Imidazoles-derivatives

Related Products of 6478-73-5, These common heterocyclic compound, 6478-73-5, name is 5,6-Dichloro-1H-benzo[d]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.

Example 23[0164] Preparation of (4aR, 7R, 8S,8aR) 5, 6-dichloro-1- (8-fluoro-2-phenyl-hexahydro- pyrano [3,2-d] [1,3]dioxin-7-yl)-1 H-benzoimidazole. EMI54.1[0165] To a solution of (4aR, 7S, 8R, 8aR) trifluoromethanesulfonic acid 8-fluoro-2- phenyl-hexahydropyrano [3,2-d] [1, 3] dioxin-7-yl ester (47.2 mg, 0.12 mmol), prepared according to earlier procedures, in 5 mL of DMSO was added 5, 6-dichloro-1H- benzoimidazole (524 mg, 2.8 mmol) and NaH (67 mg, 2.8 mmol). The mixture was stirred at 70 C overnight. After aqueous work-up and extraction with Et2O, The combined organic fractions were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography to give (4aR, 7R, 8S, 8aR) 5, 6-dichloro-1- (8-fluoro-2-phenyl-hexahydro-pyrano [3,2-d] [1,3] dioxin- 7-yl)-1 H-benzoimidazole. [0166] Yield: 29. 4 mg (58%); Rf= 0. 5 (1: 1 EtOAc-hexane). 1H NMR (CDCl3, 300 MHz) 6 3.61-3. 75 (1H, ddd), 3.80 (1H, dt), 4.14 (1H, m), 4.44-4. 51 (3H, m), 4.66 (1H, m), 5.05-5. 21 (1H, d), 5.49 (1H, s), 7.26-7. 44 (5H, m), 7.60 (1H, s), 7.97 (1H, s), 8.51 (1H, s).

Statistics shows that 5,6-Dichloro-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 6478-73-5.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; WO2005/49582; (2005); 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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 137049-00-4

The product from Example 225C (0.044 g, 0.15 mmol), 1- methyl-1H-imidazole-4-sulfonyl chloride (0.033 g, 0.180 mmol) and triethylamine (0.042 mL, 0.30 mmol) were combined in dichloromethane (0.75 mL), heated at 60 C for 2 hours and concentrated. Purification by chromatography (silica gel, 0-3% methanol in dichloromethane) afforded the title compound (0.038 g, 56%). 1H NMR (300 MHz, DMSO-d6) delta 10.21 (s, 1 H) 7.84 (d, J=1.36 Hz, 1 H) 7.75 – 7.78 (m, 2 H) 7.48 (dd, J=9.49, 2.71 Hz, 1 H) 7.25 – 7.35 (m, 2 H) 7.21 (d, J=2.71 Hz, 1 H) 7.09 (dd, J=8.82, 2.71 Hz, 1 H) 7.03 (t, J=7.46 Hz, 1 H) 6.89 (d, J=8.82 Hz, 1 H) 6.83 (d, J=7.80 Hz, 2 H) 6.37 (d, J=9.49 Hz, 1 H) 3.67 (s, 3 H) 3.43 (s, 3 H). MS (ESI+) m/z 437 (M+H)+.

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI)COMPANY, LTD.; HUBBARD, Robert Dale; MCDANIEL, Keith F.; PARK, Chang Hoon; PRATT, John K.; SOLTWEDEL, Todd; SUN, Chaohong; WANG, Le; WENDT, Michael D; WO2013/185284; (2013); 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 1003-21-0 as follows. Recommanded Product: 5-Bromo-1-methyl-1H-imidazole

To a solution of 153.3 (2.5g, O.76mmol, 1.Oeq) and5-bromo-1-methyl-1H-imidazole (1.5g, O.92mmol, 1.2eq) in a mixture of 1,2-dimethoxyethane (2OmL) and water (5mL), sodium carbonate (2.4g, 2.3mmol, 3.Oeq) was added. Reaction mixturewas degassed with argon for 15mm. Then [1,1?-Bi s(diphenylphosphino)ferrocene]di chloropalladium(II) complex with CH2C12 (0. 9g, 0. O7mmol, O.leq) was added and again degassed for 5mm. Reaction mixture was stirred at 115 C for 2h. After completion of the reaction, the reaction mixture was transferred into water and extracted with ethyl acetate. Organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain crude product. This was purified by column chromatography using 2% MeOH in CH2C12 to obtain pure 212.1 (1.3g, 60.50%). MS(ES): m/z 281.57 [M+H].

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); 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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 22884-10-2

Examples; CRYSTAL FORMS OF ZOLEDRONIC ACID (ZLD-Ac); Preparation of ZLD-AC crystal form I; General procedure for the preparation of ZLD-AC crystal form I starting from 1- Imidazoleacetic acid (IAA), Phosphorous acid (H3PO3) and Phosphorous oxychloride (POC13) (Examples 1-9, see Table 1) :; A cylindrical reactor equipped with a mechanical stirrer, a thermometer, a reflux condenser and a dropping funnel, is loaded with 1-IMIDAZOLEACETIC acid (IAA), Phosphorous acid and a diluent (Toluene/Chlorobenzene/PEG-400/Silicon oil). The obtained suspension is heated to 75C-80C and Phosphorous oxychloride is added drop- wise. The reaction mixture is then heated to 75C-100C for 1-34 hours. Then water is added at 80C-100C. The mixture is stirred vigorously for about 15 minutes. [In some cases, when Silicon oil is used as a diluent, there is a need to add Toluene in order to improve the separation between the oily phase and the aqueous phase]. Then the phases are separated. The aqueous phase is put in a clean reactor and heated to 95C-100C for 13.5-19 hours. Then it is cooled to 5C and absolute Ethanol is added to obtain a precipitate after stirring at 5C for 2.5-4 hours [In some cases a precipitate of Zoledronic acid is obtained without adding absolute Ethanol as an anti-solvent]. The white product is then filtered, washed with absolute Ethanol and dried in a vacuum oven at 50C for 17-24 hours to obtain Zoledronic acid crystal form I (LOD BY TGA=6. 3%-9. 3%).; ZLD HPLC METHOD: COLUMN: PHENOMENEX PHENYL-HEXYL 5UM, 250X4.6MM MOBILE PHASE: 40MM OCTANSULFONIC ACID SODIUM SALT IN 1% HCLO4, 0.2% H3PO4 : METHANOL (85:15) DETECTION: 220NM STABILITY WAS MEASURED VERSUS THE PRESENCE OF FORM II. P THE STABILITY DATA FOR EXAMPLE 4 IN THE TABLE ABOVE IS:

According to the analysis of related databases, 22884-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/5447; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14700-62-0, name is 2-Benzyl-1H-imidazole, 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 14700-62-0, Recommanded Product: 2-Benzyl-1H-imidazole

a) N,N-dimethylformamide (200 ml) was stirred at room temperature under nitrogen and a dispersion sodium hydride 50% in mineral oil (0.113 mol) was added portionwise. 2-Phenylmethyl-1H-imidazole (0.075 mol) was added portionwise and the mixture was stirred for 1 hour at room temperature. Ethyl chloroacetate (0.113 mol) dissolved in N,N-dimethylformamide was added dropwise and the mixture was stirred at room temperature for 30 minutes. The mixture was poured into a NaHCO3 solution and extracted with dichloromethane. The organic layer was dried (MgSO4), filtered off and evaporated. The residue was purified on a glass filter over silica gel (eluent: CH2 Cl2 /CH3 OH 95/5). The pure fractions were collected and evaporated, yielding 16 g (93%) of product. A sample (1 g) was crystallized from 2,2′-oxybispropane/acetonitrile, yielding 0.58 g of methyl 2-(phenylmethyl)-1H-imidazole-1-acetate; mp. 70.8 C. (interm. 21). A mixture of intermediate (21) (0.017 mol) in trifluoromethanesulfonic acid (25 ml) was stirred at 140 C. overnight. The mixture was cooled, poured into a K2 CO3 solution/ice water and extracted with dichloromethane/ethanol.

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; Janssen Pharmaceutica N.V.; US5674866; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

0.680 g (10 mmol) of imidazole was weighed and 1.240 g (10 mmol) of p-fluorobenzaldehyde and 1.380 g (10 mmol) of anhydrous potassium carbonate were weighed and dissolved in 25 mL of N, N-dimethylformamide, Thermometer, stirring device 50mL four-necked flask.60 C for 20h, cooled to room temperature, poured into 100mL ice water, a yellow solid precipitated, suction filtered, recrystallized from ethanol, dried at 50 C for 8h under vacuum to give 4-imidazolyl benzaldehyde

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qilu University of Technology; Xu Ting; Duan Hongdong; Bu Juan; (12 pag.)CN107043353; (2017); A;,
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. 71759-89-2, name is 5-Iodo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H3IN2

After dissolving 4-iodo-1H-imidazole (3.0 g, 0.015 mol) and triphenylmethyl chloride (6.0 g, 0.021 mol) in anhydrous N, N-dimethylformamide (50 mL) Deg.] C, triethylamine (7.2 mL, 0.052 mol) was added slowly, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated, and then distilled water (100 mL) was added thereto. After stirring at room temperature for 20 minutes, the solid was filtered The filtrate was washed with distilled water and diethyl ether to give the title compound 60-a (4.4 g, 66%) as a white solid.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rego Kem Bio Between Eonseu Co., Ltd.; Lee Dae-yeon; Chae Sang-eun; Jeong Eun-mi; Yang Eun-hye; Choi Yun-jeong; Jeong Cheol-ung; Shin Ju-hyeon; Kim Yun-gi; Kwon Hyeon-jin; Ryu Jeong-hui; Ban Eun-hye; Kim Yong-ju; Oh Yeong-su; Chae Je-uk; (140 pag.)KR101798840; (2017); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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. name: 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-Iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)Benzamide: 3-Iodo-4-methylbenzoic acid (2.62 g, 10 mmol) was refluxed in soc2 (10 mL) for 5 1 h. The volatile components were removed on a rotavap and the residue was dissolved inbenzene (10 mL), concentrated to dryness on a rotavap and further dried under vacuum. The resulting acyl chloride was added to a solution 3-(4-methyl-IH-imidazol-I-yl)-5- (trifluoromethyl)benzenearnine (2.46 g, 10.2 mmol), N,N-diisopropylethylamine (1.56 g, 12 mmol), and a catalytic amount of DMAP in THF (20 mL). After stirring at rt for 2 h, the reaction10 was quenched with water. EtOAc was added and the layers separated. The combined organic layers were concentrated to dryness and used without purification in next step.

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16681-56-4, name is 2-Bromo-1H-imidazole, 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 16681-56-4, Formula: C3H3BrN2

Intermediate 124 (150 mg, 0.25 mmol), 2-bromoimidazole (46 mg, 0.31 mmol) andsodium carbonate (79 mg, 0.75 mmol) were suspended in 1 ,4-dioxane (3 mL) andwater (0.25 mL). The reaction mixture was degassed with argon (5 minutes), Pd(PPh3)4 (29 mg, 0.025 mmol) was added and the reaction mixture was heated at 110 C for 12 h in a microwave reactor. The cooled reaction mixture was filtered through celite, washed with EtOAc, then DCM and the filtrate was evaporated in vacuo. The crudematerial was dissolved in THF (4 mL) and TBAF (1M in THF) (1 mL) and heated to40 C for 2 hours. The reaction mixture was concentrated in vacuo and purified bypreparative chromatography using acidic eluent. The material was retrieved andpurified by preparative chromatography using basic eluent to give 6.2 mg of compound163 (6% yield, pale yellow amorphous solid).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HYND, George; MACLEOD, Calum; MANN, Samuel, Edward; KULAGOWSKI, Janusz, Jozef; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; PONCELET, Virginie, Sophie; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; (290 pag.)WO2019/8011; (2019); 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. 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, A new synthetic method of this compound is introduced below., Product Details of 10364-94-0

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

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; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem