Imidazoles-derivatives

Synthetic Route of 401567-00-8, 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. 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4.1.19. 5-Cyano-2-(4-isopropoxyphenoxy)-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole and 6-cyano-2-(4-isopropoxyph-enoxy)-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole (18) To a solution of 17 (0.60 g, 2.0 mmol) and 4-isopropoxyphenol(0.46 g, 3.0 mmol) in DMF (10 mL) was added Cs2CO3 (1.9 g,5.9 mmol), and the mixture was stirred at room temperatureovernight. The reaction was quenched by addition of water, andthe resulting mixture was extracted with AcOEt. The combinedorganic layer was washed with brine, dried over Na2SO4 and con-centrated under reduced pressure. The residue was puried bysilica gel column chromatography (n-hexane/AcOEt = 3:1) toafford the product 18 (0.83 g, 99%, 1:1 regioisomeric mixture)asa pink oil.1H NMR (500 MHz, CDCl3) d 7.83 (s, 1/2H), 7.68 (d, J = 1.1 Hz,1/2H), 7.59 (d, J = 8.0 Hz, 1/2H), 7.51-7.47 (m, 1H), 7.44 (d,J = 8.0 Hz, 1/2H), 7.26-7.23 (m, 2H), 6.96-6.93 m, 2H), 5.56 (s,1H), 5.56 (s, 1H), 4.56-4.51 (m, 1H), 3.68-3.64 (m, 2H), 1.36 (d J = 6.0 Hz, 6H), 0.99-0.93 (m, 2H), 0.01 to 0.04 (m, 9H); ESI-TOF-HRMS calcd for C23H29N3O3Si (m/z) [M+Na]+ 446.1870, found446.1870.

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-Chloro-1H-benzo[d]imidazole-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
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 51605-32-4 as follows. Recommanded Product: Ethyl 5-methyl-1H-imidazole-4-carboxylate

A. To a stirred suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (2.00 g, 13.0 mmol) in acetonitrile (25 mL) and chloroform (25 mL) was added N-bromosuccinimide (2.31 g, 13.0 mmol). The reaction mixture was stirred under nitrogen atmosphere for 20 h, then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluding with 50percent ethyl acetate in hexanes to afford ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate as a light yellow solid (1.88 g, 62percent): 1H NMR (300 MHz, CDCl3) delta 4.35 (q, J=7.1 Hz, 2H), 2.51 (s, 3H), 1.37 (t, J=7.1 Hz, 3H); MS (ES+) m/z 233.1 (M+1), 235.1 (M+1).

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dales, Natalie; Fonarev, Julia; Fu, Jianmin; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Pokrovskaia, Natalia; Raina, Vandna; Sun, Shaoyi; Zhang, Zaihui; US2009/156615; (2009); A1;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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. COA of Formula: C12H12N2O2

Method Aq, Step 6:Comopund Aq6 (0.46 g) in CICH2CH2CIZMeCN (20 rnL, 1/1) was treated with PPh3-HBr (0.73 g) and heated for 5 hours before solvent was removed. The residue was taken up in THF/DMF (27.5 mL, 10/1 ) and 3-rnethoxy~4-(1-(4- methylinidazolyf))benza.de?yde (0.29 g) was added. The mixture was cooled to 0 0C and LHMDS (4.5 mL, 1.0 M in THF) was added dropwise. The mixture was stirred at 0 0C for 1 hour and then room temperature for 1 hour before NH4CI was added to quench the reaction. The residue was diluted with EtOAc. The aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4, and concentrated to give the crude product which was purified by column chromatography etuting with EtOAc/hexanes to yield compound Aq7 (0.13 g).

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

Reference:
Patent; SCHERING CORPORATION; ZHU, Zhaoning; GREENLEE, William J.; HUANG, Xianhai; QIN, Jun; LIU, Xiaoxiang; LI, Hongmei; ZHOU, Wei; PALANI, Anandan; ZHU, Xiaohong; VICAREL, Monica L.; MANDAL, Mihirbaran; SUN, Zhong-Yue; BENNETT, Chad E.; MCCRACKEN, Troy M.; GALLO, Gioconda; WO2010/56849; (2010); A1;,
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Reference of 41716-18-1, The chemical industry reduces the impact on the environment during synthesis 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a solution of intermediate 12-g (610 mg, 1.17 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (177 mg, 1.40 mmol), HATU (624 mg, 1.64 mmol) and DIPEA (816 uL, 4.69 mmol) and the reaction mixture was stirred at 0¡ã C. for 2 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 13-a as a white foam.

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-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]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 760212-58-6, HPLC of Formula: C19H13BrN2

1.0 g (2.9 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 1.2 g (3.2 mmol) of 9,10-diphenylanthracene-2-boronic acid, and 0.067 g (0.058 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 1. 6 g of a greenish white solid (90% yield) . Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 598 with respect to a molecular weight of 598.24.

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:
Patent; IDEMITSU KOSAN CO., LTD.; EP1734038; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 705-09-9, A common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

A mixture of the material so obtained, 2-difluoromethyl-lH’-benzimidazole (0.435 g), potassium carbonate (1.36 g) and DMF (15 ml) was stirred under nitrogen and heated to 1100C for 24 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. There was thus obtained 4-chloro-2-(2-difluoromethylbenzimidazol-l-yl)- 6-[(3iS)-3-methylmorpholin-4-yl]pyrimidine (0.76 g) which was used without further purification.

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; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32086; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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. name: 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole

Preparation of Compound F[186] Compound F-2 (38.6g, 110mmol), potassium acetate (32.4g, 330mmol), bis(pinacolato)diboron (36.5g, 143mmol), 1,4-dioxane (390mL), and PdCl2(dppf) (1.8g, 2mmol) were mixed and stirred at 80 for 18 hours, and then cooled at room temperature. Water (400mL) was added to the reactant and stirred. After stirring, an organic layer was extracted by adding saturated sodium chloride aqueous solution and ethyl acetate, dried over magnesium sulfate, and treated with activated charcoal, followed by filtering with celite. A solid prepared by concentrating the filtrate under reduced pressure was re-crystallized, thereby obtaining Compound F (36g, 82%).[187] 1H NMR (CDCl3) d 7.92(d, 1H), 7.76(d, 2H), 7.59(d, 2H), 7.56-7.45(m, 3H), 7.41-7.29(m, 4H), 7.27(s, 1H), 1.35(s, 12H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2620-76-0, its application will become more common.

Reference:
Patent; ALPHA CHEM CO., LTD.; NAM, Hyun Goog; LIM, Dae Won; KIM, Jae Yong; PARK, Sang Mi; JANG, Seung Hee; LEE, Sang Youn; HAM, Ju Seok; CHO, Kyu Oh; KIM, Hyun Don; WO2013/180376; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-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 95470-42-1, Recommanded Product: Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

(2) Ethyl 2-bromo-4-methyl-i H-imidazole-5-carboxylate (5lene (4.56 g, 25.8 nmol) were added thereto, and the mixmre g, 21.45 mmol) was dissolved in DMF (40 mE), potassium carbonate (5.93 g, 42.9 mmol) and 1 -(chloromethyl)naphthaNwas stirred at 80¡ã C. for 2 hours. After the reaction, water wasThe organic layer was washed with samrated aqueous sodiumadded and the mixture was extracted twice with ethyl acetate.chloride and dried over anhydrous sodium sulfate. Afier con-centrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-4-methyl-1 – (naphthalen-1 -ylmethyl)-i H-imidazole-5-carboxylate (3.2510129] ?H-NMR (CDC13) oe: 8.01 (1H, d, J=8.3 Hz), 7.91(1H, d, J=7.8 Hz), 7.77 (1H, d, J 8.3 Hz), 7.63-7.53 (2H, m),7.33 (1H, t, J=7.6 Hz), 6.43 (1H, dd, J=7.3, 1.0Hz), 6.07 (2H,s), 4.13 (2H, q, J=7.i Hz), 2.58 (3H, s), 1.11 (3H, t, J=7.i Hz);10130] ESI-MS mlz=373 (M+H).

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:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 30148-21-1,Some common heterocyclic compound, 30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, molecular formula is C7H10N2O2, 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.

IM-1 (1.8 g) was dissolved in concentrated H2S04 (5 mL) and cooled to 0C. Nitric acid (90%, 5 mL) was slowly added and the solution warmed to room temperature and then refluxed at-20C for 1.5 hr. The reaction was quenched by pouring onto ice (50 mL). The resulting blue solution was extracted with DCM, dried over sodium sulphate, and evaporated under vacuum to yield a tanned and oily product. The residue was precipitated with CCL4 : EtOH (1 : 1, 5 mL) to yield the product as white crystals. Yield (1.0543 g, 45%). H NMR (DMSO): 6 8.61 (s, 1H), 4.33 (q, 2H, J=6. 4 Hz), 3.97 (s, 3H), 1.29 (t, 3H, J=6. 0 HZ). 13C (DMSO) : 158.2, 145.4, 135.3, 127.4, 62.2, 37.3, 14.5.

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

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 137049-00-4, 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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of N-[4-methyl-5-(lH-pyrazol-4-yl)-l,3-thiazol-2-yl]acetamide, compound (3) (44 mg; 0.2 mmol; 1 eq.), 1 -methyl- lH-imidazole-4-sulfonyl chloride (36 mg; 0.2 mmol; 1 eq.) and N,N-diisopropylethylamine (0.1 ml; 0.6 mmol; 3 eq.) in DCM (2 ml) was stirred overnight at RT. The reaction mixture was diluted with DCM and washed with water and brine. Organic phase was dried over MgSO4, filtered and evaporated. The resulting crude product was purified by flash chromatography (CHCl3ZMeOH gradient from 100:1 to 50: 50), affording compound (8) as light yellow solid (35 mg; 47.5 %). 1U NMR (DMSO-d6) delta 2.12 (s, 3H), 2.32 (s, 3H), 3.72 (s, 3H), 7.86 (m, IH), 8.06 (s, IH), 8.30 (m, IH), 8.47 (s, IH), 12.11 (br s, IH). M”(ESI): 365.25; M+(ESI): 367.23. HPLC, Rt: 2.31 min (purity: 98.4%).

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-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LABORATOIRES SERONO S.A.; WO2007/82956; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem