Category: imidazoles-derivatives

1003-21-0, name is 5-Bromo-1-methyl-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. HPLC of Formula: C4H5BrN2

5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol) followed by THF (537 mL) was added to a 3 L four necked flask equipped with an overhead stirrer, nitrogen bubbler and thermocouple. To this room temperature solution was added isopropyl magnesium chloride / lithium chloride complex (246.8 mL, 320.8 mmol, 1.3 M in THF) (addition temperature maintained at 16.6-25 [deg.] C) to give a lean pumice suspension and stir the reaction for 60 min And then cooled to 5.3 in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6- (trifluoromethyl) nicotinamide (53.66 g, 229.1 mmol, intermediate 4: step b) in THF (268 mL) 5.3 to 5.6 & lt; 0 & gt; C) to give an orange mixture. After the addition, the reaction was allowed to warm to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C with an ice bath, carefully quenched with a 2N HCl aqueous solution at pH = 7, and the quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), the phases were separated and the organic layer was washed with brine (2 x 200 mL), dried over sodium sulfate, filtered and the solvent removed. After addition of hot ether, filtration yielded the title compound as a solid.

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

Reference:
Patent; Janssen Pharmaceutica, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (2016); A;,
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 5805-57-2 as follows. Product Details of 5805-57-2

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

Example 1; Synthesis of compound of formula (Ia); To a 1 -L flask, equipped with a mechanical stirrer, temperature sensor, reflux condenser, addition funnel and nitrogen inlet-outlet under a nitrogen atmosphere at 23C is charged with compounds (lie) (16 g), (IVa) (12 g) and THF (300 mL). The mixture is stirred for 15 minutes at 23C and cooled to -2O0C to -15C. A solution of 1 M potassium f-butoxide in THF (275 mL) is added at -2O0C to -100C. After the addition, the mixture is warmed to 18-23C. When the reaction is complete according to HPLC, the mixture is cooled to 5C. A solution of 15% aqueous sodium chloride (500 mL) is added to the mixture, maintaining temperature below 15C. Product is extracted into isopropyl acetate (500 mL) and washed in sequence with 15% aqueous sodium chloride solution (500 mL) and water (500 mL). The organic phase is distilled under atmospheric pressure at an internal temperature of 75-85C until the residual volume is about 200 mL. The resulting suspension is cooled to 70 +/- 5C and charged with ethanol (250 mL) and water (30 mL). The mixture is heated to reflux (780C) for 1 hour and then cooled to -1O0C to -15C. The suspension is stirred for an EPO additional 30 minutes at -1O0C to -15C. Any solid is collected by filtration, rinsed with cold (50C) ethanol (85 ml_) and dried under vacuum (10-20 torr) at 55-6O0C with a nitrogen bleed (8-16 hours) to obtain AMN107 (17.4 g, 67% yield) as a white solid.1H NMR 300 MHz, DMSOd6), delta 10.5 (s, 1 H), 9.15 (s, 1 H), 9.05 (S, 1 H), 8.60 (s, 1 H), 8.45 (d, 1 H), 8.35 (d, 1 H), 8.22 (d, 2H), 8.10 (d, 2H)1 7.65 (m, 2H), 7.45 (m, 4H), 2.25 (s, 3H), 2.05 (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 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2006/135641; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-26-8, The chemical industry reduces the impact on the environment during synthesis 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

COMPOUND 12.1. 32: 4-(f6. 7-DIMETHOXY-2-[(4-METHYL-lH-IMIDAZOL-5- YL) METHYL]-1, 2, 3, 4-TETRAHYDROISOOUINOLIN-1-YLMETHYL)-N,- DIETHYLBENZAMIDE; INTERMEDIATE 5.1. 5 (25 mg, 0.05 mmol) and 1-methyl-4-imidazolecarbaldehyde (12 mg, 0.10 mmol) were dissolved in DCE (5 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (33 mg, 0.16 mmol) was added and the mixture was stirred for 18 h at room temperature. Resin-bound tosylhydrazine (100 mg, 1.5 mmol/g) was added and the mixture was agitated for another 2 h. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman IPS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by preparative LCMS to yield the desired product (10 mg, 0.02, 39%). 1H NMR (500 MHz, CDC13): 1.14, 1.28 (2 brs, 6H), 2.17 (s, 3H), 3.10- 3.60, 3.80 (2 m, 10H), 4.35 (brs, 2H), 4.41 (s, 1H), 6.14, 6.59 (2 s, 2H), 7.29 (m, 4H), 8.50 (brs, 1H). (+) LRESIMS m/z 369 (100), 463 (35).

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, 1-Methyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); 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. 1072-63-5, name is 1-Vinyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2

With reference to FIG. 4, 0.14 mmloe of 1-vinylimidazole, being the imidazolium liquid monomer, and 50 ml of toluene are mixed to obtain a mixture, followed by sequentially dropping 0.16 mmole of 2-bromoethanol into the mixture to trigger off an alkylation of the 1-vinylimidazole and the 2-bromoethanol. Then, a solution with two phase of layering is obtained after three days of reaction, wherein the lower layer of the solution is further isolated and repeatedly washed by toluene and ether, followed by being condensed and dried in vacuo for 1 hour, to obtain 1-(2-hydroxyl-ethyl)-3-vinylimidazolium bromide (also known as HEVIMB).

The synthetic route of 1072-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HORNG, Shiey-Shiun; US2013/274485; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 56248-10-3, name is 5-Phenyl-1H-imidazole-2-carbaldehyde, molecular formula is C10H8N2O, 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: 56248-10-3

General procedure: To a stirred solution of compound 3 (100mg, 0.40 mmol) in ethanol was added corresponding benzohydrazides (4a-m) (1.0 mmol) and refluxed for 1 h. The reaction mass was washed with pet ether, filtered and dried undervacuum to obtain the pure hydrazone compounds. Yields ofthe products varied between 78 and 88 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 56248-10-3, its application will become more common.

Reference:
Article; Prasanna, V. Laxmi; Narender; Asian Journal of Chemistry; vol. 27; 10; (2015); p. 3605 – 3608;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1072-62-4, name is 2-Ethyl-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. Formula: C5H8N2

General procedure: To a solution of 1 (0.02 mmol) in H2O/MeCN (v/v=2/1, 4 mL) was added 1H-imidazole (1.0 mmol) and arylboronic acid (2 mmol)under O2 atmosphere. The mixture was stirred at 60 C for 24 h. After cooling to ambient temperature, the mixture was partitioned between water and CH2Cl2. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel.

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xue, Jiang-Yan; Li, Jun-Chi; Li, Hong-Xi; Li, Hai-Yan; Lang, Jian-Ping; Tetrahedron; vol. 72; 44; (2016); p. 7014 – 7020;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, Computed Properties of C19H13BrN2

(4-7) Synthesis of Compound (4); Into a 300 ml three-necked flask, 1.1 g (2.1 mmole) of Intermediate 14, 1.6 g (4.6 mmole) of 2-(4-bromophenyl)-1-phenylbenzimidazole, 0.10 g (0.09 mmole) of tetrakis(triphenylphosphine)palladium(0), 20 ml of 1,2-dimethoxyethane and 6.5 ml (13 mmole) of a 2 M aqueous solution of sodium carbonate were placed under the stream of argon, and the resultant mixture was heated under the refluxing condition for 8 hours. When the reaction was completed, the organic layer was washed with water and dried with magnesium sulfate, and the solvent was removed by distillation using a rotary evaporator. The obtained crude crystals were washed with 50 ml of toluene and 100 ml of methanol, and 1.6 g of a light yellow powder substance was obtained. The obtained substance was identified to be Compound (4) by the measurement of the field desorption mass spectrum (FD-MS) (the yield: 78percent).

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, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; US8058450; (2011); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 827320-59-2, name is 1-butylsulfonic-3-methylimidazolium hydrogensulfate, 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 827320-59-2, Recommanded Product: 827320-59-2

Weigh the compound obtained in the second step1-sulfobutyl-3-methylimidazole bisulfate ionic liquid (5.06 g, 16.0 mmol)Placed in the reactor;The aqueous hydroxylamine solution 2 obtained in the first step was measured2.9 ml (32.0 mmol as hydroxylamine)Slowly added dropwise to the above ionic liquid,Low temperature (? 0 ) stirring 2h,A colorless transparent reaction liquid;The reaction solution was subjected to rotary evaporation at 70 C,A white solid product was obtained1-sulfobutyl-3-methylimidazole bisulfate ionic liquid-type hydroxylamine salt,The ionic liquid-type hydroxylamine salt was weighed and dried to weigh 4.25 g,The yield was 69.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-butylsulfonic-3-methylimidazolium hydrogensulfate, and friends who are interested can also refer to it.

Reference:
Patent; Hebei University of Technology; Wang, Yanji; Li, Zhihui; Qi, Xudong; Zhang, Dongsheng; Xu, Yuanyuan; Yang, Quisheng; Zhao, Xinqiang; (7 pag.)CN104086487; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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. SDS of cas: 32673-41-9

A mixture of 1,2,3,4-tetrahydro-quinoline (Intermediate F1) (Commercially available from Aldrich) (1.62 mL, 12.6 mmol) and 4-hydroxymethyl-imidazole hydrochloride salt (commercially available from Aldrich) (Intermediate F2) (0.70 g, 5.1 mmol) and sodium carbonate (1.6 g, 15.1 mmol) in water (20 mL) and dioxane (10 mL) were heated at reflux for 24 h. The mixture was cooled to rt and extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and freed of solvent. The resultant oil was purified by chromatography on silica gel with 5% NH3-MeOH: dichloromethane to give 1-(1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3) as a solid, 0.54 g (50%). 1-(1H-Imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3)was subjected to the appropriate process steps in Method A to produce 4-(3,4-dihydro-2H-quinolin-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 11). 1H NMR (300 MHz, DMSO-d6): delta12.0 (s, 1H), 11.8 (s, 1H), 6.93 (t, J=6.9 Hz, 1H), 6.87 (d, J=7.2 Hz, 1H), 6.66-6.63 (m, 1H), 6.63 (s, 1H), 6.50 (t, J=6.9 Hz, 1H), 4.18 (s, 2H), 3.28 (t, J=6.3 Hz, 2H), 2.67 (t, J=6.3 Hz, 2H), 1.90-1.84 (m, 2H).

The synthetic route of 4-Imidazolemethanol hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2006/69143; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem