Author: Jessica.F

Electric Literature of 3543-73-5, A common heterocyclic compound, 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, molecular formula is C14H19N3O2, 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-5 Preparation of Ethyl 4-{5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (III) Ethyl 4-[5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (II, 200.0 g, 0.763 mol) was added to DM Water (1.1 L). Aqueous sodium acetate.3H2O (20.0 g sodium acetate.3H2O in 100 mL DM water) and acetic acid (400 mL) was added and agitated till complete dissolution of compound of the formula II. The reaction mixture was cooled to 0-5 C. and ethylene oxide (270.0 g, 6.12 mole) was added maintaining the temperature of the reaction mixture at 0-5 C. The reaction mixture was stirred at 0-5 C. for 5 hours. The temperature of reaction mixture was raised to 20-25 C. and agitated at 20-25 C. for 18 hours. After completion of the reaction, dichloromethane (2.0 L) was added at 20-25 C. followed by addition of aqueous solution of potassium carbonate (440.0 g potassium carbonate in 1.1 L DM water) portion wise at 20-25 C. to control the evaluation of effervescence and agitated at 20-25 C. for 5-10 minutes. The layers were separated. The organic layer (dichloromethane) was washed with DM water (1.0 L) twice and organic layer was concentrated under vacuum at 40-50 C. till viscous mass is obtained. The viscous mass was dissolved in acetone (1.0 L), cooled to 0-5 C. and agitated at 0-5 C. for 1 hour. The solid separated out was filtered, washed with chilled (0-5 C.) acetone (200.0 mL) and dried at 40-50 C. under vacuum for 6 hours to give the title compound (III, 210.0 g; 78.53%), with a purity of 99.06%.

The synthetic route of 3543-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LIMITED; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; US2014/121383; (2014); A1;,
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

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

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

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

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

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-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 89830-98-8, Quality Control of 5-Cyclopropyl-1H-imidazole

[00400] A mixture of Example 61f (300 mg, 0.63 mmol), Example 61g (204 mg, 1.89 mmol), 8- quinoline (36 mg, 0.25 mmol), Cs2C03(411 mg, 1.26 mmol) and Cu20 (36 mg, 0.25 mmol)in BuCN (5 mL) was stirred at 120°C for 16 h under N2. Then the solution was filtrated and purified by Prep-HPLC, followed by Prep-TLC (DCM/MeOH= 20/1) to give thedesired product Example 61 (6.6 mg, yield 2percent) as a white solid. LCMS [M+l] + = 456.0. NMR (400 MHz, DMSO- 6) delta 11.25 (s, 1H), 8.67 (s, 1H), 8.04 (t, J= 7.9 Hz, 1H), 7.85 (t, J= 7.0 Hz, 2H), 7.76 (s, 1H), 7.62 (s, 1H), 7.34 (s, 1H), 7.10 (s, 1H), 4.37 (m, 2H), 4.25 (t, J= 8.5 Hz, 2H), 2.47 (m, 2H), 2.19 (s, 3H), 1.96 (m, 2H), 1.82 (m, 1H), 0.82-0.73 (m, 2H), 0.69 (d, J= 4.4 Hz, 2H).

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-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Imidazole-2-carboxylic acid ethyl ester 1 (100 mg, 0.71 mmol) was dissolved in 10 ml of THF, sodium hydride (43 mg, 1.78 mmol) was slowly added under an ice bath for activation for 1 h, and iodomethane (507 mg, 3.57 mmol) was added,After the addition, the reaction was performed at room temperature for 1h. TLC detection reaction is complete,Stop the reaction,Concentrate under reduced pressure to remove the solvent,Add water to dissolve,Ethyl acetate extraction (3×20ml),Combine organic layers,Wash with saturated saline,Dry over anhydrous sodium sulfate and filter,Concentrate to get crude product.Purified by column chromatography (PE:EA=1:1) to obtain yellow oily liquid,Compound 1-methyl-1H-imidazole-2-carboxylic acid ethyl ester 1b(98 mg, yield 89%).

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 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan University; Li Guobo; Wang Zhenling; (40 pag.)CN111187218; (2020); A;,
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

[0104] Compound 26: A mixture of Compound 25 (4- (diphenylamino)phenyl)boronic acid (900 mg, 3.1 mmol), Compound 9 (1.09 g, 3.1 mmol), Pd(PPh3)4 (180 mg, 0.16 mmol) and K2CO3 (1.38 g, 10 mmol) in 1,4- dioxane/H2O (25 mL/5 mL) was degassed and the resulting mixture was heated at about 100 0C overnight under an argon atmosphere. After cooling to room temperature, the resulting mixture was poured into water, extracted with ethyl acetate (100 mL x 2). The organic phase was dried over Na2SO4 and filtered. After addition of hexanes (100 mL), a yellow precipitate formed after about one hour. Filtration gave a yellow solid (760 mg) and the filtrate was absorbed on silica gel and purified by flash chromatography to give a yellow solid (200 mg). The total amount of product (Compound 26) was 960 mg in 62% yield.

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; NITTO DENKO CORPORATION; ZHENG, Shijun; CAYAS, Jensen; LI, Sheng; MOCHIZUKI, Amane; CHAF, Hyunsik; HARDING, Brett, T.; WO2011/8560; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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.

To a solution of 4-iomethyl-1H-imidazole (970 mg, 545 mmoles) in DMF (10 mL) is added NaH 60% dispersion inmineral oil (220 mg, 5.5 mmoles). The reaction mixture isheated at 50 C. for 1 h, then 2-bromoethylbenzene (781 f.LL,5.5 mmoles) and a catalytic quantity oftetrabutylammoniumbromide are added to the mixture. The reaction mixture is50 then heated at 80 C. for 5 hours. Half-saturated ammoniumchloride solution is added, and the aqueous phase is extractedthree times with Et20. The organic phase is washed withwater, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (heptane:AcOEt)as eluentwithagradientfrom (95:5)to (60:40)to give4-iodo-1-phenethyl-imidazole and 5-iodo-1-phenethyl-imidazole.4-iodo-1-phenethy 1-imidazole1H NMR: 7.38-7.15 (m, 4H), 7.10-6.96 (m, 2H), 6.93 (s,lH), 4.14 (t, J=8.5 Hz, 2H), 3.04 (t, J=8.5 Hz, 2H).5-iodo-1-phenethyl-imidazole1H NMR: 7.41 (s, lH), 7.36-7.18 (m, 3H), 7.15-7.00 (m,3H), 4.15 (t, J=8.6 Hz, 2H), 3.04 (t, J=8.6 Hz, 2H).

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; BIOPROJET; Berrebi-Bertrand, Isabelle; Billot, Xavier; Calmels, Thierry; Capet, Marc; Krief, Stephane; Labeeuw, Olivier; Lecomte, Jeanne-Marie; Levoin, Nicolas; Ligneau, Xavier; Robert, Philippe; Schwartz, Jean-Charles; (73 pag.)US9255101; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem