Category: imidazoles-derivatives

Application of 405173-97-9, 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 405173-97-9 as follows.

General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 – 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 – 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion to general procedure 7, 2-(2-aminoethyl)-N-(pyridin-2-ylmethyl)-1 ,3-thiazole-4- carboxamide dihydrochloride (105) (240 mg, 0.72 mmol), 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole (259 mg, 1 .43 mmol) and DIPEA (2.17 ml, 12.53 mmol) in DMF (10 ml) afforded the title compound (64 mg, 22%) as a brown solid after purification by basic prep-HPLC followed by flash column chromatography (eluting with a gradient of 0-10% MeOH / DCM followed by 0.8 M ammonia in MeOH / DCM) 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 8.87 (t, J = 6.0 Hz, 1 H), 8.50 (d, J = 4.6 Hz, 1 H), 8.10 (s, 1 H), 7.74 (td, J = 7.7, 1 .7 Hz, 1 H), 7.44 (s, 2H), 7.33 – 7.21 (m, 2H), 7.10 (dd , J = 5.9, 3.2 Hz, 2H), 4.55 (d , J = 6.0 Hz, 2H), 3.15 (t, J = 6.7 Hz, 2H), 3.02 (t, J = 6.7 Hz, 2H), 2.90 – 2.96 (m, 4H) HPLCMS (Method G): [m/z]: 407.2 [M+H]+

According to the analysis of related databases, 405173-97-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0, 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 2620-76-0 as follows.

Example 5In Example 5, an example of a synthesis method of 4-(9H-carbazol-9-yl)-4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)triphenylamine (abbreviation: YGABIm) which is represented by a structural formula (227) will be described. A synthesis scheme is shown in the following (E5-1). In a 100 mL three-necked flask were placed 1.0 g (2.7 mmol) of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole, 0.96 g (2.7 mmol) of 4-(carbazol-9-yl)diphenylamine (abbreviation: YGA), 0.60 g (6.3 mmol) of sodium tert-butoxide, and 0.050 g (0.086 mmol) of bis(dibenzylideneacetone)palladium(0), and the atmosphere in the flask was replaced with nitrogen.To this mixture were added 15 mL of toluene and 0.050 mL of a 10percent hexane solution of tri(tert-butyl)phosphine. This mixture was stirred at 80° C. for 5 hours. After the stirring, toluene was added to this mixture, and this suspension was subjected to suction filtration through Celite to give a filtrate. The obtained filtrate was washed with water, a saturated sodium hydrogen carbonate solution, and a saturated saline solution in this order. Then, the organic layer and the aqueous layer were separated, and magnesium sulfate was added to dry the organic layer. This mixture was subjected to suction filtration so that the magnesium sulfate was removed to give a filtrate. The obtained filtrate was concentrated to give a compound. The obtained compound was purified by silica gel column chromatography. The silica gel column chromatography was performed by, first, using toluene as a developing solvent, and then using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=5:1) as a developing solvent. The obtained fraction was concentrated to give a compound. The obtained compound was recrystallized with a mixed solvent of chloroform and hexane to give 1.2 g of a light yellow powdered solid in a yield of 74percent.Then, 1.2 g of the obtained solid was sublimated and purified by train sublimation. The sublimation purification was performed under a reduced pressure of 2.7 Pa, with a flow rate of argon at 5 mL/min, at 261° C., and for 14 hours. After the sublimation purification, 1.0 g of a target substance was obtained in a yield of 83percent.By a nuclear magnetic resonance (NMR) method, this compound was confirmed to be 4-(9H-carbazol-9-yl)-4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)triphenylamine (abbreviation: YGABIm), which was a target substance.1H NMR data of the obtained compound is shown below: 1H NMR (CDCl3, 300 MHz): delta=7.30-7.56 (m, 27H), 7.87 (d, J=8.3 Hz, 1H), 8.13 (d, J=7.8 Hz, 2H)

According to the analysis of related databases, 2620-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US8329917; (2012); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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: 2466-76-4

General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fernandez-Garcia, Christian; Powner, Matthew W.; Synlett; vol. 28; 1; (2017); p. 78 – 83;,
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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

To a warm solution of [(eta6-p-cymene)RuCl2]2 (30 mg,0.05 mmol) in ethanol (2.5 mL) a warm solution of HL (16 mg,0.1 mmol) in ethanol (2.5 mL) and triethylamine (13.92 mL), wereadded. The mixture was stirred at room temperature for 4 h. Thebright-yellow product was filtered off, washed with ethanol (2 mL),diethyl ether and dried in vacuo. Yield: 30.2 mg, 70.2%. Anal. Calcdfor C18H19ClN2O2Ru, %: C, 50.06; H, 4.43; N, 6.49. Found, %: C, 50.04;H, 4.54; N, 6.52. IR (ATR, cm1): 3069(m), 3025(w), 2961(s),2906(m), 2756(m), 1642(vs), 1591(m), 1529(s), 1475(s), 1328(s),1229(m). 1H NMR (199.97 MHz, DMSO-d6, delta , ppm): 14.04 (s, 1H,NH), 8.11e8.02 (m, 1H, CHL), 7.64e7.56 (m, 1H, CHL), 7.55e7.42 (m,2H, CHL), 6.06 (d, 1H, JHeH 5.8 Hz, CHcymene), 5.97 (d, 1H,JHeH 5.9 Hz, CHcymene), 5.82 (t, 2H, JHeH 5.7 Hz, CHcymene), 2.69(m, 1H, JHeH 6.9 Hz, eCH(CH3)2), 2.17 (s, 3H, eCH3), 1.11 (dd, 6H,JHeH 7.0 and 9.4 Hz, eCH(CH3)2). 13C NMR (50.28 MHz, DMSO-d6,delta, ppm): 18.68 (eCH3), 22.06, 22.11 (eCH(CH3)2), 31.04(eCH(CH3)2), 77.63, 80.25, 80.34, 81.91 (CHcymene), 98.02 (CeCH3),101.04 (CeCH(CH3)2), 114.10, 118.32, 124.49, 125.69 (CHL), 133.97,140.20 (CeCHL), 145.88 (CeCOO), 164.15 (eCOO). ESI-MS (MeOH):m/z 397.049 [M-Cl]+, 353.059 [M-Cl-CO2]+.

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:
Article; Panti?, Darko N.; Arancrossed D Signelovi?, Sandra; Radulovi?, Sini?a; Roller, Alexander; Arion, Vladimir B.; Grguri?-?ipka, Sanja; Journal of Organometallic Chemistry; vol. 819; (2016); p. 61 – 68;,
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. 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 belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C45H44N6O3

Example 2; 36.0 g (50.3 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-(4-[2-(trityltetrazol-5-yl)-phenyl]phenyl}-methyl imidazole-5-carboxylate (Va) and 3.0 g (75.4 mmol) of NaOH were suspended in 413 ml dimethylacetamide. The suspension was then stirred at room temperature for 20 h and after that 6.9 g (50.3 mmol) of K2CO3 were added. The mixture was cooled to 0C and solution of 15.4 g (70.4 mmol) 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolene in 39 ml of dimethylacetamide were slowly added. The mixture was slowly heated to 50C and stirred at this temperature for 2 h. After esterification was completed, the mixture was cooled to 10 C and poured into a mixture of 625 ml of ethyl acetate and 625 ml of 10 % NaCl, and stirred at 25 C for 15 min. The phases were separated and organic phase was washed 2x with 500 ml of 10 % NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated up to ½ (approximately 270 g) at reduced pressure. To the resulting solution, 80 ml of ethanol and 8.3 ml (100 mmol) of conc. HCl were added and stirred at 24-26C for 3h. To the cooled mixture 600 ml of water was added and pH of the suspension was estimated to 5 by addition of 5 M NaOH. The phases were stirred for 15 min and separated. Water phase was reextracted with 150 ml of ethyl acetate. Collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. 560 ml of ethyl acetate were added and the mixture was evaporated again. After that, 300 ml of ethyl acetate were added and the mixture was cooled to 20 C and stirred for 1h, filtered off and washed with 20 ml of fresh ethyl acetate. The yield of the product (I) was 21 g (75 %).

The synthetic route of 144690-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KRKA, tovarna zdravil, d.d., Novo mesto; EP1816131; (2007); A1;,
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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,1′-Thiocarbonyldiimidazole

A solution of the amine (2.1 g, 8.7 mmol) in anhydrous CH2CI2 (40 ml_) was added dropwise over 2-5 minutes to an ice-NaCI bath cooled solution of 1 , 1 ‘-thiocarbonyldiimidazole (95%, 3.1 g, 17.4 mmol, 2 eq.) in anhydrous CH2CI2 (120 ml_). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1 .5 hours after which time analysis by TLC (5% MeOH in CH2CI2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (13 mL, 91 mmol, 10.5 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (~5 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf Si02 (120 g), 100% CH2CI2? 10% MeOH in CH2CI2) gave the thiourea as an amber oil that solidified to a tacky residue upon standing (2.5 g, 96%).

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DUKE UNIVERSITY; LIEDTKE, Wolfgang; (189 pag.)WO2017/177200; (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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Preparation of ( 1 -methyl- l H-benzimidazol- – l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 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; GLENMARK PHARMACEUTICALS S.A.; LINGAM, Prasada, Rao, V., S.; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; BAJPAI, Malini; GULLAPALLI, Srinivas; DAHALE, Dnyaneshwar, Harishchandra; MINDHE, Ajit, Shankar; RATHI, Vijay, Eknath; WO2011/138657; (2011); 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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H24N2

(2) Add 50 mL of ethanol to a four-neck round bottom flask.Further added 19.35 g (0.05 mol) of N,N-dimethyl(1-bromopropyl)decyl ammonium bromide, 10.42 g (0.05 mol)N-decylimidazole and1 g of tetrabutylammonium bromide,The mixture was heated to 70 C with stirring, and the reaction was stirred for 36 hours, and then ethanol was distilled off under reduced pressure.The solid was washed three times with chloroform.The filter cake was vacuum dried at 60 C for 5 hours to obtain a crude product;The crude product is recrystallized three times in acetone to obtain the product.1-(N,N-dimethylammonium alkylammonium) propyl-3-hydrazinium imidazolium dibromide,The yield was 85.8%.

The synthetic route of 33529-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University of Light Industry; Yang Xuzhao; Wang Jun; Li Yakun; Ping Dan; Zhang Yingying; Wu Shide; (8 pag.)CN109970657; (2019); A;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-16-5, 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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 13 (210 mg, 0.63 mmol), 5-bromothiazole (156 mg, 0.95 mmol), SPhos (26.0 mg, 0.06 mmol), SPhos-Pd-G2 (45.7 mg, 0.06 mmol) and 2 M aq. Cs2CO3 solution (0.793 ml, 1.59 mmol) in DME (4 mL) was heated at 130 °C for 1 h under microwave irradiation. The mixture was diluted with EtOAc (10 mL), dried over MgSO4, and solvent removed under vacuum. The residue was purified by column chromatography (NH silica gel, eluted with 5?17percent EtOAc/hexane) to yield (E)-tert-butyl 3-(4-(thiazol-5-yl)pyridin-3-yl)acrylate (14a tBu ester, 102 mg, 56percent) as a pale yellow solid. This compound was dissolved in TFA (2.0 ml) and stirred at rt for 2 h. After removal of solvent under reduced pressure, the residue was triturated with EtOAc/hexane (1:1) (3 mL) and the resulting precipitate collected by filtation to yield 14a TFA salt (79 mg, 36percent overall) as a colorless solid

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-1-methyl-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Fujimoto, Jun; Hirayama, Takaharu; Hirata, Yasuhiro; Hikichi, Yukiko; Murai, Saomi; Hasegawa, Maki; Hasegawa, Yuka; Yonemori, Kazuko; Hata, Akito; Aoyama, Kazunobu; Cary, Douglas R.; Bioorganic and Medicinal Chemistry; vol. 25; 12; (2017); p. 3018 – 3033;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Method B, Step 3: (7aS,12a1R)-10-fluoro-3-(3-methoxy-4-(4-methyl-1 H- imidazol-1 -yl)styryl)-6,7,7a,8-tetrahydro-5H-indeno[1 ,2- b][1,2,4]oxadiazolo[4,5-a]pyridine (B3, R9 = 4-(4-Methylimidazol-1-yl), R10 = 3- MeO-Phenyl) B2 (0.24g, 0.63mmole) was dissolved in THF and the reaction was cooled to -78C. n-Butyllithium (2.5ml in Hexane, 0.28ml) was added and the reaction was stirred at -78C for 30 minutes. 3-methoxy-4-(4-methyl-1 H-imidazol-1- yl)benzaldehyde (0.136g, 0.63mmole) in 10 ml THF (Pre-cooled to -78C) was added. The reaction was stirred at -78C for 1 hour, then at room temperature for one hour. THF was removed and the residue was partitioned between 100ml EtOAc and 100ml water. The organic layer was washed with water (2x100ml), dried with Na2SO4 and concentrated. The residue was purified by column (EtOAc/hexane from 25/75 to 100/0 in 45 minutes, 12Og silica). Yield: 0.19g, 68%. 1H NMR (CDCI3400 MHz): 7.73 (s, 1 H), 7.50 (dd, J = 8.1 , 5.12 Hz, 1 H), 7.43 (d, J = 16.8 Hz, 1 H), 7.27 (m, 1 H), 7.18 (d, J = 8.1 Hz, 1 H), 7.13 (s, 1 H), 7.00 (m, 3H), 6.52 (d, J =16.1 Hz, 1 H), 3.90 (s, 3H), 3.71 (m, 1 H), 3.30 (dd, J = 16.1 and 5.9 Hz, 1 H), 2.91 (m, 1 H), 2.64 (m, 1 H), 2.38 (d, J = 16.1 Hz, 1 H), 2.30 (s, 3H), 2.06, (m, 1 H), 1.51 (m, 2H), 1.10 (m, 1 H). MS (M+1 ): 445.2.

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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2008/153792; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem