Category: imidazoles-derivatives

Application of 39070-14-9, These common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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.

Phenstatin (0.500 g, 1.57 mmol), (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (0.296 g, 1.89 mmol), and DIAD (0.40 mL, 2.04 mmol) were dissolved in CH2Cl2. Triphenylphosphine (0.825 g, 3.14 mmol) was added to the mixture, and the reaction mixture was stirred for 24 h. The reaction mixture was then evaporated under reduced pressure. Flash chromatography of the crude product using a prepacked 100 g silica column [eluents: solvent A: EtOAc; solvent B: hexanes; gradient, 17%A/83%B over 1.19 min (1 CV), 17%A/83%B 100%A/0%B over 8.33 min (7 CV), 100%A / 0%B over 5.95 min (5 CV); flow rate 100 mL/min; monitored at 254 and 280 nm] yielded (4-methoxy-3-((1-methyl-2-nitro-1H-imidazol-5-yl)methoxy)phenyl)(3,4,5-trimethoxyphenyl)methanone (31) as a pale yellow-white solid (0.346 g, 0.757 mmol, 48%) [0.284 g, 0.621 mmol, 39%, corrected for EtOAc].1H NMR (600 MHz, CDCl3) delta 7.62 (1H, d, J = 1.7 Hz), 7.52 (1H, dd, J = 8.3, 1.7 Hz), 7.24 (1H, s), 7.04 (2H, s), 6.97 (1H, d, J = 8.4 Hz), 5.18 (2H, s), 4.16 (3H, s), 3.97 (3H, s), 3.96 (3H, s), 3.91 (6H, s).13C NMR (151 MHz, CDCl3) delta 194.16, 153.97, 152.91, 146.74, 141.88, 132.92, 132.30, 130.43, 129.31, 127.00, 116.43, 110.61, 107.52, 99.98, 61.24, 61.01, 56.39, 56.05, 34.54.HRMS [M+Na]+: 480.1376 (calcd for [C22H23N3NaO8]+,480.1377).HPLC retention time (Method B): 4.66 min [100% at 254 nm].

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Winn, Blake A.; Shi, Zhe; Carlson, Graham J.; Wang, Yifan; Nguyen, Benson L.; Kelly, Evan M.; Ross, R. David; Hamel, Ernest; Chaplin, David J.; Trawick, Mary L.; Pinney, Kevin G.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 636 – 641;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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 comprising compound 158B (350 mg; 0.88 mmol) and 1-trityl-1H-imidazole-4-carboxaldehyde (352 mg; 1.00 mmol) dissolved in 1,2-dichloroethane (DCE) (4.5 ml) in the presence of acetic acid (0.3 ml) is stirred for 5 minutes at room temperature and sodium triacetoxyborohydride (233 mg; 1.10 mmol) is then added. The mixture is stirred overnight at room temperature and is then diluted with ethyl acetate and washed successively with saturated NaHCO3 solution, with water, and with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated. This crude reaction, product is then purified by flash chromatography (gradient: 4/1 and then 2/1 CH2Cl2/acetone) to give the desired product (304 mg; 48%). [0268] 1H NMR, DMSO-d6 (ppm): 1.88 (m, 2H); 2.00 (s, 3H); 2.33 (m, 2H); 3.63 (s, 3H); 4.03 (d, 2H, 5.2 Hz); 4.50 (m, 1H); 5.45 (t, 1H, 5.6 Hz); 6.55 (s, 1H); 6.70 (s, 1H); 6.76 (d, 1H, 8.7 Hz); 7.01 (m, 6H); 7.21 (d, 1H, 8.7 Hz); 7.25 (s, 1H); 7.31-7.41 (m, 13H); 7.55 (d, 1H, 7.4 Hz); 7.73 (d, 3H, 9.4 Hz); 11.35 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Trityl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Perez, Michel; Lamothe, Marie; Hill, Bridget; Etievant, Chantal; US2004/204417; (2004); 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C5H6N2O

COMPOUND 12. 1.21 : N, N-DIETHYL-4-E1, 2, 3, 4-TETRAHYDRO-6-METHOXY-2- [ 4-METHYL-lH-IMIDAZOL-5-YL) METHYLI-1-ISOOUINOLINYLI- BENZAMIDE; INTERMEDIATE 5.1. 8 (1.1 g, 3.25 mmol) was dissolved in 1,2-dichloroethane (70 mL), 4-methyl-imidazole-5-carboxaldehyde (716 mg, 6.5 mmol) was added and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (2. 1 g, 9.8 mmol) was added and the reaction mixture stirred for a further 16 h. MeOH (5 mL) was added and the reaction mixture concentrated to dryness. The resulting residue was partitioned between EtOAc (50 mL) and NaOH (1N, 30 mL), the aqueous phase washed with EtOAc (2 x 50 mL), dried (MgS04), filtered and concentrated to dryness. The resulting residue was purified by flash chromatography on silica gel (10: 1, DCM: MeOH) to afford COMPOUND 12.1. 21 (736 mg, 54%) as a colourless oil. 1H NMR (500 MHz, CDC) : 8 1. 13,1. 24 (br s, 6H), 2.09 (s), 2.53 (td, J4, 13 Hz, ), 2.76 (br d, J 17 Hz, 1H, ), 2.98 (m, 1H), 3.09 (m, 1H), 3. 28 (br s, 2H), 3.55 (br s, 2H), 3.33 (d, J2 Hz, 1H), 3.60 (d, J2Hz, 1H), 3.76 (s, 3H), 4.56 (s, 1H), 6.58 (s, 1H), 6.64 (br s, 1H), 7.29-7. 30 (m, 5H), 8.30 (s, 1H). 13C NMR (125 MHz, CDC13) : 5 11.2, 13.1, 14.5, 29.2, 39.6, 43.7, 47.0, 49.6, 55.4, 68.0, 112.6, 113.0, 126.5, 127.0, 129.9, 130.0, 130.1, 133.2, 136.1, 136.2, 145.9, 158.1, 171.6. (+) LRESIMS m/z 433 [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

Adding a certain compound to certain chemical reactions, such as: 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, 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 38993-84-9, Computed Properties of C5H8N2O

Thionyl chloride (3.88mL, 53.5mmol) was added dropwise to 3-methyl-3H-imidazol-4- yl)-methanol (o.3g, 2.68mmol). The reaction was sonicated briefly, treated with DMF (1 drop) and allowed to stir at ambident temperature for 1 h. The volatiles were removed and the residue treated with diethyl ether. The diethyl ether was decanted and the procedure repeated 3 times. The semi-solid residue was treated with dimethylamine in THF (6.69mL, 13.38mmol) followed DMF (1 mL). The reaction was heated in a CEM microwave reactor at 8O0C for 30 minutes, treated with acetic acid (1 ml_) and purified by SCX cartridge to give the title compound (0.18g, 1.22mmol). LC-MS (method 1): R, 2.9 min, m/z 140 [MH]+.

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-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2008/23157; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 50995-95-4, name is 2-Propylimidazole, 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 50995-95-4, Application In Synthesis of 2-Propylimidazole

Example 30 Methyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionate (1.50 g) and 2-propylimidazole (0.66 g) were dissolved in N,N-dimethylformamide (10 ml), and sodium hydride (60% dispersion in oil, 0.30 g) was gradually added to the resulting solution at room temperature. After this was stirred at room temperature for 3.5 hours, an aqueous solution of 2 N sodium hydroxide (50 ml) was added thereto and stirred for an additional 30 minutes. Water was added to the reaction mixture, and the pH was then adjusted to 6 with 2 N hydrochloric acid. The crystals thus precipitated were collected by filtration, and recrystallized from ethanol to obtain 4-(4-chlorophenyl)-2-(2-propyl-1-imidazolyl)-5-oxazolepropionic acid (1.25 g, 69%) as pale brown needles. mp 174-175 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Propylimidazole, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6177452; (2001); B1;,
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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H5IN2

To a microwave tube was added 4-iodo-l -methyl- 1H-imidazole (2.00 g, 9.62 mmmol) and CuCN (1.03 g, 11.5 mmol) in DMA (12 mL). The reaction mixture was heated at 180 C in a microwave reactor for 45 min. The reaction mixture was concentrated in vacuo. The residue was suspended in EtOAc/sat. NH4Cl/NH4OH (add NH4OH to sat NH4Cl to pH=9) and stirred for 30 min. The organic phase was separated, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 580 mg of the title compound as a light brown solid.

The synthetic route of 71759-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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 33543-78-1, Formula: C6H8N2O2

a solution of 13.3 g of ethyl imidazole-2-carboxylate in 145 ml of anhydrous dimethylformamide is added dropwise over 20 minutes at a temperature of between 20° C. and 25° C. to a suspension of 3.4 g of 80percent sodium hydride in 45 ml of anhydrous dimethylformamide maintained under a nitrogen atmosphere. After stirring for 15 minutes, a solution of 26 g of 2-bromo-5-fluoro-1-indanone in 190 ml of anhydrous dimethylformamide is added dropwise over 10 minutes at the same temperature. The mixture is stirred for 1 hour 30 minutes and then, after slow addition of 100 ml of water, poured over 3800 ml of distilled water and extracted 4 times with a total of 3800 ml of chloroform. The organic extracts are pooled, washed with 950 ml of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. The product obtained (27 g) is chromatographed on 1490 g of neutral silica gel (0.020-0.045 mm) contained in a column 9.6 cm in diameter, eluding under pressure with a dichloromethane-ethyl acetate mixture (70-30 by volume) and collecting 80 ml fractions. Fractions 13 to 70 are pooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. 13.4 g of ethyl 1-(5-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 127° C. The 2-bromo-5-fluoro-1-indanone can be prepared in the following manner:

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, Ethyl 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Iodo-1-trityl-1H-imidazole

A mixture of 4-iodo-1-(triphenylmethyl)-1H-imidazole (Intermediate A, 4.36 g, 9.99 mmol), (2-formylphenyl)boronic acid (1.65 g, 11.00 mmol), Pd(PPh3)4 (1.16 g, 1.0 mmol) and K3PO4 (4.25 g, 20.02 mmol) in DMF (40 mL) and water (8 mL) was stirred at 100 C. for 16 h under N2 atmosphere. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (150 mL*2). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (1% to 25% gradient) to yield 2-(1-trityl-1H-imidazol-4-yl)benzaldehyde as yellow solid (3 g, 72%). MS: m/z=415.1 [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 96797-15-8.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

Example 22 Synthesis of 1-tritylimidazole (5) To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol.) in 50 ml dry methylene chloride. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight. The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water. The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid. Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization). m.p. 214° C.; 1H NMR (200 MHz, CDCl3) delta7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3*C6H5), 7.1-7.2 (m, GH, 3*C6H5), 7.0 (m, 1H, Ph3CNCH=CH), 6.81 (m, 1H, Ph3CNCH=CH); 13C NMR (50 MHz, CDCl3) delta142.3, 139.0, 129.6, 128.2, 128.3, 121.6.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McGill University; US6476216; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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. 41716-18-1 name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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.

Production Example 8 N-[(2-Bromopyridin-4-yl)methyl]-N-cyclobutyl-1-methyl-1H-imidazole-4-carboxamide After a solution of methyl-1H-imidazole-4-carboxylic acid (300 mg), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (1.27 g) and diisopropylethylamine (431 mg) in dimethylformamide (7 mL) was stirred at room temperature for 15 min, N-[(2-bromopyridin-4-yl)methyl]cyclobutanamine (574 mg) was added thereto and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with chloroform, and washed with saturated aqueous sodium hydrogen carbonate solution. After extraction with chloroform, the organic phase was dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20-50:50) to afford the title compound (1.46 g). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.55-2.26 (m, 6H), 3.60-3.81 (m, 3H), 4.56-6.50 (m, 3H), 7.04-8.29 (m, 5H) (ESI pos.) m/z: 349([M+H]+), 351([M+3]+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-imidazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Moriya, Minoru; Yasuhara, Akito; Sakagami, Kazunari; Ohta, Hiroshi; Abe, Kumi; Yamamoto, Shuji; Araki, Yuko; Urabe, Hiroki; Sun, Xiang-Min; US2013/184460; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem