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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-1-methyl-1H-imidazole

intermediate 2: step c(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanoneTo a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo- 1 -methyl- 1 H-imidazole (47.96 g, 297.9 mmol), followed by TI1F (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1 .3 in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C in an ice bath. To this mixture was added a solution of N-methoxy-N-m.ethyl-6- (irifiuoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 2: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C) to afford an orange mixture. After addition, the reaction was warmed 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 and carefully quenched with 2 N aqueous HCl to pH = 7, quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), phases split and the organic layer was washed with brine (2 x 200 mL), dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and suspension was filtered to provide 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 NV; BARBAY, Kent; EDWARDS, James, P.; KREUTTER, Kevin, D.; KUMMER, David, A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald, L.; WOODS, Craig, R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell, D.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
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Electric Literature of 96797-15-8,Some common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, molecular formula is C22H17IN2, 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.

58] Intermediate 14 301[59] A solution of 4-iodo-l-tritylimidazole (commercially available) 5.2 g, 11.94 mmol) in dichloromethane (80 mL) at -10 0C was treated with ethyl magnesium bromide (3.98 mL, 11.94 mmol, 3M in ether) and allowed to react for 45 m. A solution of quinoline-8-carbaldehyde, (Intermediate 11) (1.5 g, 9.55 mmol) in dichloromethane was added via syringe at -10 0C and stirred for 16 h at room temperature. The mixture was quenched with water (50 mL) and a sat. solution of ammonium chloride (50 mL) and subjected to an aqueous work-up. The residue was purified by chromatography on silica gel with 3% NH3-MeOH: CH2Cl2 to give to give quinolin-8-yl(l-trityl-lH-imidazol-5- yl)methanol, (Intermediate 12) as a solid, (3.7 g 82.7%).

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

Reference:
Patent; ALLERGAN, INC.; WO2008/147786; (2008); A1;,
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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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 1-Decyl-1H-imidazole

Equipped with a stirrer, a thermometer, a three-necked flask was added 1.67 g (8.0 mmol) N- decyl-imidazole, 0.56 g (4.4 mmol) 1,3- dichloro-2-propanol, at 115 ~ 125 C The reaction was stirred after, TLC tracking progress of the reaction, the reaction of about 8 ~ 12 h, the crude product was mixed with chloroform and ethyl acetate solvent was recrystallized to give a white powdery solid 1,1′-didecyl-3,3 ‘- (2- hydroxy-1,3-propylene) imidazole hydrochloride 1.42 g, yield 65.2%.

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; Qiqihar university; Wang, LiYan; Deng, QiGang; Zheng, YongJie; Huo, shichao; Liu, Jia; Sun, zhu; (10 pag.)CN103951702; (2016); B;,
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Application of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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 18 preparation of 6 – (4-iodo -1H-imidazol-1-yl) pyrimidin-4-amine (intermediate II-18)

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; East China University of Technology; Mao, Fei; Wang, Huan; Li, Xiaokang; Zhang, Haiyan; Lu, Zhengyu; Li, Jian; (43 pag.)CN105418592; (2016); A;,
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Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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: 7189-69-7

N,N? – sulfuryldiimidazole (5.00 g, 25.2 mmol, 1.0 eq) was then suspended in 50 mL of anhydrous dichloromethane at 0C under N2. Methyltrifluoromethanesulfonate (2.56 mL, 22.7 mmol, 0.9 eq) was added dropwise over 15 minutes at 0C. The reaction stirred at 0C for 2 hours. The solvent was decanted off and 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate was isolated as a white solid was washed three times each with 50 mL of cold dichloromethane and dried under high vacuum for 10 minutes and immediately used in the next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7189-69-7, its application will become more common.

Reference:
Patent; UNIVERSITY OF DELAWARE; GRIMES, Catherine, Leimkuhler; MELNYK, James, E.; LIANG, Hai; DEMEESTER, Kristen, E.; (65 pag.)WO2016/172615; (2016); A1;,
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Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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. Quality Control of 2-(1H-Imidazol-1-yl)ethanol

2-(1H-benzo[d]imidazol-1-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide-HCl (EDC-HCl) (2.20 g, 11.5 mmol) was added solid all at once to a magnetically stirred solution of naproxen (2.30 g, 10.0 mmol), 1-(2-hydroxyethyl)imidazole (1.12 g, 10.0 mmol) and 4-Dimethylaminopyridine (61 mg, 0.5 mmol) in dry tetrahydrofuran (50 mL) cooled in an ice bath and kept under nitrogen. The reaction mixture was stirred in an ice bath for 30 min and at ambient temperature. More EDC-HCl (400 mg, 2 mmol) was added after 13 hrs, 17 hrs. After stirring for 22 hrs at room temperature the mixture was concentrated and the residue partitioned between water (50 mL), saturated NH4Cl (20 mL) and EtOAc (120 mL). The organic layer was washed with 50% saturated NH4Cl (2*50 mL), 50% saturated NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried and concentrated. The oily residue was purified by Flash Chromatography using ethyl acetate and heptanes as eluent afforded a colourless oil (2.74 g, 84%) after drying in high vacuum. The oil was crystallised from ether and recrystallised from Tert-butylmethylether (?20 mL, seeded) to afford the title compound as a colourless solid (2.21 g, 68.3%). Mp. 60.6-61.3 C. 1H NMR (400 MHz, DMSO) delta 7.80 (d, J=9.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.68 (d, J=1 Hz, 1H), 7.51 (s, 1H), 7.33 (dt, J=5.5, 3 Hz, 1H), 7.30 (d, J=2.5 Hz, 1H), 7.17 (dd, J=9, 2.5 Hz, 1H), 6.98 (t, J=1 Hz, 1H), 6.78 (t, J=1 Hz, 1H), 4.34-4.12 (m, 4H), 3.92 (q, J=7 Hz, 1H), 3.88 (s, 3H), 1.45 (d, J=7 Hz, 3H). 13C NMR (101 MHz, DMSO) delta 173.52, 157.19, 137.40, 135.30, 133.33, 129.15, 128.37, 128.25, 126.99, 126.20, 125.63, 119.46, 118.73, 105.69, 63.74, 55.15, 44.94, 44.35, 18.19.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1615-14-1, its application will become more common.

Reference:
Patent; Larsen, Claus Selch; Larsen, Susan Weng; Thing, Mette Agergaard; Kristensen, Jesper Langgaard; Jensen, Henrik; ?stergaard, Jesper; US2014/315960; (2014); A1;,
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24134-09-6, name is 5-Bromo-1,2-dimethyl-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: C5H7BrN2

General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

The synthetic route of 24134-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
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1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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. SDS of cas: 1450-93-7

EXAMPLE 2 5-(4-Pyridyl)imidazo[1,2-a]pyrimidine A mixture of 5.29 g of 2-aminoimidazole hemisulfate, 3.28 g of anhydrous sodium acetate and 7.04 g of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one (prepared according to the procedure of Example 63 in U.S. Pat. No. 4,281,000) in 100 ml of glacial acetic acid was heated under reflux for 16 hours. The procedure of the above Example 1 was followed and the title compound was obtained as pale yellow needles, mp 244-245 C.

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4551530; (1985); A;,
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Electric Literature of 144690-33-5, The chemical industry reduces the impact on the environment during synthesis 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

Example 6; Preparation of 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic Acid DihydrateEthyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methyl imidazole-5-carboxylate (100 g) was dissolved in isopropyl alcohol (500 ml). Separately prepared solution of potassium hydroxide (32 g) in IPA (1.0 L) was added slowly to above solution at room temperature. Reaction mass was stir for 2-4 hrs at 30-40 C. Isopropyl alcohol was distilled under reduced pressure. Water (400 mL), sodium chloride (40 g) & ethyl acetate (1.0 L) was added to the residue. Separate the two layers & aqueous layer was extracted with ethyl acetate (3¡Á500 ml). Combined ethyl acetate layer was washed with sodium bicarbonate solution (3¡Á500 mL) & dried (Na2SO4). Distilled off ethyl acetate under reduced pressure completely & residue thus obtained was recrystallized from acetonitrile to get 4-(1-hydroxy-1-methylethyl)-2 propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic acid dihydrate (95 g).HPLC purity=99.0%Moisture Content5.0%.

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 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ramanjaneyulu, Gorantla Seeta; Mohan, Bandari; Ray, Purna Chandra; Sethi, Madhuresh Kumar; Rawat, Vijendra Singh; Krishna, Yerramalla Raja; Lakshminarayana, Vemula; Srinivas, Mamidi; US2009/281327; (2009); A1;,
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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. 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 53484-15-4

To a solution of 5-bromo-1-methyl-1H-benzo[d]imidazole (200 mg, 0.33 mmol, 1 eq.) in 1,4-dioxane (10 mL) was added 5-(4,4,5,5-bis(pinacolato)diboron (287 mg, 1.13 mmol, 1.2 eq.), KOAc (276 mg, 2.82 mmol, 2 eq.), PdCl2(dppf).DCM (76 mg, 0.09 mmol, 0.09 eq.). The reaction mixture was deoxygenated with N2 and the reaction mixture was stirred at 80 C. for 16 h. The reaction was monitored by LCMS and found to be complete after 18 h. The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with ethyl acetate (2*50 mL). Combined organic layer was washed with brine (20 mL) and dried over sodium sulfate. Removal of solvent under reduced pressure gave crude which was purified by Combi-Flash (0-100% EtOAC-Hexane) to afford the desired product (120 mg, 49%) as brown oil.

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 53484-15-4.

Reference:
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (314 pag.)US2019/23702; (2019); A1;,
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Imidazole | C3H4N2 – PubChem