Category: imidazoles-derivatives

Application of 614-97-1, A common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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.

General procedure: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16093-82-6, A common heterocyclic compound, 16093-82-6, name is 1H-Imidazole-2-carboxamide, molecular formula is C4H5N3O, 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 solution of lH-imidazole-2-carboxylic acid amide (360 mg, 3.24 mmol) and phenyl dichlorophosphate (2 mL) was heated at 1700C for 8 min, in a microwaves oven. The reaction mixture was cooled at room temperature and poured into water (50 mL). The solution was cooled at 0C and the pH was adjusted to 11 by addition of NaOH 10 M. Ethyl acetate was added and the phases were separated. The organic layer was dried over sodium sulphate and evaporated in vacuo to provide IH- Imidazole-2-carbonitrile. A solution of lH-imidazole-2-carbonitrile and hydroxylamine (50% sol. in water, 794 muL, 13 mmol) in ethanol (15 mL) was refluxed for 4h. The solvent was removed and the crude N-hydroxy-lH-imidazole-2- carboxamidine was used for the next step without further purification. EPO Yield: quantitative; LCMS (RT): 0.62 min (Method D); MS (ES+) gave m/z: 127.0 (MH+).

The synthetic route of 16093-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2006/123257; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

872-49-1, 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. 872-49-1, name is 5-Chloro-1-methylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Chloro-1-methyl-imidazole (4.0 g, 34.32 mmol) was dissolved in a mixture of 4.0 g of conc. nitric acid and 14 mL of water, and concentrated in vacuo to give a yellow slurry. To this mixture was added dropwise 12 g of conc. sulfuric acid and heated to 95C for 2 hours. Upon cooling, ice was added to the reaction mixture, which was then left standing 10 hours at 5C. The white precipitation was collected by filtration, washed with water, recrystallized from ethanol and dried in vacuo to give compound 60A.

The synthetic route of 5-Chloro-1-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; EP1066286; (2009); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 85692-37-1, A common heterocyclic compound, 85692-37-1, name is 1-(1-Methyl-1H-imidazol-2-yl)ethanone, molecular formula is C6H8N2O, 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.

Step 3-Synthesis of 4-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-ol To a solution of 4-(6-ethynyl-3-methylindazol-1-yl)pyrimidin-2-amine (150 mg, 0.6 mmol) in THF (2 mL) at -78 C. under nitrogen was added 2M LDA in THF (0.75 mL, 1.50 mmol). After 5 minutes, 1-(1-methyl-1H-imidazol-2-yl)ethanone (225 mg, 1.81 mmol) in THF (1.0 mL) was added, and after a further 20 minutes the mixture was allowed to warm to RT and stirred for 1.5 hours. The reaction mixture was then cooled to -78 C. and treated with additional 2M LDA in THF (0.3 mL, 0.6 mmol) and 1-(1-methyl-1H-imidazol-2-yl)ethanone (90 mg, 0.6 mmol). After stirring at RT for 4 hr, the reaction mixture was quenched by addition of saturated aqueous NH4Cl (2 mL). The volatiles were removed in vacuo and the mixture was diluted with DCM (10 ml) and washed with water (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage, 3-12% methanol gradient in DCM) to give the title compound: 1H NMR (500 MHz, DMSO) delta 2.00 (3H, s), 2.57 (3H, s), 3.92 (3H, s), 6.32 (1H, s), 6.77 (1H, s), 6.98 (2 H, s), 7.03 (1H, d, J=5.5 Hz), 7.15 (1H, s), 7.36 (1H, d, J=8.2), 7.84 (1H, d, J=8.2 Hz), 8.25 (1H, d, J=5.5 Hz), 8.84 (1H, s); LC-MS: m/z=+374.05 (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; Genentech, Inc.; US2012/214762; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1403474-70-3, 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. 1403474-70-3, name is Ethyl 2-ethoxy-1-((2′-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of azilsartan ester (VI; Ri= Et) (25 g) and 0.4 N NaOH solution (380 ml) was heated at 70-75C for 90 minutes. The reaction mixture was cooled to 10-15C and the pH was adjusted to 2.5-3.0 with 2 N HC1. The mixture was stirred for 30 minutes at 10- 15C. The solid was filtered, washed with water (100 ml) and dried under vacuum. Yield: 22.0 g;X-ray powder diffraction pattern as depicted in figure 1.

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 2-ethoxy-1-((2′-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LUPIN LIMITED; ANSARI, Shahid, Akhtar; HIRPARA, Hitin, Maganbhai; BHATT, Nikhil, Shashikant; BARIA, Reenaben, Ratansing; YADAV, Ashok, Keshavlal; PATEL, Manishkumar, Baldevlal; WO2014/49512; (2014); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 52099-72-6, The chemical industry reduces the impact on the environment during synthesis 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

To a stirred solution of l-Isopropenyl-l,3-dihydro-benzimidazol-2-one (5g, 28.7mmol) in DMF (20ml) was added methyl acrylate (2.8ml, 31.6mmol) followed by benzyltrimethylammonium hydroxide (Triton B, 40 wt% in MeOH, 3.2ml). The resulting solution was stirred at ambient temperature until the reaction was complete. After this time the reaction was poured into water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic layers were dried (MgSCH), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 30% ethyl acetate/hexanes). The product-containing fractions were combined and concentrated to give 4.8g (64%) of the desired product.

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-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); 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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., name: 4-Iodo-1-trityl-1H-imidazole

Compound 1 (2.2 g, 5.0mmol), o-formylphenylboronic acid(1.2 g, 7.5mmol), K3PO4 (3.2 g, 15mmol), Pd (PPh3)4 (0.6 g, 1.0mmol) is dissolved in DMF/H20 (30mL/6mL). The system is replaced with nitrogen and warmed at 90C, the reaction is stirred overnight. The reaction solution is diluted with ethyl acetate (50mL), wash with saturated brine (25mL X 3), dry over anhydrous sodium sulfate, and dry under reduced pressure. Crude column chromatography (PE: EA = 5:1), and then obtained brown solid compound 2 (810 mg, 39%).

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; Lunan Pharmaceutical Group Co., Ltd.; Zhang Guimin; Guan Yongxia; Li Xin; (15 pag.)CN107556315; (2018); 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. 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2O

To a solution of 1,3-dihydro-1,N-methyl-2-oxobenzimidazole (3.185 g, 21.5 mmol) in DMF (60 mL) is added NaH (60% in mineral oil,1.03 g, 25.78 mmol) portionwise at 0 C. After stirring at 0 C for 30 min.2,4-dichloropyrimidine (3.20 g, 21.5 mmol) is added, and the mixture is allowed to stir at 15 C for 12 hrs. The resulting mixture is quenched with water (200 mL) and the mixture is extracted with EtOAc (100 mL x 3), and washed with water (100 mL x 4), dried with Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (petroleum ether: EtOAc =10:1), to give 2-chloro-4-(1,3-dihydro-3,N-methyl-2-oxobenzimimidazol-1-yl)pyrimidine.

According to the analysis of related databases, 1849-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); 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. 857070-66-7, name is (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, A new synthetic method of this compound is introduced below., Recommanded Product: (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol

A mixture of b-3 (0.069 mol) and N-propylamino-morpholine (0.207 mol) was stirred at 125C for 4 hours, and then taken up in CH2C12/CH3OH. The organic layer was washed with a 10% solution OfK2CO3 in water, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue (37 g) was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 90/10/0.5; 20-45mum). The pure fractions were collected and the solvent was evaporated, yielding 16.5g of intermediate b-4 (82%).

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; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5465-29-2, These common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, 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 50 ml of water, 450 ml of concentrated sulfuric acid (i.e., 90% concentration) was added dropwise, 50.0 g of 2-propylbenzimidazole was added, and 300 ml of a 30% aqueous solution of hydrogen peroxide was added dropwise. The reaction was exothermic to reflux and the dropping speed was maintained to keep the reaction solution boiling.After completion, the reaction was continued for 3 hours.Add water 400ml, cold to room temperature.The solid was precipitated and stirred at 0-5 C for 3 hours, filtered, washed with water, washed with 100% of 5% sodium sulfite aqueous solution and dried to constant weight to give 2-propylimidazole-4,5-dicarboxylic acid as a white solid (21.7 g, 35%), HPLC purity 89.4%,

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huanggang LUBAN Pharmaceutical Co.,Ltd. (LUBAN); YANG, XIAOLONG; LIU, XIANGQUN; LI, QIANG; CHEN, QIAN; YANG, TIEBO; (17 pag.)CN104262260; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem