Author: Jessica.F

These common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-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. COA of Formula: C4H5BrN2

The 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid used in the method described above was prepared as follows: (i) To a stirred solution of 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate (0.200 g, 1.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 2-bromo-1-methyl-1 H-imidazole (0.146 ml, 1.500 mmol) in 1 ,4-dioxane (8 ml) was added potassium phosphate (1.062 g, 5.00 mmol), copper(l) iodide (0.190 g, 1.000 mmol) and trans-N,N-dimethylcyclohexane-1 ,2- diamine (0.155 ml, 1.000 mmol) and the mixture heated at reflux under argon overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The solid was filtered off, washed with dichloromethane and the filtrate reduced under vacuum. The residue was re-dissolved in dichloromethane and washed with 0.880 ammonia solution (x2), water then brine and passed through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by Flashmaster automated silica gel chromatography eluting with 0-10% methanol in dichloromethane to give 1 ,1-dimethylethyl 3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylate (145 mg, 37.8 % yield). LC/MS[M+H]+ = 281.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 15965-31-8, name is 5-Chloro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

A stirred suspension of 4-chloro-lH-imidazole (9.75 mmol, 1.0 g) , 2-chloro-5-nitropyridine (9.75 mmol, 1.54 g) and potassium carbonate (11.70 mmol, 1.61 g) in DMF (10 mL) was heated at 80 C for 3 hours. The mixture was cooled to room temperature and water was added. The resulting precipitate was filtered, washed with water and dried to give crude 6- ( 4-chloroimidazol-l-yl ) -3- nitropyridine (1.94 g, 89%).

The synthetic route of 15965-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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 suspension of 0.351 g of imidazole-2-carboxylic acid (3.13 mmol) in 15 ml DMF were added 0.508 g of CDI (3.13 mmol) and 0.43 ml triethylamine (3.13 mmol), and the mixture stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (2.4 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and trying 0.42 g 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (57%) were obtained as a yellow solid; M.p.: 227-228 C.

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

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57667-50-2, 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. 57667-50-2, name is 1-Propyl-1H-benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

1 ,3-bis(1 -Propyl-1 H-benzo[d]imidazol-2-yl)urea (1 9a) and 1 0-propyl-3-(1 -propyl-1 H-benzo[d]-imidazol2-yl)benzo[4,5]imidazo[1,2-a][1,3,5]triazine-2,4(3H,1OH)-dione (9b) were obtained in 8% (16.0 mg,0.045 mmol) and 12% (0.027 g, 0.067 mmol) yield respectively via a reaction of 1-propyl-1H- benzo[d]imidazol-2-amine (20a) (0.200 g, 1.141 mmol), 4-nitrophenylchloroformate (0.127 g, 0.628 mmol) and DIPEA (0.258 mL, 1.484 mmol) in CH2CI2 (4.0 mL) at room temperature. Reaction time 16h. 1,3-bis(1-Propyl-1H-benzo[d]imidazol-2-yl)urea (19a) White solid ; m.p. 178 o 1H-NMR (400 MHz, CDCI3): : 7.30-7.29(m, 2H), 7.13-7.09(m, 6H), 4.02(t, 4H, J= 7.20 Hz), 1.78(d, 4H, J= 7.60 Hz),0.88 (t, 6H, J = 7.60 Hz). 1 0-propyl-3-(1 -propyl-1 H-benzo[d]imidazol-2-yl)benzo[4,5]imidazo[1 2- a][1 ,3,5]triazine-2,4(3H,1OH)-dione (9b). Colorless solid; m.p. 222 C. 1H-NMR (400 MHz, DMSO-d6):: 8.01 (d, 1H, J = 7.60 Hz), 7.75 (d, 1H, J = 8.00 Hz), 7.71 -7.67 (m, 2H), 7.54-7.49 (t, 2H, J = 8.00 Hz), 7.41-7.28(m, 3H), 4.21-4.04(m, 4H), 1.91-1.81 (m, 2H), 1.79-1.69(m, 2H), 1.00(t, 3H, J= 7.20 Hz), 0.87 (t, 3H, J = 7.20 Hz).

The chemical industry reduces the impact on the environment during synthesis 1-Propyl-1H-benzo[d]imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; MAES, Bert; WYBON, Clarence; CHEN, Chen; BHEETER, Charles Beromeo; SERGUEEV, Serguei; (88 pag.)WO2017/46133; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C5H6N2O2

(1) To a solution of methyl 4-imidazole carboxylate (a-1) (1.2 g, 9.5 mmol) and (4-fluorophenyl)methanol (h-1) (1.2 mL, 11 mmol) in THF (12 mL), PPh3 (3.0 g, 11 mmol) and DIAD (2.2 mL, 11 mmol) were added and the resulting mixture was stirred overnight at room temperature. The solvent was distilled off under reduced pressure and ethyl acetate and n-hexane were added; the resulting solids were recovered by filtration. The solvents in the filtrate were distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:1050:50) to give methyl 1-(4-fluorobenzyl)-1H-imidazole-5-carboxylate (h-2) (amount, 1.6 g; yield, 73%).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; IKEGAMI, Satoru; WATANABE, Atsushi; HIRANO, Kimio; OHYAMA, Tadashi; (56 pag.)US2016/130232; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile

3- Methoxy-4-(4-methyl-1 /-/-imidazol-1-yl)benzonitrile (46.9 g, 0.22 mol), in methanol (176 ml_) and water (88 ml_), were treated with potassium hydroxide (85%, 16.5 g, 0.25 mol) and the resulting solution was refluxed for 72 hours. The solution was concentrated in vacuo to approximately 100 ml_, and the resulting solid was removed by filtration. Water (40 ml_) was added to the filtrate, which was then acidified to pH 5 by addition of small portions of 30% aqueous hydrochloric acid (approximately 40 ml_). The resulting thick suspension was heated to reflux for 5 minutes and left to cool overnight. The mixture was filtered, and the white solid was washed with water (3 x 20 ml_) and dried in vacuo to afford the title compound as a white powder. Yield: 53.76 g, 0.231 mmol, quantitative. LCMS m/z 233.1 (M+1 ). 1H NMR (300 MHz, CD3OD) 5 2.36 (d, J=1.0 Hz, 3H), 3.97 (s, 3H), 7.43 (m, 1H), 7.56 (d, J=8.2 Hz, 1 H), 7.76 (dd, J=8.1 , 1.7 Hz, 1 H), 7.84 (d, J=1.6 Hz, 1 H), 8.66 (d, J=1.5 Hz, 1 H).

The synthetic route of 1243204-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 57090-88-7, A common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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.

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, These common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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.

A mixture of glycoluril (500 g, 3.51 mol) and paraformaldehyde (105 g, 3.51 mol) in HCl (8 M, 70 mL) was heated at 50 C for 48 h. The reaction mixture was cooled and filtered. The solid was washed with water (500 mL) and then recrystallized with TFA (1.5 L) to yield Glycoluril Dimer as a white solid (334 g, 62 %).

Statistics shows that Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione is playing an increasingly important role. we look forward to future research findings about 496-46-8.

Reference:
Patent; UNIVERSITY OF MARYLAND, COLLEGE PARK; THE GENERAL HOSPITAL CORPORATION; ISAACS, Lyle, David; EIKERMANN, Matthias; CUSIN, Cristina; COTTEN, Joseph; (128 pag.)WO2016/61571; (2016); 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. 914306-50-6, name is 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 914306-50-6

(Step 3) Into a three-head flask, there were put 2.8 g of the intermediate body C obtained in Step 2, 1.6 g of an intermediate body D, and 50 ml of ethylene glycol, and this mixture was heated and stirred for 7 hours at 150 C. under a nitrogen atmosphere. Precipitated crystals were obtained by filtration, and the crystals obtained by the filtration were washed by methanol, and thereafter, were separated and purified by silica gel chromatography, whereby 0.7 g of the DP-1 was obtained. A structure of the compound example DP-1 was confirmed by MASS spectrum and 1H-NMR. MASS spectrum (ESI): m/z=1179 [M+] 1H-NMR (CD2CI2, 400 MHz) delta: 7.71 (2H, d, J=28.3 Hz), 7.42 (1H, t, J=28.3 Hz), 7.33-7.57 (6H, m), 7.34 (4H, t, J-33.2 Hz), 6.96 (2H, 5), 6.81-6.86 (6H, m), 6.69 (2H, d, J=33.2 Hz), 6.56-6.60 (2H, m), 6.44 (1H, t, J=23.4 Hz), 6.38 (2H, d, J=17.6 Hz), 6.32 (1H, d, J=23.4 Hz), 6.16 (2H, d, J=44.9 Hz), 2.65-2.80 (3H, m, CH of iso-Pr), 2.29-2.41 (3H, m, CH of iso-Pr), 1.26 (3H, d, J=26.3 Hz, CH3 of iso-Pr), 1.21 (6H, d, J=20.5 Hz, CH3 of iso-Pr), 0.92-1.08 (m, 27H, CH3 of iso-Pr)

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; KONICA MINOLTA ADVANCED LAYERS, INC.; OTSU, Shinya; ONO, Kaori; KATOH, Eisaku; US2013/200340; (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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 137049-00-4

Intermediate example 1-84 (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl l-methyl-lH-imidazole-4- sulfonateTo a solution of (35)-3-(dibenzylamino)chroman-5-ol (300 mg, 0.87 mmol, described in WO9914212A1) in acetonitrile (10 mL) was triethylamine (0.363 mL, 2.61 mmol) and 1- methyl-leta-imidazole-4-sulfonyl chloride (173 mg, 0.96 mmol) added and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was concentrated in vacuo and purified by column chromatography using a gradient of ethyl acetate in heptane to yield 375 mg (88 %); 1H NMR (400 MHz, DMSO-J6) delta ppm 8.06 (d, 1 H), 7.93 (d, 1 H), 7.30 – 7.42 (m, 8 H), 7.18 – 7.27 (m, 2 H), 7.06 (t, 1 H), 6.69 (dd, 1 H), 6.62 (dd, 1 H), 4.17 – 4.31 (m, 1 H), 3.97 (t, 1 H), 3.61 – 3.73 (m, 7 H), 2.84 – 2.99 (m, 2 H), 2.63 – 2.75 (m, 1 H); MS (ESI) m/z 490 [M+H+].

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 137049-00-4.

Reference:
Patent; ASTRAZENECA AB; WO2008/130319; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem