Month: November 2020

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-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 71759-89-2, 71759-89-2

4-Iodo-1H-imidazole (Compound 25, manufactured by Wako Pure Chemical Industries, Ltd.) (1.9 g, 10 mmol) was dissolved in dichloromethane (40 mL)Triethylamine (2.1 mL, 15 mmol) and trityl chloride (3.4 g, 12 mmol) were added and the mixture was stirred at room temperature (25 C.) for 17 hours under an argon gas atmosphere. After completion of the reaction, water was added and the mixture was extracted twice with dichloromethane. The combined dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluent: chloroform / n-hexane = 1/1 ? chloroform) to obtain compound 26 (4.1 g, 9.3 mmol, yield 93%).

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

Reference:
Patent; NIHON MEDI-PHYSICS COMPANY LIMITED; KYOTO UNIVERSITY; OKUMURA, YUKI; IZAWA, AKIHIRO; AKAMA, KEI; KOBASHI, NOBUYA; ABE, TSUTOMU; SAJI, HIDEO; KIMURA, HIROYUKI; (28 pag.)JP2015/93831; (2015); A;,
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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., 641571-11-1

Example 31[00105] Form B of the free base of 4-methyl-N-[3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-phenyl] -3 -(4-pyridin-3 -yl-pyrimidin-2-ylamino)-benzamide is made according to the following scheme: EPO Eq.)10 [00106] 14.5 g (60.0 mmol) of B6 and 20.8 g (64.8 mmol) of B5 are dissolved in 120 niL tetrahydrofuran absolute at room temperature under inert and water-free conditions. The suspension is cooled to IT 0-5C and 101.0 g (180 mmol) of potassium tert-butoxide solution 20% in tetrahydrofuran were added within 1 hour, maintaining the internal temperature at 0-5C. The reaction mixture is heated gradually to IT 50C within 1 hour and then stirred at this temperature for another 1 hour. The reaction mixture (yellow suspension) is quenched at IT 5O0C by the addition of 50 mL of water. Stirring is stopped, and the two phase system is let to separate. The aqueous (lower) phase is removed. Approximately 1.0 mL of acetic acid is added to the organic phase until a pH of ~10 is reached. Seeding crystals (0.2 g) of form B are added to the organic solution. Solvent (260 mL) is distilled off at 80-100C (external temperature) under normal pressure, and simultaneously 260 mL ethanol 94% is added keeping the volume constant, i.e., solvent exchange from tetrahydrofuran to ethanol. The suspension is cooled to IT 0-5C within 1 hour, and agitation is continued for another 1 hour. Form B of the free base of 4-methyl-N-[3-(4-methyl-imidazol-l-yl)-5-trifluoromethyl- phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide (crystalline solid) is collected by filtration and washed with 150 mL of cold ethanol 94%. The product is then dried at 50C in vacuo.

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; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2007/15870; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 139481-72-4, name is Trityl candesartan, molecular formula is C43H34N6O3, 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. 139481-72-4.

Example 2: Method of Making Cilexetil Trityl Candesartan with a PTC; A suspension of trityl candesartan (2.0 g, 2.93 mmol), cilexetil chloride (1.21 g, 5.86 mmol), potassium carbonate (1.22 g, 8.83 mmol), and tetrabutylammoniumhydrogensulfate (0.2 g) in toluene (20 ml) was stirred at 50C to 55 C for about 8. 5 h. The reaction progress was monitored by TLC. The mixture was poured into water (100 ml) and neutralized with citric acid (solid). The organic layer was separated, washed with water, and extracted with ethyl acetate (20 ml x 3). The combined organic layers were washed with brine (10 ml), dried over sodium sulfate, and evaporated. The residue was triturated with hexane (20 ml) at 20-25C for about 30 min, filtered and dried at 40C and at less than about 30mbar to give white powder (1.68 gr, 67.2%), with 97.90% purity by HPLC.

The synthetic route of Trityl candesartan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/37821; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

614-97-1, A common compound: 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: In a typical reaction procedure, benzimidazole (1mmol), different derivatives of ammonia (1mmol), 0.5 mol% [Ru(bpy)3]Cl2 were taken in a single necked round bottom flask. The reaction mixture was stirred at room temperature under blue light. The completion of the reaction (indicated by disappearance of the starting material and formation of new product, observed by TLC (30:70%) ethyl acetate and hexane. After the product formation 15 ml ethyl acetate and 10 ml water were added. The organic reactants and product were taken out with ethyl acetate and [Ru(bpy)3]Cl2 were dissolved and taken out with water.

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-Methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Siddiqui; Ibad, Farah; Ibad, Afshan; Abdul Waseem, Malik; Watal, Geeta; Tetrahedron Letters; vol. 57; 1; (2016); p. 5 – 10;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, name is 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. 288-32-4

The imidazole was weighed into a round-bottomed flask containing 51% anhydrous tetrahydrofuran and shaken for use.Lithium hydride( 168,221] 11] 1 0 1)Under ice-cooling conditions, was slowly added to a solution containing 51] 11 anhydrous tetrahydrofuran.Flask, shake ready; in the ice bath and nitrogen protection conditions, the imidazole solution slowly dropping into the lithium hydride solution, and then 1-Chloro-3-bromopropane (1 mL, 10 mmol) in tetrahydrofuran was slowly added dropwise to the above mixed solution under a nitrogen atmosphere, and 25 C for 24 h. The reaction was quenched by slow addition of distilled water until a clear layer was formed; and the vacuum was distilled at room temperature to remove tetrahydro-Furan; extraction with carbon dioxide (5 X 5 mL), combining organic layers, and evaporation of carbon dioxide to give intermediate 1. Preparation of the middleThe structure was confirmed by 1Hz NMR, 13C NMR. Said intermediate 1 has the following structure:

Statistics shows that 288-32-4 is playing an increasingly important role. we look forward to future research findings about 1H-Imidazole.

Reference:
Patent; Taizhou University; Ying, Anguo; Chen, Gang; Yang, Jianguo; Hou, Hailiang; Hu, Huanan; (11 pag.)CN105439908; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H5F3N2, 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. 312-73-2.

To a 200 mL eggplant-shaped flask equipped with a magnetic stirrer, 18.7 g (100 mmol) of 2-trifluoromethylbenzimidazole, 16.6 g (120 mmol) of potassium carbonate, 17.0 g (120 mmol) of methyl iodide and 100 mL of acetone were added. The mixture was heated to reflux for 3 hours. After the reaction mixture was cooled, water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 19.7 g of gray crystals. Yield: 98%. 1H-NMR (400 MHz, CDCl3, relative to TMS) delta (ppm): 3.96 (s, 3H), 7.37-7.46 (m, 3H), 7.88 (d, J=6.0 Hz, 1H).

The synthetic route of 2-(Trifluoromethyl)-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; KUMIAI CHEMICAL INDUSTRY CO., LTD.; KAWAZOE, Kentaro; YOSHIOKA, Kotaro; (107 pag.)US2017/197920; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, 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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Imidazole (3)/benzimidazole(5) (10 mmol) was dissolved in 10 ml of DMSO and solid NaOH(15 mmol) was then added it. The resulting pale yellow suspensionwas stirred in air at room temperature for 1.5 h, after which, thealkyl bromides or benzyl chlorides (15 mmol) were added andallowed to react until completion (TLC). Water (50 ml) was thenadded and the products were extracted with ethyl acetate. Combinedorganic layers were washed several times with water, thenwith brine, dried over Na2SO4 and subjected to chromatographicpurification over silica (100-200 mesh) using MeOH: EtOAc 5:95(v/v) as the mobile phase. Compounds 4a-f were isolated as yellowoils whereas, the compounds 7a-e were white solid. Spectroscopic data of the N-alkyl imidazoles are in accord with earlier literatureand thus are not shown here [30].

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:
Article; Chatterjee, Tanmay; Kumar, N. Tanmaya; Das, Samar K.; Polyhedron; vol. 127; (2017); p. 68 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, 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. 934-22-5 name is 6-Aminobenzimidazole, 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.

To the solution of 1H-benzimidazol-5-amine 121 (0.68 g, 5.11 mmol) in acetic acid (20 mL), the Compound 120a (1.06 g, 5.62 mmol) was added and stirred at room temperature for 20 minutes. TMSCN (1 mL) was added dropwise to the reaction mixture and continuously stirred for 2 hours. After reaction completing, the reaction mixture was concentrated under reduced pressure to yield a viscous liquid. The viscous liquid was diluted with ethyl acetate (10 mL) and water. The diluted solution was adjusted to the pH 6-7 with ammonia at an ice-bath. The neutralized solution was extracted with ethyl acetate (20 mL x 4), dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a viscous dark-yellow solid. The solid was dissolved in ethyl acetate (15 mL) and brine (15 mL). The mixture was stirred at room temperature for 2 minutes to form the pale-yellow precipitates. The pale-yellow precipitates was filtered and washed with water. The filtrate was dried over sodium sulfate and concentrated under reduced pressure to obtain the pale- yellow solid. Those pale-yellow solids were combined as the desired product 122a at a yield of 96%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; SHIH, Chuan; NATIONAL HEALTH RESEARCH INSTITUTES; ACADEMIA SINICA; CHEN, Chih-Hao; CHEN, Chiung-Tong; WANG, Hwei-Jiung; HUANG, Kai-Fa; (130 pag.)WO2020/47360; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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. 641571-11-1.

Example 15; Preparation of Nilotinib.3HCl (crude)3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylbenzoyl chloride dihydrochloride of formula (X-Cl).2HCl (105 gms) was added to dichloromethane (1000 ml) and 3-(trifluoromethyl)-5-(4-methyl-1H-imidazol-1-yl)benzenamine of formula I (71 gms) at 25-40 C. The temperature was raised to reflux point and was stirred at this temperature for 10-12 Hours. The reaction mixture was then cooled to 30-20 C. The obtained slurry was filtered and the solid was washed with dichloromethane (200 ml). The wet product was dried at 40-60 C. under reduced pressure.The X-ray powder diffraction of the obtained product is shown in FIG. 3. The X-ray powder diffraction of the obtained product after exposure to 100% humidity for 96% is shown in FIG. 4. Yield: 90-92% Purity: 85-90% Hydrochloride content (by Argentometry titration): 16.8%.

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

7189-69-7, 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. 7189-69-7 name is 1,1′-Sulfonyldiimidazole, 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: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Sulfonyldiimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem