Category: imidazoles-derivatives

These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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. Recommanded Product: 39021-62-0

3-Methyl-3H-imidazole-4- carbaldehyde (10) (4.0 g, 15 mmol) was suspended in THF (10 mL), and the resulting solution cooled to 0°C. Lithium aluminum hydride (300 mg, 32.0 mmol) was added portion wise over 10 minutes, and the resulting suspension stirred for a further 10 minutes. Excess hydride was quenched by the addition of solid Na2SO4-IOH2O (~1 g) in large portions with vigorous stirring. Additional THF was added as needed to prevent solidification of the resulting slurry. The resulting suspension was stirred for a further hour, and then filtered to remove the sulfate salts, and the solvent was removed under reduced pressure to provide the title alcohol (1.3 g, 80percent). 1H NMR (400 MHz, ^-MeOH): delta 7.57 (s, IH), 6.89 (s, IH), 4.58 (s, 2H), 372 (s, 3H). 13C NMR (100 MHz, ^-MeOH): delta 140.1, 132.7, 128.1, 31.9, 31.0.

The synthetic route of 1-Methyl-1H-imidazole-5-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; UNIVERSITY OF SOUTH FLORIDA; UNIVERSITY OF WASHINGTON; SEBTI, Said; WO2006/102159; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 13739-48-5, name is 2-Methyl-4-phenyl-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 13739-48-5, Computed Properties of C10H10N2

5.86 3-{4-[4-(2-METHYL-4-PHENYL-IMIDAZOL-1-YLMETHYL)-BENZYLOXY]-1-OXO-1,3-DIHYDRO-ISOINDOL-2-YL}-PIPERIDINE-2,6-DIONE To the stirred solution of 2-methyl-4-phenyl-1H-imidazole (157 mg, 0.99 mmol) in Acetonitrile (15 mL) was added 3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (400 mg, 0.9 mmol) and DIPEA (0.24 ml, 1.35 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 days before the reaction mixture was diluted by EtOAc (40 mL) and NaHCO3 (aq, sat., 20 mL). The mixture was extracted. Some solid was formed and the mixture was filtered. And the solid was dissolved in DCM (20 mL) and MeOH (5 mL). All organic layers were combined and dried by MgSO4 and concentrated. The residue was purified by ISCO to give 3-{4-[4-(2-Methyl-4-phenyl-imidazol-1-ylmethyl)-benzyloxy]-1-oxo-1,3-dihydro-isoindol-2-yl}-piperidine-2,6-dione as a white solid (310 mg, 66% yield). HPLC: Waters Symmetry C-18, 3.9*150 mm, 5 mum, 1 mL/min, 240 nm, 25/75, (CH3CN/0.1% H3PO4), 5.26 min (99.6%); mp: 270-272 C.; 1H NMR (DMSO-d6) delta 1.91-2.03 (m, 1H, CHH), 2.30 (s, 3H, CH3), 2.43 (dd, J=4.3, 13.0 Hz, 1H, CHH), 2.53-2.63 (m, 1H, CHH), 2.82-2.97 (m, 1H, CHH), 4.23 (d, J=17.6 Hz, 1H, CHH), 4.39 (d, J=17.6 Hz, 1H, CHH), 5.04-5.16 (m, 1H, CHH), 5.18 (s, 2H, CH2), 5.23 (s, 2H, CH2), 7.10-7.20 (m, 1H, Ar), 7.20-7.26 (m, J=8.1 Hz, 2H, Ar), 7.26-7.36 (m, 4H, Ar), 7.42-7.54 (m, 314, Ar), 7.62 (s, 1H, NH), 7.64-7.75 (m, 2H, Ar), 10.96 (s, 1H, NH); 13C NMR (DMSO-d6) delta 12.76, 22.31, 31.16, 45.04, 48.59, 51.55, 69.17, 114.93, 115.25, 116.49, 123.92, 125.88, 127.15, 128.14, 128.36, 129.78, 129.95, 133.30, 134.58, 135.98, 137.15, 138.50, 144.57, 153.39, 167.97, 170.93, 172.80; LCMS MH=521; Anal. Calcd for C31H28N4O4+0.3 H2O: C, 70.79; H, 5.48; N, 10.65; Found: C, 70.68; H, 5.21; N, 10.52. The regio isomeric structure was confirmed by ROESY.

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; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); 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. 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7BrN2O2

250 mg (1.14 mmol) of the bromide (ABCR), 400 mg (1.14 mmol) of 2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 39 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) were initially charged in a mixture of degassed acetonitrile (4 ml) and degassed sodium carbonate solution (1M, 5 ml), and the mixture was stirred at 72 C. for 14 h. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure, and the residue was taken up in dichloromethane. The organic phase was washed with water, dried over magnesium sulphate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography purification using a cyclohexane/acetone gradient as mobile phase. (0569) log P (acidic/neutral): 3.09/3.19; MH+: 363; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 2.46 (s, 3H), 3.71 (s, 3H), 3.83 (s, 3H), 3.99 (q, 2H), 7.42 (d, 1H), 7.75 (d, 1H), 7.81 (s, 1H).

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; Bayer CropScience Aktiengesellschaft; JANSEN, Johannes-Rudolf; HEIL, Markus; FISCHER, Reiner; WILCKE, David; WILLOT, Matthieu; ILG, Kerstin; EILMUS, Sascha; LOeSEL, Peter; ANDERSCH, Wolfram; (69 pag.)US2019/47982; (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. 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H5N3

Example 1 Synthesis of 2-(1-imidazolyl)-2-(4-isobutyl-1,3-dithiolan-2-ylidene)acetonitrile (Compound Nos. 8 and 9) To a mixed solution of 0.55 g (0.005 mole) of 1-cyanomethylimidazole, 0.4 g (0.005 mole) of carbon disulfide and 10 ml of dimethyl sulfoxide was added 0.8 g (0.014 mole) of potassium hydroxide powder with stirring, and the reaction was carried out at room temperature for 1 hour. Then, 1.5 g (0.006 mole) of 1,2-dibromo-4-methylpentane was added dropwise with stirring, and the resulting solution was subjected to reaction for 2 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, after which the resulting mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with water and dried. The solvent was distilled off and the residue was purified by silica gel chromatography to obtain 0.45 g of the Z isomer and 0.3 g of the E isomer individually in the form of colorless crystals. The Z isomer (Compound No. 8): melting point 73.3C, yield 34%. The E isomer (Compound No. 9): melting point 118.1C, yield 23%.

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; NIHON NOHYAKU CO., LTD.; EP218736; (1987); 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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 26663-77-4

A solution of methyl lH-benzo[d]imidazole-6-carboxylate (9.5 g, 53.9 mmol) in THF (100 mL) had NaH (2.59 g, 64.7 mmol) added at 0C. After stirring for 30 min, CH3I (13.23 g, 93.2 mmol) was added and the mixture was stirred at room temperature for lh. The reaction was then quenched by addition of water and extracted with DCM (3×100 mL). The combined organic layers were dried over Na2S04 and concentrated to give a mixture of two isomeric products methyl 1 -methyl- lH-benzo[d]imidazole-6-carboxylate and methyl 1- methyl-lH-benzo[d]imidazole-5-carboxylate (8.0 g, Yield 78%). LCMS (m/z): 191.06 (M+l). This crude mixture was used directly in the next step.

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 26663-77-4.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100695; (2014); 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

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

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

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

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