid. MS (ESI): 384.1 [M+H]+. 1H NMR (300 MHz, CD3OD) delta ppm 8.45 (s, 1H), 7.94 (dd, J=42.2, 8.0 Hz, 2H), 7.73-7.24 (m, 6H), 6.56 (s, 1H), 6.16 (s, 1H), 3.70 (s, 3H).

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 39021-62-0.

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

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. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5BrN2

To a solution of 5-bromo-1-(triphenylmethyl)-1H-benzimidazole and 6-bromo-1-(triphenylmethyl)-1H-benzimidazole (1:1 mixture) (6.0 g, 13.7 mmol) in toluene (30 mL), was added tetrakis(triphenylphosphine) palladium(0) (0.8 g, 0.7 mmol), followed by a solution of sodium bicarbonate (2.9 g, 34.2 mmol) in water (15 mL). A solution of 3-formylphenylboronic acid (2.3 g, 15.0 mmol) in ethanol (8 mL) was then added and the reaction was heated at reflux overnight. After cooling, the bulk of the solvent was removed in vacuo, and the residue was partitioned between ethyl acetate and water. The organics were washed with brine, dried (Na2SO4), and concentrated in vacuo. Chromatography of the residue on silica gel (35-50% EtOAc/hexanes) provided the product as an inseparable mixture of trityl regioisomers, 3-[1-(triphenylmethyl)-1H-benzimidazol-5-yl]benzaldehyde and 3-[1-(triphenylmethyl)-1H-benzimidazol-6-yl]benzaldehyde. (M+1) 465.2 ES, 3.01 min and 3.05 min (LC-MS Method A).

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; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, 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 10040-98-9, SDS of cas: 10040-98-9

A mixture of malonitrile (30.0 mg, 0.45 mmol) and 4-(1H-imidazol-1- yl)benzaldehyde (78.0 mg, 0.45 mmol) in anhydrous ethanol ( 4.0 mL) was charged with N- methylmorpholine (0.05 mL, 0.45 mmol) for 2 minutes. To the mixture was added 1-(4- fluorophenyl)-3-methyl-1H-pyrazol-5(4H)-one (90.0 mg, 0.45 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature for 48 hrs. The suspension was filtered under vacuum and off white solid was obtained. The solid was gently washed with hexanes (20 mL) and chilled ethanol (10 mL) and further dried under high vacuum to provide compound 44 as an off white solid (170 mg, 88%).1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.25 (s, 1H), 7.83-7.74 (m, 3H), 7.62 (d, J = 8.4 Hz, 2H), 7.40 (d, J = 8.4 Hz, 2H), 7.36-7.26 (m, 4H), 7.10 (s, 1H), 4.77 (s, 1H), 1.82 (s, 3H). MS (ESI): Calcd for C23H17FN6O: 412, found: 413 (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, 4-Imidazol-1-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; YU, Chengzhi; POLAT, Tulay; YAN, Chao; RABIZADEH, Shahrooz; THEODORESCU, Daniel; (108 pag.)WO2016/205460; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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. COA of Formula: C5H6N2O2

Step 1 Preparation of 1-trityl-1H-imidazole-4-carboxylic acid methyl ester A solution of 1H-Imidazole-4-carboxylic acid methyl ester (1.0 g, 7.93 mmol) in N,N-dimethylformamide at 25 C. was treated with triethylamine (2.2 mL, 15.86 mmol) and triphenylmethylchloride (2.43 g, 8.72 mmol). The reaction was stirred at 25 C. for 8 h and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with water, a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50:50 ethyl acetate/petroleum ether) afforded 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.88 g, 98.6%) as a white foam: 1H NMR (DMSO-d6, 300 MHz) delta7.56 (s, 1H), 7.47 (m, 10H), 7.09 (m, 6H), 3.69 (s, 3H).

The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dunten, Peter W.; Foley, Louise H.; Huby, Nicholas J.S.; Pietranico-Cole, Sherrie L.; Yun, Weiya; US2004/14766; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Chloro-1H-benzimidazole (7.5 g, 49 mmol) was dissolved in dimethylformamide (20 mL),and the reaction mixture was cooled to oo C. Sodium hydride ( 60% dispersion in mineral oil 2.16 g,5 5.4 mmol) was carefully added. The reaction mixture was stirred at ambient temperature for 1 hour,and after that iodomethane (8.37g, 59 mmol) was added. The reaction mixture was stirred at ambienttemperature overnight, and then water (200 mL) was added. The solid was collected by filtration toafford 5 g, 61% of the titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) o ppm 3.79(s, 3H), 7.21-7.33 (m, 2H), 7.58 (t, J=7.0 Hz, 2H).

The synthetic route of 2-Chloro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; GOMTSIAN, Artour; DEKHTYAR, Tatyana; FRANK, Kristine E.; FRIEDMAN, Michael M.; JOSEPHSOHN, Nathan; MOLLA, M-Akhteruzz; VASUDEVAN, Anil; NG, Teresa; SHAFEEV, Mikhail; WO2014/5129; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 29043-48-9, 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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: First, a mixture of 4-nitrobenzene-1,2-diamine (1 g) and formic acid (0.74 mL) in 5 N HCl (70 mL) was stirred and heated to reflux for 24 h. The mixture was cooled to room temperature and neutralized by 10% NaOH, and precipitate was isolated, recrystallised from water and dried to produce 5-nitrobenzoimidazole (0.69 g) [37]. Next, 5-nitrobenzoimidazole (0.25 g) was dissolved in ethanol (20 mL). The solution was stirred and heated to reflux, and the palladium-on-charcoal catalyst (0.15 g) and hydrazine hydrate (1.6 mL) were added. Then the mixture was stirred for 4 h, and filtered in hot. The filtrate was evaporated, and the residue was recrystallised from ethanol to give rise to the precursor compound 5-aminobenzoimidazole (0.163 g). Finally, a mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride (0.25 g), 5-aminobenzoimidazole (0.15 g) in isopropanol (25 mL) was stirred and heated to reflux for 4 h. The precipitate was filtered off, recrystallised from methanol and dried to afford 12 as yellow powder (0.32 g, yield 73%).

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-1H-benzoimidazol-5-ylamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Lue, Shuang; Zheng, Wei; Ji, Liyun; Luo, Qun; Hao, Xiang; Li, Xianchan; Wang, Fuyi; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 84 – 94;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem