Author: Jessica.F

Synthetic Route of 17325-26-7, 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 17325-26-7 as follows.

To a mixture of methyl 1H-imidazole-4-carboxylate (2.0 g, 15.9 mmol) in DMF (30 mL), were added DIPEA (4.1 g, 31.72 mmol), then SEM-Cl (4.0 g, 23.4 mmol) dropwise. The reaction mixture was stirred at RT for 16 h, then quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography over silica gel (EtOAc in PE 30~50%, v/v) to give methyl 1-((2- (trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate as a colorless oil (2.13 g, 52%). LC-MS (ESI): m/z (M+1)+ = 257.21.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REMEDY PLAN, INC.; CRIMMINS, Gregory, Thomas; DE JESUS DIAZ, Dennise, Alexandra; BHURRUTH-ALCOR, Yushma; (483 pag.)WO2019/213570; (2019); 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. 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Intermediate 158 Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-((1-methyl-1H-imidazol-2-yl)methoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate [0988] Methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (Intermediate 28-29) (46.3 mg) and 2-(chloromethyl)-1-methyl-1H-imidazole (39.2 mg) were suspended in dimethylformamide (1.8 mL) and potassium carbonate (62 mg) was added. The reaction mixture was shaken for 24 h at 60 C. Another portion of 2-(chloromethyl)-1-methyl-1H-imidazole (39.2 mg) and potassium carbonate (62 mg) was added and the mixture was shaken again for 24 h at 60 C. and than directly chromatographed by HPLC on reversed phase. The product fractions are collected and lyophilized to give the title compound. Yield: 31.5 mg; LC (method 23): tR=1.54 min; Mass spectrum (ESI+): m/z=557 [M+H]+.

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; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (2013); 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. 3034-38-6, name is 5-Nitro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Nitro-1H-imidazole

General Procedure:To a solution of 3-chloro-1-phenylpropan-1-one (2, 2.0 mmol) in toluene (25-30 mL) was added azoles (3.0 mmol) and triethylamine (4.0 mmol) at room temperature. The reaction mixture was heated at reflux under stirring for 3-4h in an oil bath. Solvent was distilled off under reduced pressure and the residue was taken into ethyl acetate (20 mL). Organic layer was washed with water (10 mL x 3) and dried over sodium sulfate. Sodium sulfate was filtered off and washed with ethyl acetate (5 mL x 2). The combined filtrate was concentrated under reduced pressure to yield crude product which was purified by recrystallization with ethyl acetate/hexane to give 3-(substituted 1H- azol-1-yl)-1-phenylpropan-1-one (3-9).

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 3034-38-6.

Reference:
Article; Kumar, Lalit; Sarswat, Amit; Lal, Nand; Jain, Ashish; Kumar, Sumit; Kiran Kumar; Maikhuri, Jagdamba P.; Pandey, Atindra K.; Shukla, Praveen K.; Gupta, Gopal; Sharma, Vishnu L.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 176 – 181;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20485-43-2, 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 20485-43-2 as follows.

Example 16 rac-(3aR,14bR)-10-Cyclohexyl-N7-(dimethylsulfamoyl)-13-methoxy-N3a,N3a- dimethyl-2-((l-methyl-lH-imidazol-2-yl)carbonyl)-l,2,3,14b-tetrahydroindolo[2,l- a]pyrrolo[3,4-d][2]benzazepine-3a, 7(4H)-dicarboxamide. HATU (37.5 mg, 0.099 mmol) was added to a solution of rac-(3aR,14bR)-10-cyclohexyl-N7- (dimethylsulfamoyl)-13-methoxy-N3a,N3a-dimethyl-l,2,3,14b-tetrahydroindolo[2,l- alpha]pyrrolo[3,4-d][2]benzazepine-3a,7(4H)-dicarboxamide (30 mg, 0.049 mmol) and 1- methyl-lH-imidazole-2-carboxyIic acid (12.5 mg, 0.099 mmol) in DMF (1 mL) and TEA (0.03 mL, 0.2 mmol). The reaction mixture was stirred at rt for 16 h, diluted with MeOH, and purified by preparative HPLC (H2O/MeOH with 0.1% TFA buffer) to yield rac-(3aR,14bR)-10-cyclohexyl-N7-(dimethylsulfamoyl)-13-methoxy-N3a,N3a- dimethyl-2-(( 1 -methyl-1H-imidazol-2-yl)carbonyl)- 1 ,2,3 , 14b-tetrahydroindolo[2, 1 – alpha]pyrrolo[3,4-d][23benzazepine-3a,7(4H)-dicarboxamide (20.3 mg, 0.028 mmol, 57% yield) as a bright yellow solid. Complex mixture of rotamers was observed, partial 1H NMR (aromatic region) reported for 2 major rotamers (~3:2 ratio). 1H NMR (500 MHz, DMSO-d6) delta 6.78 (s, 0.6H), 6.91 (s, 0.4H), 7.00 (s, 0.4H), 7.05 (s, 0.4H), 7.08 – 7.22 (m, 2.2H), 7.32 (d, J= 8.2 Hz, 0.6H), 7.37 (d, J= 8.2 Hz, 0.4H), 7.54 (dd, J= 8.6, 1.2 Hz, 0.4H), 7.61 (dd, J= 8.6, 1.2 Hz, 0.6H), 7.81 (d, J= 8.6 Hz, 0.6H), 7.84 (d, J= 8.6 Hz, 0.4H), 8.09 (br s, 0.4H), 8.31 (br s, 0.6H), 11.31 (s, 0.4H), 11.69 (s, 0.6H). LCMS: m/e 716 (M+H)+, ret time 3.67 min, 4 minute gradient.

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; BRISTOL-MYERS SQUIBB COMPANY; WO2009/120733; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3314-30-5, 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. 3314-30-5 name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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.

To a solution of methyl diethylphosphonoacetate(3.17g, 15.0 mmol) in dry THF (40 mL) was added sodium carbonate (3.79 g, 27.4 mmol), the mixturewas stirred for 30 min at room temperature prior to the addition of compound 2 (2.0 g, 13.7 mmol).The mixture was stirred and refluxed for 24 h under an argon atmosphere and monitored by TLC.After complete conversion of starting material, the reaction mixture was filtered, the filtrate wasconcentrated and re-dissolved by ethyl acetate, and then washed with saturated NaCl solution anddried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash silica gel column(PE/EA = 4/1, v/v) to obtain 3 as white solid in 87.5% yield. LC-MS m/z: 203.1 [M + H]+.

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

Reference:
Article; Wang, Shuxiang; Guan, Lihong; Zang, Jie; Xing, Kun; Zhang, Jian; Liu, Dan; Zhao, Linxiang; Molecules; vol. 24; 7; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-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. Safety of Ethyl 1H-imidazole-2-carboxylate

(Reference Example 8) Synthesis of ethyl 1-(difluoromethyl)-1H-imidazole-2-carboxylate: Potassium carbonate (1.28 g, 9.28 mmol) and sodium chlorodifluoroacetate (1.31 g, 8.56 mmol) were added to a solution of ethyl 1H-imidazole-2-carboxylate (1.00 g, 7.14 mmol) in acetonitrile (35 mL) at room temperature and the resultant mixture was stirred at 60°C for 24 hours. Further, potassium carbonate (0.640 g, 4.63 mmol) and sodium chlorodifluoroacetate (0.660 g, 4.33 mmol) were added at room temperature and the reaction liquid was stirred at 80°C for 8 hours. The reaction liquid was cooled to room temperature and distilled water was added to the reaction liquid and the reaction liquid was extracted with ethyl acetate. The organic layer was washed with a 10percent aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate) to obtain ethyl 1-(difluoromethyl)-1H-imidazole-2-carboxylate (0.838 g, 4.41 mmol, 62percent) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 1.46 (3H, t, J=7.2 Hz), 4.47 (2H, q, J=7.2 Hz), 7.28 (1H, s), 7.53 (1H, d, J=1.6 Hz), 8.16 (1H, t, J=60.8 Hz).

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

Reference:
Patent; Toray Industries, Inc.; ARAI Tadamasa; MORITA Yasuhiro; UDAGAWA Shuji; ISEKI Katsuhiko; IZUMIMOTO Naoki; (95 pag.)EP3263565; (2018); 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 53710-78-4 as follows. Product Details of 53710-78-4

General procedure: 60% NaH (0.23 mmol) was added to a solution of 6a (0.23 mmol) in dry DMF (15 mL) at 0-5C. After stirring for 15 min at room temperature. 1-(3-chloropropyl)-1H-imidazole or 1-(4-chlorobutyl)-1H-imidazole (0.34 mmol) was added and stirred for 12 h at 60-65 C. After cooling, the mixture was poured into H2O (120 mL) and the resulting solution was extracted with ethyl acetate (60 mL × 3). The organic phase was combined, washed with brine (180 mL× 3), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate/MeOH (5:10:1, v/v) as eluent to afford 7d or 7e.

According to the analysis of related databases, 53710-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hu, Yuanyuan; Ruan, Wenchen; Gao, Anhui; Zhou, Yubo; Gao, Lixin; Xu, Meng; Gao, Jianrong; Ye, Qing; Li, Jia; Pang, Tao; Pharmazie; vol. 72; 12; (2017); p. 707 – 713;,
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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5BrN2

5-Bromo-1-methyl-1H-imidazole (6.66 g, 41.4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N2 atmosphere. The contents were cooled to 0 C. in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0 C. and a solution of N-methoxy-N-methylpyrimidine-2-carboxamide (3.09 g, 15.9 mmol, Intermediate 15: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C., then slowly warmed to room temperature, then heated to 40 C. in an oil bath and heated with stirring at that temperature for approximately 36 hours. The contents were then cooled to 0 C., quenched with a saturated aqueous NH4Cl solution, diluted with ethyl acetate and transferred to a reparatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgSO4, filtered, then distilled under reduced pressure to afford an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM/(10% of a 2 M NH3 MeOH in DCM)) to provide the title compound.

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; 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.; US2015/105404; (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. 13750-62-4, name is 1-Benzyl-2-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Computed Properties of C11H12N2

General procedure: 2.3. Typical procedure for the synthesis of imidazolium ion tethered TsDPENs 5a. A solution mixture of the intermediate 3 (818 mg, 1.5 mmol) and 1,2-dimethyl-1H-imidazole (173 mg, 1.8 mmol) in acetonitrile (2 mL) was heated at 70 C for 30 h. The solvent was removed under reduced pressure, and the residue was washed with a mixture solvent (hexane/ethyl acetate = 10:1) and dried in vacuo to give an intermediate 4a, to which HCl solution (3 mL, 4 M in dioxane) was added. The reaction mixture was stirred at room temperature for 5 h and the precipitation was filtered and washed with hexane to give the Boc deprotected intermediate, which was used for the next step directly without further characterization. The Boc-deprotected intermediate was subsequently neutralized by Na2CO3 (159 mg, 1.5 mmol) in MeOH (2 mL). The mixture was stirred for 5 h and the solvent was removed to dryness. The solid residue was dissolved in dry CH2Cl2 and filtered, and concentrated to give the product 5a as a white solid (550 mg, 68% yield for 2 steps).

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; Kang, Guowei; Lin, Silong; Shiwakoti, Atul; Ni, Bukuo; Catalysis Communications; vol. 57; (2014); p. 111 – 114;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic 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 570-22-9, name: 1H-Imidazole-4,5-dicarboxylic acid

General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

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; Kumar, Anuj; Banerjee, Somesh; Roy, Partha; Sondhi; Sharma, Anuj; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 501 – 504;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem