Category: imidazoles-derivatives

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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., Safety of 1H-Imidazole-4,5-dicarboxylic acid

General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Anuj; Banerjee, Somesh; Roy, Partha; Sondhi; Sharma, Anuj; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 501 – 504;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3314-30-5,Some common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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 flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzo[d]imidazole-2-carbaldehyde, its application will become more common.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 22884-10-2, Product Details of 22884-10-2

Step 1: methyl 14-cyclohexl-3-fluoro-6-( 1 H-imidazol-1 -ylacetyl)-5.6,7,8-tetrahydroindolo[2.] -a] (2,5 lbenzodiaz.ocine-11 -carboxylate; To a solution of 1 eq of methyl-14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,l- a][2,5]benzodiazocin-l 1-carboxylate (prepared as described in Example 18, Step 5 ) in DCM (0.06 M), 1.1 eq of imidazo-1-yl acetic acid in DCM (0.05 M), 3 eq of DIPEA and 1.5 eq of TBTU were added and the mixture stirred at RT overnight. Volatiles were removed in vacuo and the crude material was used in the next step without further purification; MS (ES+) m/z 515 (M+Eta)+. EPO Step 2: 14-cyclohexyl-3-fluoro-6-(lH-imidazol-l-ylacetyl)-5.6.7,8-tetrahydroindolof2.1- alf2.5 Ibenzodiazocine- 11 -carboxylic acid

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-(1H-Imidazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1402838-08-7, The chemical industry reduces the impact on the environment during synthesis 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, I believe this compound will play a more active role in future production and life.

Compound 4 (196 mg, 0.51 mmol) was dissolved in 10 mL of anhydrous tetrahydrofuran, and 30.5 mg of sodium hydride was added on an ice bath, and the mixture was warmed to room temperature and stirred for 1 hour. A solution of compound 4a (211 mg, 0.51 mmol) in 5 mL of anhydrous tetrahydrofuran was added to the reaction flask in an ice bath. The mixture was warmed to room temperature, stirred overnight, quenched with saturated ammonium chloride, added with 100 mL of water and extracted with dichloromethane (50 mL×3). The combined extracts were washed with saturated brine, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give Compound 5 (134 mg, yield 39%).

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-(1-Trityl-4-imidazolyl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zhang Guimin; (92 pag.)CN107488179; (2017); 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 6160-65-2 as follows. Computed Properties of C7H6N4S

To a suspension of 4-bromo-3-chloro-5-(trifluoromethyl)aniline (15 g, 54.7 mmol, Eq: 1.00) in dichloromethane (13.2 g, 10.0 ml, 155 mmol, Eq: 25.3) at 0, was added 1,1′- thiocarbonyldiimidazole (11.7 g, 65.6 mmol, Eq: 1.2) The reaction was gradually warmed to room temperature and stirred overnight. The reaction was concentrated and chromatographed (220g Redisep, 5 to 15% dichloromethane/hexane) to give 13.84 g (80%) pale yellow oil.

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135422; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39021-62-0, 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial equipped with a stir bar was charged with the recovered amine 62 and product mixture (0.330 mmol, 1 equiv.), 43.3 mg of l-methyl-lH-imidazole-4-carbaldehyde (0.390 mmol, 1.2 equiv.), 0.019 mL of CH3COOH (0.330 mmol, 1 equiv.) and 3.4 mL of CH2CI2 and stirred at rt for 3 h. Then 111 mg of NaBH(OAc)3 (0.520 mmol, 1.6 equiv.) was added. After stirring at rt for 12 h, the reaction mixture was quenched by addition of sat. NaHCCb solution and sat. Na2CCb sol., and the product was extracted with CH2CI2 (3x) and dried over Na2S04. The crude product was purified on silica gel column (12 g) using 0-30 % MeOH in EA as eluent affording 116 mg (43%) of N-((S)-3-((R)-3-(((4-(l,3-dioxoisoindolin-2-yl)butyl)((S)-5,6,7,8-tetrahydroquinolin-8- yl)amino)methyl)-4-((1 -methyl- lH-imidazol-5-yl)methyl)piperazin- 1 -yl)- 1 -phenylpropyl)-4,4- difluorocyclohexane-l -carboxamide 78 as a yellowish foam.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-5-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; ALTAS TAHIROVIC, Yesim; WILSON, Lawrence; PELLY, Stephen Christopher; (102 pag.)WO2019/183133; (2019); 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. 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., HPLC of Formula: C11H10F3N3

General procedure: A suspension of methyl 4-methyl-3-(4-(pyridin-3-yl)thiazol-2-ylamino)benzoate (325 mg, 1mmol) and 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (241 mg, 1 mmol) in 10 mL anhydrous THF was cooled to -20 C, a solution of tBuOK (672 mg, 6 mmol) in 10 mL anhydrous THF was added. The reaction mixture was warmed to room temperature slowly and stirred at r.t. for 10 h. The reaction was quenched by adding brine, extracted by E.A., the organic phase were combined, then remove the solvent and the residue was purified by column chromatography on silica gel to afford the title product as a white solid (459 mg, 86%).

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Deping; Zhang, Zhang; Lu, Xiaoyun; Feng, Yubing; Luo, Kun; Gan, Jirong; Yingxue, Liu; Wan, Junting; Li, Xiang; Zhang, Fengxiang; Tu, Zhengchao; Cai, Qian; Ren, Xiaomei; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 21; 7; (2011); p. 1965 – 1968;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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: Two different solutions for feeds A and B were separately prepared in 2 mL vial equipped with a Teflon septum and magnetic stir bar. Feed A: [Ir(dtbbpy)(ppy)2][PF6] (2.00 lmol, 0.01 equiv) and Boc-Pro-OH (0.3 mmol, 1.5 equiv) in 1 mL of DMA; Feed B: NiCl2 glyme (0.02 mmol, 0.1 equiv), 4,4′-di-tert-butyl-2,2′-bipyridyl (0.03 mmol, 0.15 equiv), the corresponding aromatic halides (0.20 mmol, 1.0 equiv), DBU (0.3 mmol, 1.5 equiv) in 1 mLof DMA. The two solutions were degassed by bubbling nitrogen stream for 20 min. Feeds A and B were injected simultaneously into the photoreactor, mixed in a T-mixer, and passed through a 10 mL residence time coil (0.8 mm inner diameter, 4 m length, fluoropolymer tube) irradiated with blue LED 450 nm and heated atthe indicated temperature. The reaction mixture collected from the output was diluted with saturated aqueous NaHCO3 solution,extracted with Et2O (3 10 mL). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentratedin vacuo. Purification of the crude product by flash chromatography on silica gel using as eluent heptane/ethyl acetate afforded the desired product.

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

Reference:
Article; Abdiaj, Irini; Alcazar, Jesus; Bioorganic and Medicinal Chemistry; vol. 25; 23; (2017); p. 6190 – 6196;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57090-88-7, 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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 2-bromo-l-(2,4-difluorophenyl)ethanone (63.1 g, 269 mmol) and 4-cyano- IH- imidazole (25.0 g, 269 mmol, 1.0 eq) in acetonitrile (200 mL) was added NN-diisopropylethylamine (93.81 mL, 69.4 g, 537 mmol, 2.0 eq) and zinc(II) chloride (3.66 g, 26.86 mmol, 0.10 eq) at 30C. The reaction mixture was stirred at 70 C for 12 hours. The reaction mixture was filtered and concentrated in vacuum. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate =1 :1) to give a mixture of desired 3-[2-(2,4-difluorophenyl)-2-oxo-ethyl]imidazole-4-carbonitrile and its regioisomeric by-product 1- [2-(2,4-difluorophenyl)-2-oxo-ethyl]imidazole-4-carbonitrile as an approximately 40:60 mixture (total : 30.0 g, combined yield: 45%).

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, 1H-Imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; MILLER, Ricarda; GENIX, Pierre; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; (124 pag.)WO2018/60074; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 22884-10-2, These common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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.

To a 50 mL flask was added 4-chloro-orthozilidine 1c (1 mmol), alpha-bromo-tert-butyl ketone (1.2 mmol), and potassium carbonate (1.5 mmol), and reacted at 45 C, The reaction solvent was chloroform (20 mL). After reacting for 2 hours, diphenylmethylphosphine (1.5 mmol) was further added, and the reaction was carried out at 30 C. After the reaction was continued for 3 hours, the solvent chloroform was removed under reduced pressure. The residue was transferred to a solution of triphenylphosphine (2.5 mmol) and iodine (2.5 mmol) in chloroform (15 mL). After reacting for 2 hours, after completion of the reaction, the solvent chloroform was removed under reduced pressure. Residue column chromatography gave 0.223 g of the title compound 2c. The yield was 71%.

Statistics shows that 2-(1H-Imidazol-1-yl)acetic acid is playing an increasingly important role. we look forward to future research findings about 22884-10-2.

Reference:
Patent; China Three Gorges University; Wang Long; Yang Qingqing; Li Yongshuang; Li Dejiang; (8 pag.)CN109265448; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem