Month: August 2021

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

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

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

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

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

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-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 33468-69-8, SDS of cas: 33468-69-8

Example 5: Preparation of Compound 25A microwave vial was charged with Intermediate F (20 mg, 0.044 mmol), 4-(trifluoromethyl)- lH-imidazole (20 mg, 0.15 mmol), CS2CO3 (43.2 mg, 0.133 mmol) and DMA (500 mu). The mixture was heated at 150C under microwave irradiation for 3 h. The mixture was then purified by reverse-phase preparative HPLC (0: 100 to 95 :5 MeCN:water: 0.1% v/v TFA modifier) to afford 1-25 as the TFA salt. ‘H NMR (500 MHz, DMSO-d6) delta = 8.68-8.20 (m, 4H), 5.00 (s, 1H), 4.55-4.38 (m, 1H), 4.22-4.16 (m, 1H), 4.12 (q, 3=1 A, 2H), 3.35-3.24 (m, 1H), 3.22-3.01 (m, 2H), 2.33-2.21 (m, 1H), 2.21-2.09 (m, 1H), 1.30 (d, /=6.9, 5H), 1.24 (t, /=7.2, 3H). MS (EI) Calc’d for C20H24F3N10 [M+H]+, 461; found 461.

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; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; FONG, Kin Chiu; ANTHONY, Neville John; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; LI, Chaomin; TIAN, Yuan; MU, Changwei (Charles); YE, Baijun; SHI, Feng; ZHAO, Xiaoli; FU, Jianmin; WO2015/188369; (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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17325-26-7

b) 3-(3-Acetoxy-7-chloro-2,2-dimethyl-indan-1 -yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of acetic acid 4-chloro-3-hydroxy-2,2-dimethyl-indan-1-yl ester (1.55 g, 6.1 mmol) in THF (30 mL) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 1.53 g, 12.2 mmol), and triphenylphosphine (3.2 g, 12.2 mmol). The reaction is cooled to 0 0C and di-f-butyl azodicarboxylate (2.81 g, 12.2 mmol) is added. The reaction is placed at room temperature and permitted to stir for ca. 12 hours and then is heated to 40 0C for 1.5 hours. The reaction mixture is cooled to 0 0C, quenched with 4 N HCI in dioxane (20 ml_, 80 mmol), and stirred for 30 minutes. The reaction is concentrated to near dryness and diluted with ethyl acetate. The organic layer is extracted three times with 1 N aqueous HCI. The aqueous extracts are combined, neutralized with Na2CO3, and extracted three times with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1 :3) to furnish 3-(3-acetoxy-7-chloro-2,2-dimethyl-indan-1- yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 332.04 (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 17325-26-7.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, HPLC of Formula: C19H13BrN2

A mixture of compound 1a (1.745 g, 5.0 mmol),(1.91 g, 7.5 mmol) and KOAc (1.47 g, 15.0)Was dissolved in anhydrous 1,4-dioxane (40 mL)After nitrogen replacement,Pd (dppf) Cl2 (0.18 g, 0.25 mmol) was added,Heated to reflux for 3h.After completion of the reaction, the mixture was cooled to room temperature, the mixture was poured into water and extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4 and the solvent was removed by steaming.The final crude product was purified using n-hexane / ethyl acetate (v / v = 1: 3) SiO2 column,A white powdery solid was obtained.Yield: 1.88 g, 95%.

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, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China University of Mining and Technology; Ni Zhonghai; Zhang Ran; Zhang Lifang; Zhao Yun; (20 pag.)CN106905242; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4, SDS of cas: 288-32-4

Step A: 4-chloro-1H-imidazole To a solution of 1H-imidazole (10.0 g, 0.15 mol) in chloroform (100 mL) was slowly added a solution of chlorine (2.08 g, 0.0294 mol) in chloroform (18.6 mL). The reaction was cooled to 0 C., then left stirring overnight, gradually warming to room temperature. Aqueous sodium bisulfite was added and the layers were separated. The aqueous was extracted with ethyl acetate (3*100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-10% methanol/dichloromethane) gave 4-chloro-1H-imidazole (400 mg) as a light yellow solid. 1H NMR (400 MHz, CD3OD, delta): 7.58 (s, 1H), 7.05 (s, 1H).

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; PFIZER INC.; US2012/202834; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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. Product Details of 4857-06-1

(5) 0.078 mol of 2-chlorobenzimidazole was dissolved in 90 mL of dry N,N-dimethylformamide, and 0.079 mol of 60% sodium hydrogen was added in portions in an ice bath and under a nitrogen atmosphere, followed by an ice bath. Stir for 30 minutes under nitrogen atmosphere, add 0.079 mol of 2-(trimethylsilyl)ethoxymethyl chloride, react at 20C for 16 hours, and turn the reaction solution into a yellow suspension, ice bathUnder cooling, 200 mL of water was slowly added, extracted with ethyl acetate, the organic phases were combined, and after drying, petroleum ether: ethyl acetate was used as eluent at a volume ratio of 10:1 to separate 16 g of white solid compound VII. The yield was 71.93%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4857-06-1, its application will become more common.

Reference:
Patent; Tierxi (Nanjing) Pharmaceutical Research And Development Co., Ltd.; He Xu; Hu Yongzhu; Zhang Chi; Liu Chun; Cui Xilin; (26 pag.)CN107663192; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem