Category: imidazoles-derivatives

Electric Literature of 24134-09-6, 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. 24134-09-6 name is 5-Bromo-1,2-dimethyl-1H-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.

A solution of n-BuLi (4.0 mL, 10 mmol, 2.5 M solution in hexane) was slowly added to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (1.77 g, 10.2 mmol) in THF (70 mL) at -78 C. After addition, stirring was continued for an additional 30 minutes and N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (1.76 g, 10.1 mmol, Intermediate 1: step a, Procedure A) dissolved in THF (25 mL) was slowly added. An additional 6 mL of THF was used to complete the quantitative addition. The mixture was stirred at -78 C. for 5 minutes then warmed to room temperature and stirred for 1 hour. The solution was quenched with water and layers were separated. The aqueous layer was extracted with DCM and the combined organic extracts washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 6% MeOH/DCM) to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-dimethyl-1H-imidazole, and friends who are interested can also refer to 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.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-41-1, 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. 3034-41-1 name is 1-Methyl-4-nitroimidazole, 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.

[0280j To a solution of i-methyl-4-nitro-1H-imidazole (500 mg, 3.94 mmol) in MeOH (10 mL) was added Pd/C (50 mg). The mixture was stirred at rt for 16 h under hydrogen atmosphere. Then the mixture was filtered and the filtrate was concentrated in vacuo. The crude product (340 mg. yield: 89%) was used in the next step without further purification. ESI-MS (M+H): 98.1.

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

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2849-93-6,Some common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, molecular formula is C8H6N2O2, 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 mixture of lH-benzoimidazole-2-carboxylic acid (124 mg, 0.76 mmol) inDMF (5 mL) was added TEA (152 mg, 1.5 mmol) and HATU (347 mg, 0.92 mmol). The reaction mixture was stirred for 5 min and 2-azetidin-3-yl-3 -phenyl-pyridine hydrochloride (100 mg, 0.76 mmol) was added. The reaction mixture was stirred at RT overnight. The mixture was diluted with water (10 mL), and extracted with EtOAc (2 x 20 mL). The combined organic extracts were washed with water (5 mL) and brine (5 mL), dried over Na2S04, and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography to give (lH-benzoimidazol-2-yl)-[3-(3-phenyl-pyridin-2-yl)-azetidin-l-yl]-methanone (100 mg, 0.28 mmol, 59% yield) as a light yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzimidazole-2-carboxylic acid, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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 934-32-7, Safety of 1H-Benzo[d]imidazol-2-amine

General procedure: A solution of the selected heterocyclic starting material (1.00 mmol) in THF (10 mL) and a solutionof isopentyl nitrite (141 mg, 1.20 mmol) in THF (10 mL) were both pumped at a flow rate of 0.25 mLmin1 with a Vapourtech ?Easy MedChem V3? system, meeting at a PTFE T-piece and the outputflowing through a 10.0 mL coil reactor maintained at 120 C, giving a residence time of 20 min.The pressure of the system was maintained at 7 bar with a back-pressure regulator. For compoundswhere an isolated yield was reported: the output mixture was concentrated under reduced pressureto give an oil (or powder). The oil (or powder) was purified using column chromatography withvarious mixtures of ethyl acetate and hexane as the eluent, or by recrystallisation using methanol, togive isolated compounds that showed no impurities by NMR spectroscopy. For compounds where aconversion was reported (due to volatility of products), the output mixture was carefully concentratedunder a reduced pressure of 100 mbar for 10 min and the conversion was calculated by integration ofproduct peaks to a quantified internal standard (nitrobenzene).

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-Benzo[d]imidazol-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Roeder, Liesa; Nicholls, Alexander J.; Baxendale, Ian R.; Molecules; vol. 24; 10; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 103057-10-9, A common heterocyclic compound, 103057-10-9, name is 4-(Chloromethyl)-1-trityl-1H-imidazole, molecular formula is C23H19ClN2, 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.

EXAMPLE 45 Methyl Z-4-[[2-butyl-5-[[1-butyl-3-(1H-imidazol-5-ylmethyl)-2,5-dioxo-4-imidazolidinylidene]methyl]-1H-imidazol-1-yl]methyl]benzoate monohydrochloride To a solution of methyl Z-4-[[2-butyl-5-[(1-butyl-2,5-dioxo-4-imidazolidinylidene) methyl]-1H-imidazol-1-yl]methyl]benzoate hydrochloride (0.237 g, 0.50 mmol) in DMF (3 mL) is added K2 CO3 (0.350 g, 2.54 mmol). After stirring for 5 minutes 4-(chloromethyl)-1-(triphenylmethyl)-1H-imidazole (0.250 g, 0.70 mmol) is added. The mixture is stirred for 16 hours, diluted with ethyl acetate, washed with water and brine and then dried over MgSO4. A viscous oil is obtained upon chromatography on silica gel (eluant 0.5% methanol in chloroform) and evaporation of the solvents in vacuo. This oil is dissolved in methanol (80 mL) and treated with acetic acid (30 mL). After heating at 90 C. (oil bath temp.) for 4 hours the solution is cooled and treated with water (10 mL) and hexanes (100 mL). The aqueous organic layer is separated and evaporated. This solid is redissolved in ethyl acetate/methylene chloride and washed with pH 7 buffer, dried over MgSO44 and evaporated in vacuo. The hydrochloride salt is then prepared by dissolving this solid in methanol and treating with ethereal HCl. Evaporation in vacuo of this solution and crystallization (2-propanol/ether) affords the required compound. Anal. Calcd. for C28 H34 N6 O4. 2HCl. H2 O: C, 55.17; H, 6.28; N, 13.79. Found: C, 54.88; H, 6.13; N, 13.24. mp 202-205 C.; MS (EI) 518.

The synthetic route of 103057-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US5308853; (1994); 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. 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, A new synthetic method of this compound is introduced below., Recommanded Product: 360-97-4

(c) 4-f(2-Meth.yl-2-propoxypropyl)amino]–lH-imidazole-5-carboxamide; The reaction mixture of 2-methyl-2-propoxypropanal, which was obtained from Example 2(b), (1.0 g, 8.3 mmol), 5-amino-4-irnidazolecarboxamide (0.5 g, 4.0 mmol), sodium cyanoborohydride (0.25 g, 4.0 mmol) and acetic acid (0.45 mL, 7.9 mmol) in 10 mL of methanol was stirred at ambient temperature for 1 h. The solvent was removed in vacuo. Water (20 mL) and ethyl acetate (20 mL) were added. The organic phase was separated and the solvent was removed in vacuo. Purification by ISCO flash (EtOAc:Heptane, gradient elution 1:1 to 100% EtOAc) gave 0.19 g (20 %) of the title compound. 1R NMR (CDCl3) delta ppm 6.98 (s, IH), 6.39 (br s, IH), 3.40 (t, 2H, J=6.7 Hz), 3.14 (d, 2H, J=4.3 Hz), 1.56-1.65 (m, 2H), 1.22 (s, 6H), 0.95 (t, 3H, J=7.5 Hz); MS (ESI) m/z 241 (M+l).

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; ASTRAZENECA AB; WO2007/142576; (2007); 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. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4ClN3O2

Methanamine (2M in THF, 15 mL) was added to a sealable tube containing 2-chloro-5-nitro- 1 H-benzo[d]imidazole (1 g). The reaction flask was sealed and stirred at 80 C for 16 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was washed with diethyl ether (15 mL) and dried in vacuo to afford the crude title product as a black tar (600 mg), which was used directly without purification. LCMS m/z 193.06 (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 5955-72-6.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

Step 1. 4-Iodo-l-methyl-lH-imidazole and 5-iodo-l-methyl-lH-imidazole (1205) [00394] Under an atmosphere of nitrogen at 0 C, a solution of 4-iodo-lH-imidazole (5.82 g, 30.00 mmol) in THF (50 mL) was treated with portionwise addition of sodium hydride (60% dispersion in mineral oil, 1.44 g, 36.00 mmol). After stirring for 30 min at 0 C, iodomethane was added (2.8 mL, 45.00 mmol) and the mixture was stirred for 1 h at 0 C. The reaction mixture was poured into water (100 mL) and was extracted with EtOAc (2 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 6.24 g (90%) of a -3 : 1 mixture of 4-iodo-l-methyl-lH-imidazole and 5- iodo-1 -methyl- lH-imidazole as a light yellow solid. MS (ESI) m/z 209 [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, 5-Iodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 71759-89-2, These common heterocyclic compound, 71759-89-2, name is 5-Iodo-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.

Step 1 To a solution of 113a (Synthonix, 5.0 g, 25.8 mmol) in THF (100 mL) at 0C is added portion wise NaH (60% in oil, 1.13 g, 28.3 mmol). The reaction is warmed to RT for 30 min and then cooled to 0C. EtBr is added and the reaction is stirred for 1 h at 0C, and then warmed to RT. The reaction is diluted ammonium chloride (10 mL) and NaHC03 (saturated) is added. The aqueous phase is extracted with EtOAc (100 mL). The organic layer is washed with water (2 x 20 mL), brine, dried (MgS04), filtered and concentrated under reduced pressure. Purification by chromatography (40-100% EtOAc/Hexanes) affords imidazole 113b.

Statistics shows that 5-Iodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-89-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STURINO, Claudio; BEAULIEU, Pierre; DEROY, Patrick; DUPLESSIS, Martin; JAMES, Clint; LACOSTE, Jean-Eric; MINVILLE, Joannie; MORENCY, Louis; MORIN, Sebastien; SIMONEAU, Bruno; TREMBLAY, Martin; WO2013/91096; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1,Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

1-Methyl-4-imidazolecarboxylic acid (4-1) (265 mg, 2.1 mmol)Was dissolved with N, N-dimethylformamide (12 mL)N-Methylmorpholine (850 mg, 8.4 mmol) was added with stirring,The reaction solution was placed in an ice water bath and slowly stirred for 10 minutes,Trimethylacetyl chloride (277 mg, 2.3 mmol) was then slowly added dropwise,Complete addition the reaction was stirred for 30 minutes under ice-water bath maintained;After the anhydride is completely formed,Under ice-cooling, a solution of 1- (4-methoxyphenyl) -3-methyl-2-piperazinone hydrochloride (4 -2) (462 mg, 1.8 mmol)Plus,The reaction was stirred at room temperature for 1 hour, followed by monitoring the reaction; After the reaction was completed, quenched with water, the reaction was concentrated in vacuo, the concentrate was extracted with dichloromethane, and then washed with saturated brine, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure.The concentrate was subjected to column chromatography to obtain a white solid1- (4-methoxyphenyl) -3-methyl-4- (1-methyl- 4- carbonylimidazole) piperazin- 2-one (compound- 4),Yield 70percent,

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujian Jinle Pharmaceutical Technology Co., Ltd.; Zhou Zhongxiang; Xing Yuanyuan; Chen Yingzhong; Deng Chengjun; Deng Honggui; Xue Wanhua; Zhang Shuzu; Chen Weipeng; Li Fang; (27 pag.)CN107174584; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem