Category: imidazoles-derivatives

934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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. Recommanded Product: 934-32-7

In a 50 mL single-mouth eggplant bottle, 0.55 g (4.1 mmol) of 1H-benzo[d]imidazol-2-amineDissolve in 15 mL of acetone, add 0.70 g (12 mmol) of potassium hydroxide powder and 1.1 g (8.2 mmol) of potassium carbonate, stir at room temperature for 10 min, transfer to ice water bath, add 0.45 mL (4.5 mmol) 2-iodopropane dropwise, and move to Stir in a 65 C oil bath for 3 h.The reaction was detected by TLC, the reaction solution was diluted with EA, the solid was filtered off, the solvent was evaporated, the solvent was evaporated, 10 mL of water was added, and extracted with EA (8 mL*3, combined organic phase, dried over Na2SO4, concentrated, flash silica gel column chromatography (gradient wash) De DCM: MeOH = 100:1 to 30:1) to give 275 mg of pale yellow solid.Yield 38%

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Anyanren Pharmaceutical Technology Co., Ltd.; Xie Dexun; Li Quanwei; Xue Weicai; Liu Hui; (27 pag.)CN108912095; (2018); A;,
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Synthetic Route of 106429-59-8, The chemical industry reduces the impact on the environment during synthesis 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, I believe this compound will play a more active role in future production and life.

To the solution of the crude product from Step 6 in MeOH (2 mL) was added NaOAc (14 mg), and 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde (21 mg). The resulting mixture was stirred at RT for 15 min, at which point NaCNBH3 (15 mg) was added to the solution. The resulting mixture was heated at 50 oC overnight to give a clear solution, which was purified directly by preparative RP-HPLC method E to give 5- fluoro-N-isopropyl-N-methyl-2-(1-(1-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5- yl)methyl)piperidin-3-yl)-2-thioxo-1,2-dihydro-3H-imidazo[4,5-c]pyridin-3- yl)benzamide as a TFA salt (1.20 mg); LCMS method B: Rt = 0.54 min; (M+H)+ = 574.6; 1H NMR (MeOH-d4): delta 9.01 (br, 1 H), 8.51 (s, 1 H), 8.21 (s, 1 H), 7.74 (s, 1 H), 7.38- 7.04 (m, 5 H), 4.65 (m, 1 H), 4.48 (m, 1 H), 4.31 (m, 2 H), 3.83 (m, 4 H), 2.87 (m, 2 H), 2.52 (m, 1 H), 2.15 (m, 3 H), 1.99 (m, 1 H), 1.32-0.82 (m, 6 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, 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 33543-78-1

Ethyl 1H-imidazole-2-carboxylate (4 g, 28.5 mmol), p-chlorobenzylchloride (4.38 mL, 34.3 mmol), and sodium carbonate (3.63 g, 34.3 mmol), was dissolved in DMF (8 mL).The solution was stirred at rt for 24 h, at which time water was added and material was extracted with EtOAc.The organic phase was collected, dried over magnesium sulfate, and decanted.Purification accomplished via silica gel flash chromatography (150 g silica, 10percent EtOAc/Hexanes to 80percent EtOAc/Hexanes.) The title compound was obtained as a clear, yellow-tinted oil. (Yield: 7.28 g, 27.5 mmol, 96percent) 1H NMR (400 MHz, CDCl3) 7.25, 7.15, 7.10-7.00, 5.55, 4.34, 1.36

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; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; US2012/252807; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 35445-32-0, 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 35445-32-0 as follows.

ethyl [2-BROM-1,] [4-DIMETHYL-1] H-imidazole-5-carboxylate To a solution of intermediate 93 (1.69 [G,] 0.01 mol) in CH3CN (60 mL) was added [NBS (2.15 G, 1.2 EQ. ) AND THE REACTION WAS STIRRED AT RT FOR 1 NIGHT. AFTER EVAPORATION] of the solvant, the residue was dissolved in DCM and washed with water. The organic layer was dried over [NA2SO4] and evaporated off. After purification by flash chromatography using DCM/MeOH 90/10 as eluent, the title compound was obtained as yellow crystals (0.645 g, 2.6 [MMOL)] in 26percent yield ;’H NMR [(CDC13,] 300 MHz) [S] 4.55 (q, 2H), 4.09 (s, 3H), 2.69 (s, 3H), 1.61 (t, 3H)

According to the analysis of related databases, 35445-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/6922; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. SDS of cas: 1849-01-0

A mixture of (±)-trans-N-(6-bromo-8-chloro-3-isoquinolyl)-2-cyano-cyclopropanecarboxamide (200 mg, 0.57 mmol), 1-methyl-2-benzimidazolinone (120 mg, 0.81 mmol), Pd3(dba)2 (100 mg, 0.11 mmol), Xantphos (130 mg, 0.22 mmol) and K3PO4 (360 mg, 1.7 mmol) in 1,4-dioxane (15 mL) was heated at 90 C. for 3 h under Ar. The mixture was concentrated and purified by silica-gel column chromatography (EA:PE=1:3 to 1:2) to give (±)-trans-N-[8-chloro-6-(3-methyl-2-oxo-benzimidazol-1-yl)-3-isoquinolyl]-2-cyano-cyclopropanecarboxamide (120 mg, 50% yield) as a yellow solid. LCMS (ESI) [M+H]+=418.1

The synthetic route of 1-Methyl-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-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.

Example 135 (S,Z)-N-(1-(2-chloro-6-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)pyrrolidin-3-yl)-1-methyl-1H-imidazole-2-carboxamideTo a 50 mL vial charged with a magnetic stir bar was added (S,Z)-5-(2-(3-aminopyrrolidin-1-yl)-3-chlorobenzylidene)thiazolidine-2,4-dione (75 mg, 0.23 mmol) (Example 86), 1-methyl-1H-imidazole-2-carboxylic acid (87 mg, 0.69 mmol), HATU (220 mg, 0.58 mmol) and dichloromethane (5 mL). Hunig’s base (0.202 mL, 1.16 mmol) was then added and the mixture was stirred at rt for 4 h. The reaction was then diluted with dichloromethane and washed with water. The mixture was separated with a phase separator tube and the organic phase was evaporated to dryness. The residue was purified by reverse phase chromatography to afford the title compound as a yellow solid (21 mg, 21%). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.89 (s, 1H) 7.51 (dd, 1H) 7.41 (dd, 1H) 7.18-7.27 (m, 2H) 7.01 (s, 1H) 4.67-4.77 (m, 1H) 4.00 (s, 3H) 3.63-3.75 (m, 2H) 3.47-3.54 (m, 1H) 3.36-3.47 (m, 1H) 2.39-2.51 (m, 1H) 2.14 (dd, 1H); m/z 432.

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

Reference:
Patent; ASTRAZENECA AB; US2011/218182; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2963-77-1,Some common heterocyclic compound, 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, molecular formula is C13H11N3, 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: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8).

The synthetic route of 2963-77-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; L’abbate, Fabrizio P.; Mueller, Ronel; Openshaw, Roxanne; Combrinck, Jill M.; de Villiers, Katherine A.; Hunter, Roger; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 243 – 254;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, 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 3543-73-5, Computed Properties of C14H19N3O2

Example-5 Preparation of Ethyl 4-{5-[bis(2-hydroxyethyI)amino]-l-methyl-lH-benzimidazol- 2-yl} butanoate (III) Ethyl 4-[5-amino-l -methyl- l H-benzimidazol-2-yl)butanoate (II, 200.0g, 0.763mol) was added to DM Water (1.1L). Aqueous sodium acetate.3H20 (20.0g sodium acetate.3H20 in lOOmL DM water) and acetic acid (400mL) was added and agitated till complete dissolution of compound of the formula II. The reaction mixture was cooled to 0-5C and ethylene oxide (270. Og, 6.12mole) was added maintaining the temperature of the reaction mixture at 0-5C. The reaction mixture was stirred at 0-5C for 5 hours. The temperature of reaction mixture was raised to 20-25C and agitated at 20-25C for 18 hours. After completion of the reaction, dichloromethane (2.0L) was added at 20-25C followed by addition of aqueous solution of potassium carbonate (440. Og potassium carbonate in 1.1L DM water) portion wise at 20-25C to control the evaluation of effervescence and agitated at 20-25C for 5-10 minutes. The layers were separated. The organic layer (dichloromethane) was washed with DM water (1.0L) twice and organic layer was concentrated under vacuum at 40-50C till viscous mass is obtained. The viscous mass was dissolved in acetone (1.0L), cooled to 0-5C and agitated at 0-5C for 1 hour. The solid separated out was filtered, washed with chilled (0-5C) acetone (200.0mL) and dried at 40-50C under vacuum for 6 hours to give the title compound (III, 210.0g; 78.53%), with a purity of 99.06%.

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, Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LTD.; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; WO2013/46223; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, molecular formula is C45H44N6O3, 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: C45H44N6O3

Example 5; Preparation of trityl olmesartan medoxomilTo dimethyl sulphoxide (800 ml), sodium hydroxide powder (50 gms) was added under nitrogen atmosphere and stirred at 20-250C for 10 minutes. To this, 4-( 1 -hydroxy- 1- methylethyl)-2-propyl-imidazole-5-ethyl carboxylate (100 gms) was added at 20-250C. 5- (4′-bromomethyl-biphenyl)-2-yl-1 -trityl tetrazole (270 gms) was added slowly at 20-250C, and the reaction mass was stirred at 20-250C for 12 hours. Further 10% sodium hydroxide solution (100 ml) was added to the reaction mass at 20-250C. The temperature of the reaction mass was raised to 40-450C, the contents stirred at 40-450C for 2 hours and 5- methyl-2-oxo-1 ,3-dioxane-4-yl)methyl chloride (160 gms) was added slowly at 45-5O0C over a period of 45 minutes. The contents were stirred at 45-5O0C for 2 hours. The reaction mass was then cooled to 0-50C, stirred for 1 hour at 0-50C, filtered and slurried in water (1.0 It) at 40-450C for 1 hour, filtered at 4O0C and dried at 4O0C. To the dried material, ethyl acetate (2.5 It) was added, heated to 50-550C for complete dissolution, ethyl acetate was distilled off to 1.0 It stage under vacuum at 45-5O0C. The contents were cooled to 0-50C, stirred at 0-50C for 3 hours, filtered, washed with chilled methanol (100 ml) and dried under vacuum at 40-450C to give 250 gms of the title compound. Purity by HPLC : > 99%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 144690-33-5, its application will become more common.

Reference:
Patent; CIPLA LIMITED; CURTIS, Philip, Anthony; WO2008/43996; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 96797-15-8, These common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-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.

d) Rac-(2-Ethyl-6-methyl-phenyl)-( 1-trityl- lH-imidazol-4-yl)-methanolThis compound was prepared using methodology described in J. Org. Chem. 1991, 56, 5739-5740. To a stirred suspension of 1.47 g (3.37 mmol) 4-iodo-tritylimidazole in 5 ml dichloromethane was added dropwise 1.12 ml (3.37 mmol) of a 3 M solution of ethylmagnesium bromide in diethyl ether at such a rate that the temperature of the reaction mixture did not rise above 28 0C. The resulting solution of ( 1-trityl- IH- imidazo 1-4- yl) -magnesium halide was stirred at room temperature for 30 minutes, and then a solution of 0.50 g (3.37 mmol) 2-ethyl-6-methyl-benzaldehyde in 2 ml dichloromethane was added dropwise over 10 minutes. The reaction mixture was then stirred at room temperature for 5 h, before being quenched by dropwise addition of water and diluted with dichloromethane. The phases were separated and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo to afford 1.40 g (90%) of the title compound as an off-white foam which was used in the next step without further purification.

Statistics shows that 4-Iodo-1-trityl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 96797-15-8.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/85556; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem