Month: September 2021

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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, A new synthetic method of this compound is introduced below., SDS of cas: 6160-65-2

To a stirred solution of 6.8 g (35.0 mmol) of (5) in 150 mL Of CH2Cl2 at RT was added 6.4g (35mmol) of l,l ‘-thiocarbonyldiimidazole. The mixture was stirred at room temperature for 15 minutes and then evaporated under reduced pressure and the residue was passed through a short pad of silica gel, eluting with a gradient of hexane/EtOAc, which gave (5-Isothiocyanato-2-methoxy-phenyl)-methyl-propyl-amine (6) (7.85g, 95%) as a colorless oil.

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; SYNTA PHARMACEUTICALS CORP.; WO2008/57246; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16042-25-4, A common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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 a stirred suspension of 1H-imidazole-2-carboxylic acid (3.00 g, 26.8 mmol) in anh. DCM (45 mL)cooled to 0 C under N2 was added oxalyl chloride (4.5 mL, 53.5 mmol) followed by addition of DMF (2 drops). The reaction was allowed to warm to rt and stir overnight. A further portion of oxalylchloride (1.13 mL, 13.4 mmol) and DMF (1 drop) was added and the reaction stirred for 4 hr.Volatiles were then removed in vacuo and the residual oxalyl chloride was removed by coevaporationwith toluene to afford acid chloride as a colourless solid. The solid was then addedportionwise to conc NH4OH (15 mL) chilled to 0 C. Volatiles were then removed in vacuo.Residual volatiles were coevaporated with toluene to obtain dry material (25: 75 startingmaterial:product). The crude was retreated to the reaction with oxalyl chloride (1.7 mL, 20.1 mmol)using the above procedure. The solid obtained was then washed with water (2 x 20 mL) and driedin vacuo to obtain a tan solid (2.16 g, 73%) that was used without further purification. LCMS (Waters Atlantis: Gradient Method 2): Rt = 1.44 min, 99 A% 254 nm, [M + H]+ = 112.2. 1H NMR(600 MHz, DMSO-d6) delta 12.95 (s, 1H), 7.73 (s, 4H), 7.43 (s, 1H), 7.23 (br s, 1H), 7.04 (br s, 1H).

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; Jarrad; Debnath; Miyamoto; Hansford; Pelingon; Butler; Bains; Karoli; Blaskovich; Eckmann; Cooper; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 353 – 362;,
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. 934-22-5, name is 6-Aminobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 6-Aminobenzimidazole

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1546-79-8, 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. 1546-79-8 name is 2,2,2-Trifluoro-1-(1H-imidazol-1-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.

I -(‘rrifliioroacetyl)iniida ole (37.7 p.L, 331 mueta,iotaomicronIota, 6.00 equiv) was added dropwise to a solution of I2-p ~mutilm 94 (17.7 mg. 55.2 mutauetaomicron, 1 equiv) in ethyl acetate (1.0 mL) at -78 C. The resulting mature was stirred for 50 mm a -78 C. The product mixture was diluted with aqueous hydrochloric acid solution (1 , 200 pL) and then was wai’med to 22 C over 1 h. The warmed product .mixture was diluted with aqueous hydrochloric acid solution (.1 M, 1. mL), The diluted product mixture was extracted with ethyl acetate (3 x 5 mL). The organic layers were combined and the combined organic layers were dried over sodiam sulfate. The dried solution was filtered and the. filtrate was concentrated. The residue obtained was purified by preparative thiii-layered chromatography (elutiog with 40% ether-pentaue) to provide the ester S16 as a white solid (15.0 mg, 65%). Rf~ 0.65 (40% ether-pentane, PAA stains purple) H NMR (500 MHz, CDCU) 5.62 (dd, ./= 17.4, 10.8 Hz, 1 H), 5.12-4.98 (m, 3H), 4,39-4.33 (m, IH), 2.53 (p, J – 7.2 Hz, 1H), 2.38-2.03 (m, 4H), 1.82-L66 (m, 3H), 1.60-1.40 (m, 3H), 1.38 (s, 3H 1 -33 (s, 3H), 1.29-1.13 (m, 2H), 0.99 (d, J = 7.1 Hz, 3H 0.83 (d, J = 7.1 Hz, Ml } 5SF NMR (470 MBzs CD?)?-75.09 (s, 3F). ,3C NMR (151 MHz, CDC ) 216.8, 156.8 (q, / – 42.0 Hz), 145,0, 1 14.8 (q, J~ 286.1 Hz), 1 14.0, 80.1, 66.4, 59.2, 46.0, 45.2, 43.8, 42.7, 36.9, 34.9, 34.5, 30.4, 27.3, 25.3, 183, 15.0, 13,5, 1 1 ,6. HRMS-ESI (m/z): calculated for [C22- FjOjN ]”*’ 439.2067, found 439.2046.

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

Reference:
Patent; YALE UNIVERSITY; HERZON, Seth; MURPHY, Stephen, K.; ZENG, Mingshuo; (194 pag.)WO2018/144717; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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 29 Diethyl imidazole-4,5-dicarboxylate (46) Imidazole-4,5-dicarboxylic acid (7.55 g, 50.0 mmol) is dissolved in absolute ethyl alcohol (120 mL). The solution was cooled in an ice bath to 0 C. and bubbled dry HCl gas for 1 h. Later, the reaction mixture was refluxed at 80 C. for 7 h during which time all the starting material was consumed. The solvent was removed and the residue that obtained was dissolved in dichloromethane (200 mL) and the organic layer was neutralized with triethylamine. The organic layer was washed with cold water (100 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give 5.50 g (52%) of white solid: mp 175-177 C.; 1 H NMR (CDCl3) delta 1.40 (t, 3H), 4.41 (m, 2H), 7.84 (1H, C2 H) and 11.55 (br s, 1H, NH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4,5-dicarboxylic acid, its application will become more common.

Reference:
Patent; ICN Pharmaceuticals, Inc.; US6130326; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15965-31-8,Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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.

Intermediate 27: Methyl {2-[(5-chloro-1 H-imidazol-1-yl)methyl1phenyl)acetateMethyl [2-(bromomethyl)phenyl]acetate (Intermediate 1 , 3 g, 12.34 mmol) and 4-chloro- 1 H-imidazole (Intermediate 26, 3.80 g, 37.0 mmol) were dissolved in dry DMF (100 ml) and stirred at room temperature for 16 hours. After dilution with water the mixture was extracted with DCM, the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (5Og) eluting with a gradient of MeOH in DCM from 0 to 5% to afford the title compound (1.6 g, 6.04 mmol) contaminated with -10% of the regioisomer methyl {2-[(4-chloro-1 H-imidazol- 1-yl)methyl]phenyl}acetate, which was used in the next step without further purification; UPLC/MS Rt=0.50 min; m/z (ES): 265 and 267 [M+H]+ ; 1H NMR (CDCI3) only signals relating to the title compound: delta 3.71 (s, 2H), 3.72 (s, 3H), 5.21 (s, 2H), 6.92 (d, 1 H), 7.05 (d, 1 H), 7.28-7.42 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-1H-imidazole, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; GIANOTTI, Massimo; LESLIE, Colin Philip; STASI, Luigi Piero; WO2010/142652; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 139481-44-0,Some common heterocyclic compound, 139481-44-0, name is Methyl 1-((2′-cyano-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, molecular formula is C25H21N3O3, 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 a 500 mL four-neck flask, 20 g of Compound 1 was added, and while stirring, 100 mL of dimethyl sulfoxide solution in which 10.14 g (3 eq) of hydroxylamine hydrochloride was added was added, and the mixture was heated to 90 DEG C and 30.95 g (6 eq) was added in portions under stirring. Sodium carbonate, after the completion of the reaction for 9-10 hours, after the completion of the reaction, it is allowed to come to room temperature, and 100 mL of water is added to stir the mixture. The solid precipitates, which is cooled down to 0-5C. Stirring is continued for about 1 hour, and the mixture is dried by suction to obtain 15.2 g of compound 2. The yield was 70.4%.

The synthetic route of 139481-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Disha Pharmaceutical Group Co., Ltd.; Fu Kaimin; (7 pag.)CN103242305; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 918321-20-7, These common heterocyclic compound, 918321-20-7, name is Methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate, 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.

In an inertized (N2) reaction vessel at internal temperature 20C and under exclusion of humidity and air, Compound 1 (1.0 eq.) and Compound 2 (1.2 eq.) are reacted in the presence of cesium carbonate (2.4 eq.), tris(dibenzylidenaceton) dipalladium(O) (0.035 eq.) and Xantphos (0.07 eq.) in a mixture of toluene and 1 ,4-dioxane at internal temperature of 99C. After 8 hours, the mixture is cooled to internal temperature of 60C. Subsequently, dimethylformamide (DMF), filter aid (CEFOK) and activated charcoal (EKNS) are added, and the mixture is stirred and cooled to internal temperature of 35 C. The solids are filtered off and washed with a mixture of dimethylformamide and toluene. To the filtrate, which contains the product Compound 3, is introduced at internal temperature of25 C hydrogen chloride gas (CLC) whereupon the HQ salt of Compound 3 crystallizes. The palladium residue mainly remains in solution. After warming to 60 C and cooling to 0C, the solids are filtered using a centrifuge and are washed with a mixture of toluene and dimethylformamide. The damp Compound 3 HC1 salt is charged to a reactor (equipped with pH probe) together with dimethylformamide and is heated to 60C. By adding a 4 wt% of aqueous tripotassium phosphate solution, the pH is adjusted to a pH range of 6.8-7.6 (with a target of pH 7.2) while Compound 3 crystallizes as free base. After cooling to 22C and stirring, the solids are filtered using a centrifuge and are washed with drinking water. The moist solids are dried at 50 C under vacuum to give dry, crude Compound 3. In order to remove residual palladium, dry, crude Compound 3 is dissolved in dimethylformamide at internal temperature of 60C and stirred together with Smopex-234 (commercially available from Johnson Matthey) and activated charcoal for 90 minutes. The solids are filtered off at internal temperature of 60C and are washed with dimethylformamide. To the filtrate are added drinking water and Compound 3 seed crystals. More drinking water is added while Compound 3 crystallizes. After cooling to internal temperature of 20 C, the solids are filtered using a centrifuge and are washed with a mixture of deionized water and dimethylformamide and with deionized water. The moist solids are dried at 50C under vacuum, providing 6-(4-Bromo-2-fluorophenylamino)-7-fluoro-3- methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (Compound 3).

The synthetic route of 918321-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ARRAY BIOPHARMA INC.; KRELL, Christoph, Max; MISUN, Marian; NIEDERER, Daniel, Andreas; PACHINGER, Werner, Heinz; WOLF, Marie-christine; ZIMMERMANN, Daniel; LIU, Weidong; STENGEL, Peter, J.; NICHOLS, Paul; WO2014/63024; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 68282-47-3, 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. 68282-47-3 name is 2-Phenyl-1H-imidazole-4-carbaldehyde, 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 a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.73 g) in ethanol (30 mL) was added 40% methylamine-methanol solution (2.36 g) and the mixture was stirred at 65C for 1 hr. The mixture was allowed to cool to room temperature, sodium borohydride (571 mg) was added and the mixture was stirred for 30 min. 1 mol/L Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with tetrahydrofuran. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0?4:1) and dissolved in methanol (10 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 1.06 g, yield 41%). 1H-NMR(DMSO-d6)delta:2.62(3H,s), 4.33(2H,s), 7.55-7.73(3H,m), 7.83(1H,s), 8.21(2H,br), 9.64(2H,br), 2H not detected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2196459; (2010); 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. 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; The reaction part was charged with ethyl 4- (1-hydroxy-1-methylethyl) -2-propyl-1- {4- [2- (trityltetrazol-5-yl) phenyl] 22 g of 5-carboxylate (Formula 4), 3.1 g of sodium hydroxide and 90 mL of ethanol were added and the mixture was stirred at 20 to 25 C for 4 to 5 hours. When the reaction was completed, the reaction solution was concentrated. To the residue were added 50 mL of ethyl acetate and 50 mL of purified water. The mixture was stirred for 1 hour and then layered. The separated organic layer was washed twice with an aqueous solution containing 30 g of salt and 170 mL of purified water. 1 g of activated carbon and 20 g of anhydrous sodium sulfate were added to the organic layer, followed by stirring for 30 minutes to 1 hour, followed by filtration. The filtrate was concentrated under reduced pressure, and then methanol (65 mL) was added. The mixture was stirred for 3 hours and then filtered to obtain 4- (1-hydroxy-1-methylethyl) 5-yl) phenyl] phenyl} -methylimidazole-5-carboxylate (formula 5) 20.7g (yield 95%, purity 99.98%)

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

Reference:
Patent; DONGBANG FTL CO., LTD; Song, Tae Hong; Jung, Hun Suk; Jang, Do Yeon; Moon, Chung Sun; Jung, Hee Jung; (18 pag.)KR101526249; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem