Category: imidazoles-derivatives

Some common heterocyclic compound, 17286-47-4, name is 2-(1H-Imidazol-2-yl)ethanamine dihydrochloride, molecular formula is C5H11Cl2N3, 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. Formula: C5H11Cl2N3

To a mixture of 3 -chloro-2-(4-fluorophenyl)quinoxaline-6-carbonyl chloride ( 1.03 g, 3.21 mmol, prepared according to Example 44, Route 1, Step 3) in N,N-dimethylacetamide (45 mL) was added 2-(lH-imidazol-2-yl)ethanamine dihydrochloride (709 mg, 3.85 mmol) and TEA (2.24 mL, 16.1 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction was then poured into saturated sodium bicarbonate (50 mL). Water (50 mL) and ethyl acetate (200 mL) were added. The layers were separated and the aquous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (5 x 50 mL), dried, filtered and concentrated in vacuo. Silica gel chromatography gave N-(2-( 1 H-imidazol-2-yl)ethyl)-3 -chloro-2-(4-fluorophenyl)quinoxaline-6- carboxamide (541 mg, 42%). LCMS (ESI+): m/z = 396.1 (M+H). H NMR (400 MHz, OMSO-d6) delta 11.86 (bs, 1H), 9.06 (t, J= 5.6 Hz, 1 H), 8.55 (d, J= 1.6 Hz, 1 H), 8.30 (dd, J= 8.8, 1.6 Hz, 1 H), 8.27 (d, J= 8.8 Hz, 1 H), 7.96-7.93 (m, 2 H), 7.45-7.40 (m, 2 H), 6.92 (bs, 2 H), 3.68-3.62 (m, 2 H), 2.97-2.93 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17286-47-4, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; GIGSTAD, Kenneth, M.; CARDIN, David, P.; HIRAYAMA, Takaharu; HIROSE, Masaaki; HU, Yongbo; KAKEI, Hiroyuki; LEE, Hong, Myung; MOTOYAJI, Takashi; NII, Noriyuki; SHI, Zhan; VYSKOCIL, Stepan; WATANABE, Hiroyuki; WO2015/161142; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, molecular formula is C8H12N2O2, 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. category: imidazoles-derivatives

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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 172499-76-2, its application will become more common.

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. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 2-Phenyl-1H-imidazole-4-carbaldehyde

COMPOUND 12.1.63: 1-{4-[(DIETHYLAMINO)CARBONYL]PHENYL}-6- METHOXY-2-[(2-PHENYL-lH-IMIDAZOL-5-YL) METHYLl-1. 2*3. 4- TETRAHYDROISOQUINOLIN-7-YL DIMETHYLSULFAMATE; INTERMEDIATE 8.3. 1 (53 mg, 0.11 mmol) and2-phenylimidazole-4-carbaldehyde (48 mg, 0. 28 mmol) were dissolved in 1, 2-dichloroethane (5 mL) and stirred for 10 min at room temperature. Sodium triacetoxyborohydride (120 mg, 0.55 mmol) was added and the mixture was stirred for 18 h. Tosylhydrazine resin (0.37 g, 1.5 mmol/g) and DCM (5 mL) were added and the mixture was stirred for another 2 h. The resin was filtered off and washed twice with DCM. The filtrate was washed with 1 M aqueous sodium hydroxide solution, water, and brine, dried, and evaporated. Flash chromatography of the residue yielded the desired product (36 mg, 0.06 mmol, 53 %). ‘H NMR (500 MHz, DMSO): 1.02, 1.15 (2 brs, 6H), 2.72 (s, 6H), 3.04 (m, 2H), 3.18 (m, 3H), 3.40 (m, 3H), 3. 82 (s, 3H), 5. 38 (s, 1H), 6.42 (s, 1H), 7.18 (s, 1H), 7.40 (m, 4H), 7. 58 (m, 4H), 7.59 (s, 1H), 7.98 (d, J 8.0 Hz, 2H). (+) LRESIMS mlz 618 [M+H] +.

The synthetic route of 68282-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 827-43-0, These common heterocyclic compound, 827-43-0, name is 4-Methyl-2-phenyl-1H-imidazole, 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: A mixture of bicyclic olefin 2a (0.2083 mmol, 1.75 equiv),2-phenylimidazole (0.1191 mmol, 1.0 equiv), [RhCl2Cp*]2(0.0029 mmol, 2.5 mol%), and Cu(OAc)2·H2O (0.1338mmol, 1.5 equiv) were weighed in a Schlenk tube anddegassed for 10 min. Anhydrous MeCN (2 mL) was added,and the reaction mixture was purged with argon and allowedto stir at 80 C for 12 h. The solvent was evaporated invacuo, and the residue was purified with columnchromatography (silica gel, 100-200 mesh) using anEtOAc-hexane mixture. Mono- and biscyclopentenylfunctionalizedaza heteroaromatics were obtained in 48%and 39% yields, respectively.

Statistics shows that 4-Methyl-2-phenyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 827-43-0.

Reference:
Article; Prakash, Praveen; Aparna; Jijy; Santhini; Varughese, Sunil; Radhakrishnan; Synlett; vol. 25; 2; (2014); p. 275 – 279;,
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. 31722-49-3, name is 1H-Imidazole-2-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C4H3N3

l,8-Diazabicyclo[5.4.0]undec-7-ene (7.28 mL, 48.75 mmol) was added to a stirred solution of (R)-tert-butyl-4-(5-bromo-2-fluorophenyl)-4-methyl-l,2,3-oxathiazolidine- 3-carboxylate 2,2-dioxide (10 g, 24.4 mmol) and lH-imidazole-2-carbonitrile (2.61 g, 28.03 mmol) in acetonitrile (80 mL). The mixture was stirred at 90 C for 18 hours and then diluted with HCl (1 M) and extracted with DCM. The organic layer was separated, dried (Na2S04), filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield (R)-tert-buty [ 1 -(5-bromo-2-fluorophenyl)-2-(2-cyano- lH-imidazol- 1 -yl)- 1 -methylethyljcarbamate (10 g, 97 % yield) as a sticky solid.

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; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); 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. 1262035-61-9, name is 5-Bromo-1-cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 1262035-61-9

A microwave vial was charged with 5-bromo-1-cyclopropyl-1H-imidazole (40 mg, 0.21 mmol), 3-methoxy-1-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)- 1H-pyrazole-4-carboxamide (75 mg, 0.21 mmol), cesium carbonate (137 mg, 0.42 mmol) and Pd(dppf) G3 (20 mg, 0.02 mmol). Dioxane (1.5 mL) and water (75 muL) were added. The vial was purged with N2, sealed and irradiated in a biotage microwave at 120 C for 1 h. After this time he volatiles were removed under reduced pressure and the resulting black residue was taken up in DMSO and subjected to prep-HPLC (using a Sunfire Prep C18 OBD, 5mum 30x50mm column and using 95% water/5% MeCN (initial conditions) to 50% water/50% MeCN over 20 minutes in 0.1% TFA as the mobile phase at a flow rate of 50 mL/min). The fractions containing product were combined, evaporated to dryness and the resulting residue was dissolved in DCM (20 mL) and washed with satd. NaHCO3 (10 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated to give the title compound (28 mg, 40%) as a white solid. 1H NMR (400 MHz, CDCl3) d ppm 8.53 (s, 1H), 8.01 (t, J=1.8 Hz, 1H), 7.79 (s, 1H), 7.57 (d, J=0.8 Hz, 1H), 7.46 – 7.41 (m, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.25 (td, J=1.4, 7.8 Hz, 1H), 7.11 (d, J=1.3 Hz, 1H), 4.09 (s, 3H), 3.78 (s, 3H), 3.42 (tt, J=3.7, 7.2 Hz, 1H), 1.06 – 0.98 (m, 2H), 0.90 – 0.82 (m, 2H). MS (ESI): 338.1 [M + H]+.v

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; BIOGEN MA INC.; GONZALEZ LOPEZ DE TURISO, Felix; XIN, Zhili; HIMMELBAUER, Martin; JONES, John, H.; (147 pag.)WO2020/36949; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2034-22-2, 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. 2034-22-2 name is 2,4,5-Tribromoimidazole, 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.

A dried 500 mL round bottom flask was charged with 2,4,5-tribromoimidazole (5 1, 20.0 g, 65.6 mmol) and anhydrous DMF (100 mL), and the resulting solution was cooled to 0C. To this cold solution was added NaH (60% in mineral oil, 2.80 g, 70.0 mmol) portionwise with gas evolution under control and an internal temperature maintained below l0C. After addition, the cold bath was removed and the resulting mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was cooled back to 0C, and SEMC1 (12.2 mL, 69.5 mmol) was added to the reaction via syringe pump over 30 minutes. The reaction was stirred at 0C for an additional 30 minutes and at room temperature for another 30 minutes. The mixture was partitioned between EtOAc (150 mL) and water (300 mL), the organic phase was washed with dilute aqueous NaCl (5percent w/w) twice, then brine (100 mL), dried (Na2S04), and concentrated. The crude material was re-crystallized from hot petroleum ether (30 mL) and the solids were harvested from the mother liquor at 0C. The product was washed with cold petroleum ether (30 mL) and dried under vacuum to afford 2,4,5-tribromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole (5_2). 1H MR (400 MHz, CDCh) d 5.31 (s, 2H), 3.59 (t, J= 7.2 Hz, 2H), 0.92 (t, J= 7.2 Hz, 2H), -0.01 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4,5-Tribromoimidazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; CLAUSEN, Dane James; YU, Wensheng; KELLY, Joseph, M.; KIM, Hyunjin, M.; KOZLOWSKI, Joseph, A.; (202 pag.)WO2020/28150; (2020); A1;,
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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-imidazole-2(3H)-thione

General procedure: A mixture of tosylhydrazone 1 (1 mmol), thiol 2 (1.5 mmol, 1.5 equiv), K2CO3 (2.5 mmol, 2.5 equiv) in toluene (4.0 mL) was stirred at 100 C for 24h under Argon. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature. After adding CH2Cl2 (10 mL), the organic phase was washed with saturated NaHCO3, brine and dried with Na2SO4, and concentrated under reduced vacuum. The residue was then purified by flash chromatography on silica gel to afford product 3.

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Garcia-Carrillo, Mario Alfredo; Guzman, Angel; Diaz, Eduardo; Tetrahedron Letters; vol. 58; 20; (2017); p. 1952 – 1956;,
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. 930-62-1, name is 2,4-Dimethylimidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H8N2

Copper oxide (0.045 g, 0.316 mmol), 4,7-bis(methyloxy)-1 ,10-phenanthroline (0.228 g, 0.948 mmol), polyethylene glycol (1.248 g, 11.76 mmol), cesium carbonate (2.88 g, 8.84 mmol), 2,4-dimethyl-1 H-imidazole (0.729 g, 7.58 mmol) and 1 ,1-dimethylethyl3-chloro-5-iodobenzoate (D53, 2.139 g, 6.32 mmol) were transferred into a dried round-bottomed flask vial and capped with a rubber septum. The flask was then evacuated and backfilled with argon – this process was repeated several times. Butyronitrile (3.12 ml.) was then added and the mixture was stirred at 80 0C overnight during which time the reaction had evaporated to dryness. Further butyronitrile (3.12 ml.) was added and the mixture stirred at 80 0C over the weekend.The mixture was diluted with dichloromethane and then filtered through celite. The filtrate was concentrated in vacuo and the resulting crude material (2.8 g) was purified by flash chromatography with a gradient of 0 – 100% ethyl acetate in hexane to afford the title compound as a white solid.LC/MS (ES+ve): [M+H]+ at m/z 307, 309 (C16H19CIN2O2 requires [M+H]+ at m/z 307, 309)

According to the analysis of related databases, 930-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/819; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

4-lodo-1tf-imidazole (2.8g, 14.6mmol) and trityl chloride (5.Og, 20.5mmol) were dissolved in lambda/,lambda/-dimethylacetamide (45mL). The solution was cooled to 0″C and triethylamine (4mL, 29.2mmol) added slowly. The reaction mixture was slowly warmed to room temperature. After 48 hours the solution was poured to water(15OmL). The solid was filtered, washed with water, hexane and dried to give a white solid (5.7g) with a yield of 90%. The product was pure enough for the next step reaction 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; S BIO PTE LTD; WO2009/93981; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem