Category: imidazoles-derivatives

Reference of 334893-99-1, The chemical industry reduces the impact on the environment during synthesis 334893-99-1, name is (5-Chloro-1-methyl-1H-imidazol-2-yl)methanol, I believe this compound will play a more active role in future production and life.

A Dess-Martin reagent (1.04 g, 2.46 mmol) was added to a solution of (5-chloro-1-methyl-1H-imidazol-2-yl)methanol (0.300 g, 2.05 mmol) in dichloromethane (20.0 mL) at 0 C. The reaction liquid was stirred at room temperature for 4 hours. The reaction liquid was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane/ethyl acetate) to obtain 5-chloro-1-methyl-1H-imidazole-2-carbaldehyde (0.289 g, 2.00 mmol, 98%) as a white solid. (0157) 1H-NMR (400 MHz, CDCl3) delta: 3.97 (3H, s), 7.24 (1H, s), 9.70 (1H, s).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (5-Chloro-1-methyl-1H-imidazol-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Toray Industries, Inc.; Osada, Yuji; Izumimoto, Naoki; Morita, Yasuhiro; Udagawa, Shuji; Iseki, Katsuhiko; Miyoshi, Tomoya; Iwano, Shunsuke; (38 pag.)US2018/72701; (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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-1,2-dimethyl-1H-imidazole

To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

According to the analysis of related databases, 24134-09-6, the application of this compound in the production field has become more and more popular.

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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); 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. 4499-07-4, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride, A new synthetic method of this compound is introduced below., Product Details of 4499-07-4

To a solution of benzimidazole ethylene amine dihydrochloride (100 mg, 0.43 mmol), 3,4-dimethylphenoxyacetic acid (77 mg, 0.43 mmol), and BOP reagent (190 mg, 0.43 mmol) in acetonitrile (5 mL) was added triethylamine (0.23 mL, 1.72 mmol). After stirring at room temperature overnight, the solvent was removed under vacuum. The residue was taken up with water and saturated sodium bicarbonate (20 mL), extracted with dichloromethane (30 mL x 2), dried and removed the solvent. The crude mixture was purified by using Gilson HPLC to give white solid 5 as a TFA salt (170 mg) at 93 % yield. MUX LC/MS (10-99%) M+1/Z 324.163 retention time 2.62 min ; 1H NMR (DMSO) 8 2.12 (s, 3H), 8 2.15 (s, 3H), 8 2.99 (t, 2H, J = 5.88 Hz), 8 3.59 (m, 2H), 8 4.40 (s, 2H), 8 6.64 (dd, 1H, J = 2 Hz, 6.5 Hz), 8 6.75 (d, 1H, J = 1.8 Hz), 8 6.98 (8, 1H, J = 6.6 Hz), 8 7.12 (m, 2H), 7.40 (d, 1H, J = 5.76 Hz), 7.53 (m, 1H), 8.30 (t, 1H, J = 4.56 Hz), 12.24 (s, 1H) ; 13C NMR (DMSO) 8 18.4, 8 19. 57, 8 28.58, 8 36.74, 8 67.07, 8 110.8, 8 111.58, 8 116.13, 8 118.12, 8 120.86, 8 121.52, 8 128. 70, 8 130.12, 8 134.21, 8 137.25, 8 143. 24, 8 152. 74, 8 155.73, 8 167. 85.

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; VERTEX PHARMACEUTICALS, INCORPORATED; WO2005/42497; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 5-bromo-1-methyl-imidazole (18.8 g, 117 mmol) in dichloromethane (50 mL) was added dropwise ethylmagnesium bromide (3 M in Et2O, 38.9 mL, 117 mmol). After stirring at room temperature for 30 min, the reaction mixture was cooled down to 0C with an ice-brine bath and N-methoxy-N-methylthiophene-3-carboxamide (20.0 g, 117 mmol) was added dropwise. The mixture was stirred for 5.5h at room temperature. The mixture was worked-up by addition of water (400 mL), then acidified with aq. HCI (1 M) until pH = 7. After extraction with dichloromethane (3 x 100 mL), the organic layers were washed with water (2 x 100 mL) then dried over MgSO4 and concentrated in vacuo. Purification of the residue on silica gel afforded (1-methyl-1H-imidazol-5-yl)(2-thienyl)methanone [10.2 g, yield 36% ; HPLC/MS : m/z = 193 (M+H) ; logP(HcooH) = 0.52].

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; BAYER CROPSCIENCE SA; WO2009/130193; (2009); 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole

The compound of formula I (0.62 g, 1 eq) was added to acetonitrile (10 ml) and stirred well. KOH (0.14 g, 1.1 eq) was added slowly, stirred for about 10 minutes, The title compound of Example 10 was added (II, R = COOCH3) (0.5 g, 1 eq) was slowly added, and after stirring for 3-4 hours, TLC After the reaction was complete, 50% ethanol (30 mL) was added directly, The reaction was refluxed for 6 hours. After the TLC test reaction was complete, the organic solvent was recovered under reduced pressure, The remaining solution was added dropwise with hydrochloric acid (1: 1) to pH neutral. There are solid precipitation, filtration, washing, extraction of telmisartan crude, Recrystallization of telmisartan (yield 75.1%), liquid purity greater than 98%.

According to the analysis of related databases, 152628-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Specialization Pharmaceutical Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Wu Mingjun; Li Jianfeng; Chen Weiming; Tian Guanghui; Zhu Fuqiang; Suo Jin; Shen Jingshan; (14 pag.)CN104768936; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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. HPLC of Formula: C7H7N3

Example 38 N-(1H-benzo[d]imidazol-5-yl)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxopyri din-1(2H)-yl)-3-phenylpropanamide 38 Compound 8i (80 mg, 181.86 mumol), 1H-benzo[d]imidazol-5-amine 38a (24.22 mg, 181.86 mumol, prepared by a known method disclosed in “”) and N,N-diisopropylethylamine (70.51 mg, 545.59 mumol) were added to 10 mL of tetrahydrofuran, followed by addition of a solution of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide in ethyl acetate (50%, 231.34 mg, 363.73 mumol). After completion of the addition, the reaction solution was warmed up to 50C, and stirred for 1.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was added with 25 mL of saturated sodium bicarbonate solution, and extracted with ethyl acetate (50 mL*2). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by the silica gel column with elution system A to obtain the title compound 38 (75 mg, yield: 74.3%). MS m/z (ESI): 555.5 [M+1] 1H NMR (400 MHz, DMSO-d6) delta 10.84 (s, 1H), 9.05 (s, 1H), 9.14 (s, 1H), 8.27 (s, 1H), 7.79-7.77 (d, 1H), 7.72-7.69 (d, 1H), 7.59-7.52 (m, 2H), 7.41 (s, 1H), 7.34 (s, 1H), 7.30-7.24 (m, 4H), 7.19-7.17 (m, 1H), 6.30 (s, 1H), 6.03-5.99 (m, 1H), 3.52-3.50 (m, 4H), 3.48-3.44 (m, 1H), 2.85-2.75 (m, 2H), 1.25-1.18 (m, 3H).

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

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-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 22884-10-2, Computed Properties of C5H6N2O2

A suspension of imidazol-1-ylacetic acid, compound of formula 2 (50g, 0. 396mol) and phosphorous acid (48.7g, 0. 594mol) in sulfolan (180ml) was heated to 75 C for 30 min. The mixture was cooled to 35-40 C and phosphorous trichloride (117ml, 1. 346mol) was gradually introduced while maintaining the temperature between 35-45 C. The mixture was heated to 63-67 C for 3 hours, whereby white solid results. It was then cooled to 0- 5’C and quenched by slow addition of water (500ml) at 0-5 C over a period of 1 hour. The resulting clear solution was heated at 100 C for 3 hours, cooled to ambient temperature and charcoalized. Acetone was added to the charcoalized solution. The mixture was then stirred for 4 hours at 20-25 C and the crystallized product was filtered, washed sequentially with chilled water, acetone and dried to obtain zoledronic acid.

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

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2005/66188; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39021-62-0, These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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.

A mixture of 3-methyl-3H-imidazole-4-carbaldehyde (1.40 g, 12.7 mmol), (R)-(+)-2- methyl-2-propanesulfinamide (2.36 g, 19.1 mmol) and titanium (IV) isopropoxide (11.2 mL, 38.1 mmol) in TEtaF (10 mL) was warmed at reflux for 18 hours. The mixture was cooled to room temperature, and diluted with ether (100 mL) and water (6 mL). The mixture was stirred for 10 minutes and then dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes, and concentrated to afford 2-methyl-propane-2- sulfinic acid [l-(3-methyl-3H-imidazol-4-yl)-prop-(£)-ylidene] -amide as a yellow solid.

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; DISALVO, Darren; FANDRICK, Daniel Robert; HARCKEN, Christian; KUZMICH, Daniel; LEE, Thomas Wai-Ho; LIU, Pingrong; LORD, John; MAO, Can; NEU, Jochen; RAUDENBUSH, Brian Christopher; RAZAVI, Hossein; REEVES, Jonathan Timothy; SONG, Jinhua, J.; SWINAMER, Alan, David; TAN, Zhulin; WO2010/36632; (2010); 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

c) 1.00 g (2.68 mmol) 6-bromo-2-iodo-dibenzofuran, 1.75 g (5.36 mmol) caesium carbonate, 130 mg (0.67 mmol) copper(l) iodide and 150 mg (1.34 mmol) L-proline are added to 670 mg (3.22 mmol) 5H-benzimidazo[1 ,2-a]benzimidazole in 20 ml DMSO under nitrogen. The reaction mixture is stirred for 18 h at 100 C and filtered. THF and toluene are added to the organic phase and the organic phase is washed with water. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product can be used without further purification in step d) (yield = 650 mg (78 %)).1H NMR (400 MHz, CDCI3): delta 8.66 (d, J = 2.2 Hz, 1 H), 8.13-8.19 (m, 2H), 7.96-8.07 (m, 3H), 7.66-7.78 (m, 3H), 7.25-7.45 (m, 5H).

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 28890-99-5.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-22-5, name is 6-Aminobenzimidazole, 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 934-22-5, Computed Properties of C7H7N3

2,3-Dibromo-6-hydroxy-5-methoxybenzaldehyde (0.1 g, 0.32 mmol), 5-Aminobenzimidazole (0.03 g, 0.21 mmol), and isoamyl alcohol (2 mL) were stirred at room temperature under N2. Acetic acid (0.07 mL) was added drop-wise, and the mixture was refluxed overnight. The reaction mixture was filtered, washed with CH2Cl2, MeOH, and dried to yield 26 (0.06 g, 0.14 mmol, 65.4%) as an orange powder. 1H NMR (DMSO, 300 MHz) delta 15.54 (s, 1H), 9.20 (s, 1H), 8.34 (s, 1H), 7.76-7.68 (m, 2H), 7.43 (s, 1H), 7.38 (s, 1H), 3.86 (s, 3H); 13C NMR (DMSO, 700 MHz) delta 162.30, 154.74, 149.45, 144.27, 140.84, 120.42, 118.82, 118.46, 117.60, 117.43, 117.10, 113.95, 112.87, 56.78. Rf=0.48 (CH2Cl2/MeOH 9:1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Shim, Hyun Jae; Yang, Hye Ran; Kim, Han Ie; Kang, Shin-Ae; No, Kyoung Tai; Jung, Young Hoon; Lee, Seung-Taek; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4659 – 4663;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem