Month: May 2021

Reference of 31250-80-3, 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. 31250-80-3, name is 1-Benzyl-2,4,5-tribromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

The synthetic route of 1-Benzyl-2,4,5-tribromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chelucci, Giorgio; Figus, Susanna; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 191 – 209;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 256518-97-5, 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 256518-97-5 as follows.

Step 5: Under nitrogen protection, 2-chloro-6-iodo-1H-benzimidazole (2.34 g, 8.4 mmol) was added to the reaction vessel.Isopropyl boric acid (0.81 g, 9.2 mmol), tetrakistriphenylphosphine palladium (0.05 g, 0.04 mmol),Potassium carbonate (1.74 g, 12.6 mmol), toluene 60 mL, ethanol 20 mL, and distilled water 20 mL were stirred at 120 C for 3 h.After the end of the reaction, the reaction was quenched with distilled water, extracted with ethyl acetate and dried over MgSO 4The solvent was evaporated under reduced pressure, and then purified by silica gel column chromatography to afford compound 35-5 (1.26 g, 77%).

According to the analysis of related databases, 256518-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (23 pag.)CN109305943; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 67768-61-0,Some common heterocyclic compound, 67768-61-0, name is 1-Cyclohexyl-1H-imidazole, molecular formula is C9H14N2, 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.

2,4,5-tribromo-1-cyclohexyl-1H-imidazole (12.2.). N-bromosuccinamide (1.78 g, 9.99 mmol) dissolved in CHCl3 (4 ml) at 0 C. was added to a 4 ml solution of 12.1 (500 mg, 3.33 mmol) in CHCl3. The mixture was stirred at rt for 17 h, filtered, concentrated, and the crude residue stirred in ether for 30 min. Filtration and concentration gave a crude product which was purified by SiO2 chromatography (10% EtOAc/hexanes) to afford 267 mg (21%) 12.2. MS (ESI) 385.0 (MH+).

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

Reference:
Patent; Glunz, Peter W.; Douty, Brent D.; Martin, Scott W.; Romine, Jeffrey; US2005/75376; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 92807-02-8, A common heterocyclic compound, 92807-02-8, name is Methyl 2-mercapto-1H-benzo[d]imidazole-4-carboxylate, molecular formula is C9H8N2O2S, 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 solution of methyl 2-sulfanyl-1H-benzimidazole-4-carboxylate (prepared as described in WO2003/106430) (1.0g) in DMF (15 mL), were added potassium carbonate (700 mg) and methyl iodide (0.32 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (860 mg) as white powder.

The synthetic route of 92807-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; OTSU, Hironori; EP2746265; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89088-69-7, These common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, 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 solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

Statistics shows that 1-Methyl-1H-imidazol-4-amine hydrochloride is playing an increasingly important role. we look forward to future research findings about 89088-69-7.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 342789-81-5,Some common heterocyclic compound, 342789-81-5, name is 1-Butyl-3-methylimidazolium methanesulfonate, molecular formula is C9H18N2O3S, 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.

5.3-1-Butyl-3-methylimidazolium N-trifluoro-sulfonamidate [BMI.(CF3SO2)2N]A mixture formed by 1,3-dimethyl imidazolium methanesulfonate (BMI.CH3SO3) (4.26 g; 18.2 mmol), lithium N-trifluoro sulfonimidate (5.47 g; 19.1 mmol) and water (10.0 mL) was stirred at room temperature for 45 minutes. The resulting mixture, made up by two phases, was extracted with dichloromethane (3×15 mL). The combined organic extract was washed with water (1×20 mL) and dried with anhydrous sodium carbonate. The solvent was evaporated under vacuum and heated (80 C.), which produced the desired ionic liquid BMI.(CF3SO2)2N (7.33 g. 96% yield).

The synthetic route of 342789-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETROLEO BRASILEIRO S.A. – PETROBRAS; US2008/45723; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, 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. Formula: C9H11N3

Step 2; N3-[4-[2-(Benzimidazol-2-yl)ethyl)aminomethylbenzoyl)-N2-Cbz-L-2,3-diaminopropionic acid on 2-chlorotrityl resin; [Show Image] Shake the resin (Preparation 4, Step 1) (0.8 g, 0.4 mmol) and 2-[2-(aminoethyl)]benzimidazole (3.25 g) in DMF (25 mL) in a sealed vial for 44 hours. Transfer resin to funnel apparatus, and wash the resin with DMF (25 mL x 5) and then CH2Cl2 (20 mL x 5) to give the title resin.

The synthetic route of 2-(1H-Benzo[d]imidazol-2-yl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; EP1135374; (2006); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1008360-84-6, 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. 1008360-84-6 name is 5-Bromo-6-fluoro-1H-benzo[d]imidazole, 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 5-bromo-6-fluoro-1H-benzimidazole (2.2 g, 10.2 mmol) in tetrahydrofuran (40 mL) at 0 degrees C. was added sodium hydride (0.5 g, 12.3 mmol) as a solid in 2 portions. After stirring 30 min. at 0 C., trityl chloride (3.7 g, 13.3 mmol) was added, followed by tetrabutylammonium iodide (catalytic). The reaction was heated at reflux for 1.5 h, then was allowed to cool and was quenched with water. The mixture was extracted with chloroform (3×) and the combined organics were dried over sodium sulfate and concentrated in vacuo. The residue was triturated with hot ethyl acetate and the solid was isolated via filtration and dried under vacuum. This provided the product as a mixture of trityl regioisomers, 5-bromo-6-fluoro-1-(triphenylmethyl)-1H-benzimidazole and 6-bromo-5-fluoro-1-(triphenylmethyl)-1H-benzimidazole.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-6-fluoro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (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. 169770-25-6, name is Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H7N3O4

Methyl l-methyl-4- nitroimidazole-2-carboxylate 40 (3.3 g, 17.8 mmol), dissolved in 1 : 1 MeOH:EtOAc (100 niL), was shaken with hydrogen at 70 psi, for 14 h in presence of Pd/C (400 mg). The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as black oil. The residue was taken up in benzene and concentrated to furnish the amine as black solid, filtered and washed with ether (2.5 g, 88%). The crude amine was dissolved in CH3CN (50 mL) and DIEA (2.3, 18 mmol). A solution of 1- methyl-2-trichloroacetylimidazole 24 (3.6 g, 14.7 mmol) in CH3CN (50 mL) was added to the amine solution at 0 0C. The reaction mixture was allowed to stir for 10 h, solvent was removed and the residue was taken up in MeOH and the product was precipitated by addition Of Et2O to furnish desired compound 41 (2.13 g, 68%). 1H- NMR (DMSO-d6) deltaltheta.1 1 (s, exch, IH, NH), 7.69 (s, IH, Im’-C5H), 7.43 (s, IH, Im- C5H), 7.07 (s, IH, Im-C4H), 3.99 (s, 3H, CH3), 3.97 (s, 3H, CH3), 3.82 (s, 3H, OCH3). 13C-NMR (75 MHz, DMSO-d6) 6159.4 (+, s, CO), 157.2 (+, s, CO), 138.9 (+, s, Im- C2), 137.2 (+, s, Im-C2), 132.4 (+, s, Im-C4), 128.9 (-, d, Im-C4), 127.7 (-, d, Im-C5), 117.3 (-, d, Im-C5), 61.9 (+, t, -OCH2-), 37.6 (-, q, CH3), 35.8 (-, q, CH3), 14.2 (-, q, CH3). EI-HRMS: m/z calcd for C1 1H13N5O3 263.1018; found 263.1016 (M+, 100%), 204.0888 (27%), 182.0573 (27%), 150.0301 (30%), 109.0393 (26%).

The synthetic route of 169770-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF SASKATCHEWAN; WO2007/45096; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 6953-65-7 as follows. category: imidazoles-derivatives

A mixture of (5-Chloro-1 H- benzoimidazol-2-yl)-methanol (3.8 g) suspended in 2 N sodium carbonate (110 mL) was treated with a solution of [KMN04] (4.935 g in 310 mL of water). The resulting mixture was heated to [100 C] for 2 h and then filtered. The filtrate was cooled to room temperature, and the solution was adjusted to acidic pH, via addition of 3 N acetic acid, to afford a precipitate. The solid material was isolated by filtration, washed with water and dried under vacuum to give the title intermediate (2.910 g). This material was used in Step C without further purification.

According to the analysis of related databases, 6953-65-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/22060; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem