Month: August 2021

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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-1H-imidazole

General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.

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:
Review; Yang, Bin; Hird, Alexander W.; Russell, Daniel John; Fauber, Benjamin P.; Dakin, Les A.; Zheng, Xiaolan; Su, Qibin; Godin, Robert; Brassil, Patrick; Devereaux, Erik; Janetka, James W.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4907 – 4911;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10040-98-9, 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 10040-98-9 as follows.

General procedure: A mixture of azolyl ketone (1a/1b) (1 mmol) and aryloxy benzaldehyde (2a-f) (1 mmol) were dissolved in 10% NaOH-EtOH (5 mL), it was stirred at room temperature for 9-10 h. After completion, 5 mL water was added to the reaction mixture. The separated solid compound was filtered and washed with water. It was purified by crystallization with methanol/chloroform or basic alumina column chromatography to give the desired compounds (3-13).The compounds (16-31) were prepared by the reaction of their corresponding aldehyde and ketone partners.

According to the analysis of related databases, 10040-98-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Marrapu, Vijay K.; Chaturvedi, Vinita; Singh, Shubhra; Singh, Shyam; Sinha, Sudhir; Bhandari, Kalpana; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4302 – 4310;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

89830-98-8, name is 5-Cyclopropyl-1H-imidazole, 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. Product Details of 89830-98-8

To a flask were added 2-chloro-5-fluoro-4-iodopyridine (23.0 g, 89.3 mmol), 4-cyclopropyl-1H-imidazole (29.0 g, 268 mmol), potassium carbonate (30.8 g, 223 mmol), cuprous iodide (340 mg, 1.79 mmol), 8-hydroxyquinaldine (569 mg, 3.57 mmol) and dimethylsulfoxide (80 mL) under nitrogen. The mixture was heated to 90 C and stirred overnight. The resulting mixture was cooled to rt naturally and quenched with water (100 mL) and then extracted with EtOAc (200 mL x 2). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous Na2SO4. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (DCMIEtOAc (V/V) = 10/1-5/1) to give the title compound as a yellow solid (4.50 g, 2 1%).?HNIVIR(400MH4 CDCl3)8.40(d,J=2.7H4 1H), 7.92 (s, 1H), 7.38 (d,J= 5.4 H4 1H), 7.11 (s, 1H), 1.96-1.82 (m, 1H), 0.96 – 0.87 (m, 2H), 0.86- 0.80 (m, 2H?).

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; YANG, Xinye; PAN, Shengqiang; MA, Facheng; ZHANG, Yingxun; WANG, Xiaojun; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (105 pag.)WO2019/34096; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 52099-72-6, 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 7; Ethyl 4-(3-isopropenyl-2-oxo-2.3-dihydro-1H-benzimidazol-1-yl)butanoate; A mixture of the compound of Preparation 8 (114.0 g, 0.7 mol), potassium carbonate (136 mg, 1 mol) and the compound of Preparation 166 (167.4 g, 0.9 mol) in acetone (500 ml) was heated under reflux for 18 h. The reaction mixture was then cooled to room temperature and filtered, washing through with acetone (250 ml). The filtrate was concentrated in vacuo and the residue was dried overnight at 40C to give the title compound (223.8 g).1H-NMR (d6-DMSO): 1.10 – 1.20 (3H), 2.10 – 2.15 (3H), 3.95 – 4.07 (2H), 5.10 – 5.12 (1 H), 5.35 – 5.39 (1 H), 7.00 – 7.10 (3H), 7.20 – 7.26 (1 H)

The chemical industry reduces the impact on the environment during synthesis 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; WO2008/44127; (2008); 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 36947-68-9 as follows. name: 2-Isopropyl-1H-imidazole

To a slightly yellow homogeneous solution of 2-isopropylimidazole (10.000 g; 90.778 mmol) in dioxane (155 ml) and distilled water (155 ml) was added successively, at rt (in one portion), sodium carbonate (28.865 g; 272.333 mmol), and iodine (50.688 g; 199.711 mmol). The resulting brown heterogeneous reaction mixture was further stirred at rt, under nitrogen, for 24h. EA (450 ml) was then added followed by an aq. solution of sodium thiosulfate (27 g Na2S2O3 in 270 ml of water). The yellow homogeneous organic layer was separated and additionally washed with an aq. solution of sodium thiosulfate (18 g Na2S2O3 in 180 ml of water), and finally with brine (130 ml). The yellow organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give the pure product 4, 5-diiodo-2-isopropyl-1 /-/-imidazole as a yellow solid which was further dried under HV (31.810 g; 97%). LC-MS: tR = 0.62 min.; [M+H]+ = 363.19 g/mol.

According to the analysis of related databases, 36947-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/78291; (2008); 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. 16042-25-4, name is 2-Imidazolecarboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 16042-25-4

HATU (0.16 g, 0.43 mmol) was added to a solution of 3-chloro-5-({6-chloro-2-fluoro- 3-[(methylamino)methyl]phenyl}oxy)benzonitrile (0.10 g, 0.30 mmol) and 1 H- imidazole-2-carboxylic acid (0.05 g, 0.43 mmol) in DMF (3 ml.) and the solution was stirred at RT overnight. After 16 h, ethyl acetate (100 ml) and saturated NaHCOs solution (100 ml) were added. The organic layer was separated, washed with saturated NaHCOs solution (2 x 100 ml), brine (150 ml_), dried over MgSO4, filtered and concentrated. The crude material was purified by Reverse Phase HPLC to give the title compound (0.025 g, 20%) as a white solid. 1H NMR (400 MHz, DMSO-c/6) delta ppm 7.82 (s, 1 H), 7.46 – 7.57 (m, 3 H), 7.27 – 7.37 (m, 2 H), 7.18 (s, 1 H), 5.57 (s, 1 H), 4.77 (s, 1 H), 3.53 (s, 1.5 H), 2.98 (s, 1.5 H). 19F NMR (376 MHz, DMSOd6) delta ppm -75.19 (s, 1 F). LCMS m/z 418 (M-1 ).

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; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); 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. 30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

A solution of the methylimidazole (3.2 mL, 40.0 mmol) in 30 mL de CH3CN:Et3N (2:1) was cooled to -30 C and quickly added to a previously prepared solution of ethyl chloroformiate (7 mL, 66.0 mmol) in 10 mL of CH3CN. The mixture was stirred for 15h at rt. The solvents were removed under reduced pressure; the crude was re-dissolved in water (20 mL) and extracted with chloroform (3 × 20 mL). The organic fractions were dried and concentrated, and the resulting residue was purified by flash cromatography (aluminum oxide, 90% MeOH) to give 3.72 g of a crude ester residue which was directly used for the next step. A solution of this residue (1.5 g, 9.74 mmol) in 15 mL of aqueous NaOH (1 M) was refluxed for 1 h. The resulting mixture was acidified to pH 2.0 using HCl 10% (aprox.15 mL) and lyophilized. The crude was dissolved in MeOH and concentrated underreduced pressure to give 12 as a slighlty pink solid (1.2 g, 98%).

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 30148-21-1.

Reference:
Article; Jimenez-Balsa, Adrian; Dodero, Veronica I.; Mascarenas, Jose L.; Tetrahedron; vol. 69; 36; (2013); p. 7847 – 7853;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

COMPOUND 12.1.59: 4-{7-(CYCLOBUTYLOXY)-6-METHOXY-2-[(5-METHYL- 1H-IMIDAZOL-4-YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1-YL}- N,N-DIETHYLBENZAMIDE; To a solution of INTERMEDIATE 7.1. 5 (18 mg, 0.044 mmol), 4-methyl-lH- imidazole-5-carboxaldehyde (5.8 mg, 0.052 mmol, 1. 2eq) in 1,2-dichloroethane (2 mL) was added sodium triacetoxyborohydride (11.1 mg, 0.052 mmol). The reaction mixture was stirred at room temperature for overnight, then diluted with dichloromethane (5 mL), quenched with saturated aqueous sodium bicarbonate (0.5 mL) and separated. The organic phase was washed with brine (1 x 2 mL), dried (MgSO4) and filtered. To the filtrate ps-scavenger was added, stirred for 2hr and filtered. The filtrate was concentrated and flash chromatography to give compound COMPOUND 12.1. 59 (22 mg, 0.04 mmol, 99%) as colorless oil. lHNMR (500 MHz, CD2C12) : 5 1.10 (br s, 3H), 1.24 (br s, 3H), 1.52 (m, 1H), 1.71 (m, 1H), 1.82 (m, 1H), 1.91 (br s, 2H), 2.05 (m, 1H), 2.15 (m, 1H), 2. 60 (s, 3H), 2.74 (m, 1H), 2.94 (m, 2H), 3.25 (br s, 2H), 3.40 (m, 1H), 3.53 (br s, 2H), 3.55 (br s, 2H), 3.60 (m, 1H), 6.00 (s, 1H), 6.64 (s, 1H), 7 33-7.55 (m, 4H), 8.20 (s, 1H). (+) LRESIMS m/z 503 [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; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

Method 10; A mixture of 4-(4-chloro-phenyl)-4-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- phenyl]-piperidine-l-carboxylic acid tert-butyl ester (200 mg, 0.4 mmol), bis(tri-t- butylphosphine)palladium (0) (6 mg, 3 mol%), 5-bromo-l-methylimidazole (84 mg, 0.5 mmol), potassium carbonate (299 mg, 1.4 mmol), ethanol (1.1 ml), toluene (1.1 ml) methanol (1.6 ml) and water (1.5 ml) was heated in a CEM Explorer microwave to 80 0C for 30 minutes using < 50 watts power. The solvents were removed and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude reaction mixture was purified by SCX ion exchange column chromatography eluting with an ammonia-dichloromethane-methanol EPO mixture to furnish the protected amine. The protecting group was removed by stirring at room temperature in dichloromethane (1 ml) and trifluoroacetic acid (1 ml) for 30 minutes before concentrating and re-concentrating from methanol (x3). The residue was purified by silica column chromatography eluting with a gradient from DMAW90 to DMAW60 furnishing the desired compound in ~90% purity.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2006/136823; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic 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 152628-03-0, category: imidazoles-derivatives

4-Methyl-2-n-propyl-lH-benzimidazole-6-carboxylic acid (50 gms) is suspended in Poly phosphoric acid (300 gms), temperature is raised and maintained for 30 min at 70 – 750C, N-Methyl-o-phenylenediamine dihydrochloride. (45 gms) is added lot wise over 2 hrs and maintained at temperature of 70 – 750C for lhr. The temperature of the reaction mass is raised and maintained for 10 hrs at 130 – 1350C. Mass temperature is cooled to 7O0C, water (600 ml) is added slowly at temperature of 60 – 9O0C. Temperature of the reaction mass is cooled to 3O0C, pH is adjusted to 8.0 – 8.5 with aqueous ammonia solution. EPO Temperature of the reaction mass is raised, maintained at 50- 550C for 1 hr, filter the solid, wet cake is washed with hot water (200 ml) and unload the wet cake. The above wet cake suspended in water (900 ml), temperature is raised and mixed for 1 hr at 50 – 550C. Filtered the solid, washed with hot water (100 ml) and dried the wet cake at temperature of 70 – 750C till constant weight. The above dry material is suspended in methanol (260 ml), and temperature is raised to 45 – 5O0C, charcoal (6.5 gms) is added and mixed for about 30 min. Insolubles are filtered through hyflow bed, washed the bed with hot methanol (60 ml), collect and cooled the filtrate to 250C. Water (160 ml) is added slowly to the filtrate at temperature of 25 – 350C, Mass temperature is raised, maintained for 1 hr at reflux temperature. Reaction mass temperature is cooled, maintained for 2 hrs at 0 – 50C. The solid obtained is filtered, wet cake is washed with methanol (60 ml), the wet cake is dried at temperature of 70 – 750C till becomes constant weight. The dry weight of 4-Methyl-6(l -methyl benzimidazol-2-yl)-2-n-propyl IH- benzimidazole is 54 gms (Yield 77.4%). Water content by KF is 5.85%.

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; MATRIX LABORATORIES LIMITED; WO2007/10558; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem