Tag: M.W=100-200

Application of 492-98-8, 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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 16: Synthesis of (tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(ppy)2BIm]2) [0307] [0308] Under argon atmosphere, into a 100 mL Schlenk flask equipped with a stirrer were placed 322 mg (0.30 mmol) of di-mu-chloro-tetrakis(2-phenylpyridinato) diiridium(III), 40 mg (0.30 mmol) of 2,2′-biimidazole and 60 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 13 hours. Subsequently, 83 mg (0.63 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 24 hours. After the completion of the reaction, tetrahydrofuran was distilled off under reduced pressure, and then methylene chloride was added to the residue, and the insoluble substance was removed by filtration. The filtrate was concentrated under reduced pressure. The resultant crude reaction product was subjected to column chromatography with alumina (developing solvent: methylene chloride / hexane (volume ratio; 3/1) : 0.5 % triethylamine) for purification, to provide 113 mg of the desired compound as a yellow solid. (Yield: 33 %) The desired compound obtained was a mixture of isomers, and the product ratio was Isomer 1 (main product) : Isomer 2 = 61:39. [0309] Additionally, tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III) was a novel compound, which had the following properties: [0310] 1H-NMR (400MHz, C4D8O, delta (ppm)) Isomer 1; 8.18 (dd, 4H), 7.86 (d, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.38 (dd, 4H), 6.11 (s, 4H) Isomer 2; 7.92 (d, 4H), 7.78 (dd, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.32 (dd, 4H), 6.13 (s, 4H) FD-MS (M/Z): 1132 M+

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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. Safety of 5-Phenyl-1H-imidazol-2-amine

General procedure: The (5-benzoyl-1-methyl-1H-pyrrol-2-yl)acetic acid (6)(1 mmol) was dissolved in dry DMF. To this TBTU (2mmol) was added and stirred for 30 min under nitrogenatmosphere. Then 4-aryloxazol-2-amine (7)/4-arylthiazol-2-amine (8)/4-aryl-1H-imidazol-2-amine (9) (1 mmol) followedby DIPEA (0.5 ml) were added and the reactionmixture was heated at 50 C for 6 h. After completion ofreaction (progress of reaction was monitored by TLC) thecontents were allowed to cool and poured into ice water.The resultant solid was filtered, dried and recrystallizedfrom 2-propanol.

The synthetic route of 5-Phenyl-1H-imidazol-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sowmya, Donthamsetty V.; Basha, Shaik Sharafuddin; Devi, Palampalli Uma Maheswari; Lavanyalatha, Yerraguravagari; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 5; (2017); p. 1010 – 1021;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of mutilin (93g, 0.29 mole) in EtOAc (1 L) was cooled to -45 0C (CH3CN/dry ice bath) with mechanical stirring under nitrogen. Trifluoroacetyl imidazole (Aldrich, 5 x 1Og ampules, 5Og, 0.30 mole) was then added dropwise over 30-45 minutes. After stirring for 1 hour, TLC (10% EtOAc/hexanes) showed complete consumption of mutilin. The mixture was allowed to ward to – 200C, and was then washed with IN HCl (2 x 30OmL), water, brine and then was dried over magnesium sulfate and filtered. After concentration to 300-40OmL, IL of hexanes was added with stirring. The precipitated product was filtered and washed with hexanes (IL) to afford pure 11-OTFA-mutilin as a white crytalline solid (55g). Additional product was obtained by evaporating the filtrate, and stirring the residue in ethyl ether (10OmL), and diluting with hexanes (40OmL). Filtration and washing with hexanes gave a second crop (47g) which was ~90% pure by NMR.

The synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/62334; (2007); A2;,
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. 51-17-2, name is 1H-Benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6N2

To a stirred solution of 1H-benzo[d]imidazole (2 g, 16.94 mmol) in acetic acid (25 mL) under an inert atmosphere was added 10% Pd/C (50% wet, 600 mg) at room temperature. The reaction mixture was stirred at 90-95 C. under a hydrogen atmosphere (75 PSI) for 24 h. After consumption of starting material (by TLC), the reaction mixture was filtered through a pad of celite and the pad was washed with EtOAc (100 mL). The filtrate was basified with saturated sodium bicarbonate solution (100 mL) and extracted with EtOAc (2*100 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain 4,5,6,7-tetrahydro-1H-benzo[d]imidazole (800 mg, 6.55 mmol, 40%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.52 (brs, 1H), 7.35 (s, 1H), 2.45 (brs, 4H), 1.74-1.67 (m, 4H)

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 51-17-2.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; (93 pag.)US2018/186773; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 172499-76-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 172499-76-2 name is Ethyl 3-(1H-imidazol-2-yl)propanoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A suspension of tBuOK (1.1 equiv. or 2.2 equiv.) and the imidazole derivative (1.0 equiv.) in DMF (6 mL/mmol) was stirred at rt for 1 h. The reaction mixture was treated with the corresponding alkyl bromide or alkyl mesylate (1.3 equiv. or 2.0 equiv.) and the temperature was raised up to 60 C and stirred at this temperature for 72 h. The solution was then diluted with EtOAc (20 mL/mmol) and washed three times with brine and H2O. The organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by CC.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-(1H-imidazol-2-yl)propanoate, and friends who are interested can also refer to it.

Reference:
Article; Kerscher-Hack, Silke; Renukappa-Gutke, Thejavathi; Hoefner, Georg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 852 – 880;,
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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Formula: C5H6N2O

Intermediate 80: step a (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifiuoromethyl)benzyl)quinoiine (Intermediate 12: step d, 3.0 g, 6,97 mmol) was added THF (40 ml) and the solution was cooled to -70 C. K-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1- methyl-lH-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C bath. After 35 minutes the reaction mixture was quenched with aqueous NH4CI solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5 x 50 mL. The combined organics were washed with brine, dried over Na2S04, filtered and concentrated to dryness to give the title compound.

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; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; 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.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7757-21-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7757-21-3 name is (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2,4-Dichloro-benzylamine (47.3mg 0.269mmol) and 3,4-diraethoxy-3- cyiclobutene-l,2-dione (38.2mg, 0.269mmol) were combined in MeOH (2 ml) and water 104 (2ml) and stirred for 2h. C-(lH-benzoimidazol-2-yl)-methylamine HCI (59.4 mg, 0.269mmol) and sat. aHC( (lml) was added in situ. The mixture was stirred at room temperature overnight. After the mixture was extracted with ethyl acetate, washed with brine, concentrated under vacuum and purified via flash column chromatography to yield 3- [(lH-Benzoiniidazol-2-ylmemyl)-amino]-4-(2,4-dicUoro-benzylam dione(1769). LC/MS: (ESI) (M l i s 402.5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2625-49-2, name is 2-(1-Methyl-1H-imidazol-4-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 2625-49-2, COA of Formula: C6H8N2O2

EXAMPLE 53A {4-[4-(1-Methylimidazol-4-yl)-3-keto-1-butynyl]-2-phenylbenzoyl}-methionine methyl ester To a solution of 1-methyl-4-imidazoleacetic acid (5 mmol) in methylene chloride at 0 C. is added oxalyl chloride (6 mmol) and DMF (0.05 mmol). After 30 minute, the solvent is evaporated in vacuo. The residue is redissolved in dichloromethane, followed by the addition of the resultant acetylene from Example 47A (5 mmol), triethylamine (10 mmol), and copper(I) iodide (1 mmol). The reaction is stirred at 25 C. until TLC analysis indicates no starting material is left in the reaction mixture. The reaction is diluted with ether, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified by column chromatography on silica gel to give the title compound.

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; University of Pittsburgh; US6310095; (2001); B1;; ; Patent; University of Pittsburgh; US2002/193596; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53981-69-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 53981-69-4 name is 1-(1H-Imidazol-2-yl)ethanone, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To an ice coled solution of 1-(1H-imidazol-2-yl)ethanone (2.0 g) in MeOH (36 mL) was added NaBH4 (0.69 g). After stirring for 30 minutes at 0C, the reaction mixture was concentrated in vacuo. The residue was purified with amino-type silica gel column chromatography (0- 10 % MeOH in CHCb) to give the title compound (lntermediate-3, 1.9g, 96 % yield) as colorless solid. -NMR data of Intermediate -3 is shown in Table 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Imidazol-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; TAKASHIMA, Hajime; SASAKI, Toru; TANAKA, Nozomi; OTAKE, Norikazu; TSURUTA, Risa; YAMADA, Yousuke; MATSUDA, Yohei; OGATA, Yuya; (346 pag.)WO2018/216822; (2018); 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. 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

a) A mixture of potassium carbonate (832 mg, 6.02 mmol), 2-methyl-5-(trifluoromethyl)-1H-imidazole (450 mg, 3.00 mmol) and ethyl 2-bromopropanoate (0.43 mL, 3.3 mmol) in dimethylformamide:tetrahydrofuran (2 mL:4 mL) was heated at 50 C. for 7 h with stirring and then at room temperature overnight. Most of the tetrahydrofuran was removed by gently blowing nitrogen over the reaction mixture. Ethyl acetate and water were then added and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 17-50% ethyl acetate in hexanes) to afford the desired product (697 mg, 2.79 mmol, 93%).

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; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem