Tag: M.W=200-300

These common heterocyclic compound, 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, 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: 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde

2-Methyl-2-butene (5.0 mL), sodium dihydrogenphosphate dihydrate (1.55 g) and sodium chlorite (3.14 g) were added to a solution containing 4-(1H-imidazol-1-yl)-3-methoxybenzaldehyde (2 g) in water (10 mL) and tert-butanol (30 mL), and the reaction solution was stirred for two hours. The generated solid was collected by filtration to obtain the title compound (745 mg). The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 3.89 (s, 3H), 7.09 (s, 1H), 7.54 (m, 2H), 7.63 (dd, J = 8.0, 1.6 Hz, 1H), 7.69 (d, J = 1.6 Hz, 1H), 8.05 (s, 1H).

The synthetic route of 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2019093; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine 110 g (0.45 moles) of formula (XI) was dissolved in 1 L of chloroform. 4-methyl-3-nitro benzoyl chloride of the formula (IIA) prepared above was added slowly to the reaction mass at 10-15 C. for 60 minutes. Reaction mass was raised to room temperature and maintained for 4 hours. Reaction mass was filtered, washed with chloroform and dried.Yield: 161 g (87%) Purity: 99% (by HPLC) [0059] IR and NMR were consistent with the proposed structure.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Natco Pharma Limited; Kompella, Amala; Bhujanga Rao, Adibhatla Kali Satya; Rachakonda, Sreenivas; Gampa, Venugopala Krishna; Nannapaneni, Venkaiah Chowdary; US2013/210847; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of Nilotinib 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (55 gm), 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzenamine (45 gm), diethylcyanophosphonate (63 ml), triethylamine (78 ml) and N,N-dimethylformamide (1100 ml) were added at room temperature. The contents were heated to 60 C. and maintained for 13 hours at 60 C. The reaction mass was then cooled to room temperature and quenched with sodium bicarbonate solution (8%) and ethyl acetate. Then the layers were separated and ethyl acetate layer washed with sodium chloride solution. The separated ethyl acetate layer was then concentrated to obtain a residual solid. To the residual solid was added water (500 ml) and stirred for 30 minutes at room temperature. The separated solid was filtered and dried to obtain a solid. To the solid was added to teterahydrofuran (900 ml) and stirred for 30 minutes at 50 to 55 C. The teterahydrofuran solvent was distilled off under vacuum to obtain a residual solid. To the residual solid was added ethyl acetate (900 ml) and stirred for 1 hour at room temperature. The solid obtained was collected by filtration and dried to obtain 54 gm of nilotinib. Example 2 Preparation of Nilotinib Hydrochloride Crystalline Form H1 [0048] Nilotinib (3 gm) as obtained in example 1 was suspended in ethanol (120 ml) and then heated to reflux. A solution of hydrochloric acid in ethyl acetate (4 ml) was added to the solution at reflux and stirred for 1 hour at reflux. The ethanol solvent was distilled off under vacuum to obtain a residual mass. To the residual mass was added ethyl acetate (50 ml) and then cooled to room temperature. The reaction mass was stirred for 1 hour at room temperature and filtered. The solid obtained was dried to give 3 gm of nilotinib hydrochloride crystalline form H1.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hetero Research Foundation; Reddy, Bandi Parthasaradhi; Reddy, Kura Rathnakar; Reddy, Dasari Muralidhara; Rao, Thungathurthy Srinivasa; Krishna, Bandi Vamsi; US2013/245052; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13275-42-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13275-42-8 name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: 2-(2-Bromophenyl)benzimidazole (1 mmol), substituted aldehyde (1.2 mmol), NaN3 (1.8 mmol), Cu (10mol%), L-proline (20 mol%), and Cs2CO3 (1 mmol) were added to DMF in a 50 mL round bottom flask, and then the mixture was refluxed at 80 C for 16 h under nitrogen atmosphere. TLC was monitored the reaction till completed, and then the reaction mixture was cooled to room temperature. The mixture was poured into the dichloromethane, washed with brine and water. The organic layer was concentrated with evaporator, and the residue was purified by column chromatography on silica gel to give the target compound (A-4 to A-37).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Bromophenyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Article; Li, Jun-cai; Wang, Ren-xuan; Sun, Yu; Zhu, Jia-kai; Hu, Guan-fang; Wang, Yu-ling; Zhou, Rui; Zhao, Zhong-min; Liu, Ying-qian; Peng, Jing-wen; Yan, Yin-fang; Shang, Xiao-fei; Bioorganic Chemistry; vol. 92; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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: 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

In a 50 mL flask equipped with a thermometer, 1.31 g (5.0 mmol) of 1,3,4,6-tetrakis (hydroxymethyl) glycoluril,Pyridine 3.90 g (50.0 mmol)And 25 mL of N, N-dimethylformamide.To the resulting mixture was added, under ice cooling,After 5.33 g (50.0 mmol) of methacryloyl chloride was added dropwise,And the mixture was stirred overnight at room temperature.After this,100 mL of water was added to the obtained reaction mixture,Extraction operation was carried out with 100 mL of ethyl acetate.The obtained organic layer was concentrated under reduced pressure,The obtained concentrate was purified by silica gel chromatography (ethyl acetate / hexane = 1/1 (volume ratio)),733 mg of 1,3,4,6-tetrakis (methacryloyloxymethyl) glycoluril was obtained as a colorless liquid.Yield 27%.

The synthetic route of 5395-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; KUMANO, TAKESHI; TAKEDA, TAKUMA; MIZOBE, NOBORU; (9 pag.)JP2015/57375; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, 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 39513-26-3, HPLC of Formula: C7H5BrN2O

Sodium hydride (60% in mineral oil, 256 mg, 6 4 mmol) was added to a solution of 5- Bromo-1 3-diotahydro-1 ,3-diotahydro-benzoiotarmdazol-2-one (427 mg, 2 mmol) in DMF (20 mL) at room temperature After 10 min, iodomethane (710 mg, 5 mmol) was added dropwise, and the resulting mixture was stirred at room temperature for overnight (15 hrs) The reaction was quenched with water (100 mL) and extracted with ethyl acetate (125 mL x 3) The combined extracts were washed with water (100 mL x2), saturated aqueous NaCI solution (100 mL), dried with MgSO4 After concentration, a pale yellow solid was obtained (539 mg) without further punfication

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-Bromo-1,3-dihydrobenzoimidazol-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); 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. 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4ClF3N2

17. 5-Trifluoromethyl-2-[(4-methoxy-2-pyridylmethyl)thio]-(1H)-benzimidazole 22.1 g (0.1 mole) of 5-trifluoromethyl-2-chlorobenzimidazole and 15.7 g (0.11 mole) of 4-methoxy-2-thiomethylpyridine in 250 ml of isopropanol are heated under reflux for 10 hours. The solvent is stripped off in vacuo, and 500 ml of ice water are added to the residue. The title compound is filtered off with suction and recrystallized from acetonitrile. M.p. 180-182 C.

According to the analysis of related databases, 86604-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung; US4472409; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 870837-70-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 870837-70-0 name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General synthesis of curcumin analogues 25-34 from corresponding benzaldehyde precursors was carried out by modified literature methods (Scheme 5). The appropriate vanillin derivative (1 equiv) and boric anhydride (0.6 equiv), dissolved in anhydrous DMF in a flask which was thoroughly flushed with nitrogen before use, were stirred at room temperature. Under nitrogen, 2,4-pentanedione (0.6 equiv) and 2,2-dimethoxypropane (1 equiv) or tributyl borate (2 equiv) were added dropwise. The mixture was stirred and heated to a temperature of 70 C under nitrogen. About 30 min later, n-butylamine (0.2 equiv) was added dropwise slowly under nitrogen, and the mixture was allowed to stir at 70 C for 2-4 h. At the end of the reaction, the mixture was hydrolyzed by adding hot (70 C) aqueous 5% acetic acid and stirred until it cooled down. The mother liquor was extracted three times with EtOAc, and the combined organic layers were washed three times, dried over anhydrous Na2SO4, and filtered. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Qin; Zhong, Ying; Yan, Lin-Na; Sun, Xun; Gong, Tao; Zhang, Zhi-Rong; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 1010 – 1014;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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. Computed Properties of C4H4Br2N2

[0304] To a solution of 18-1 (3.6 g, 15 mmol) and K2C03 (4.1 g, 30 mmol) in DMF ( 18 mL) was added iodomethane ( 1 .4 mL, 23 mmol) at 25C. The solution was stirred for 1 5 h. The mixture was poured into water and extracted with EA The combined organic phase was dried over anhydrous Na?S04, and the residue was purified by chromatography on silica gel (EA/hexane) to giv e 18-2 (1 .6 g, 41 %). NMR (400 MHz, CDC13): delta 3.52 (s. 3H). 2.21 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 219814-29-6, its application will become more common.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 150058-27-8, 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. 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

60 g of 2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester and 500 ml of ethanol were added to the clean reaction flask, Stirred at room temperature for 10 minutes, 75.5 g of potassium carbonate was added, 60.3g 3-(4′-(bromomethyl)-[1,1′-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one , and 4.8 g of tetrabutylammonium bromide, heated to reflux 10h, the ethanol was evaporated to dryness under reduced pressure, and the mixture was stirred for half an hour in 1800 ml of water, 120ml water washing, filter to dry, solid with 400ml ethanol temperature reflux solution dissolved, cooling to 0-5 , 2 hours of crystallization temperature.Filtered, washed with 20 ml of ethanol, suction filtered to dryness, in 50 to 60 vacuum drying, 2-ethoxy-1-((2′-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)benzimidazole-7-carboxylic acid methyl ester was obtained 66.8 g, yield: 78.0percent, purity: 98.9percent)

The synthetic route of Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chongqing Langtian Pharmacy Co., Ltd.; Meng, Wenxue; Long, Daobing; Sun, Wenjing; (11 pag.)CN105669495; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem