Month: October 2020

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, 934-22-5

General procedure: [0205] A solution of benzimidazol-5-amine (1 eq.) in DMF (5 ml) was treated with K2CO3 (2.2 eq.) and the respectivealkylhalide (2.2 eq.) and stirred at room temperature for 24 h. The mixture was diluted with water and extracted by meansof ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4, evaporated and the residue waspurified by flash chromatography on silica using a CHCl3/MeOH gradient; Example 20 N,N-Bis((4-methylbenzyl)-1H-benzo[d]imidazol-5-amine The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), 4-methylbenzylbromide (407 mg; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.109 g (32.0%); MS m/z: 342.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): delta 2.23 (s, 6H); 4.57 (s, 4H); 6.66 (br s, 1 H); 6.71 (dd, 1 H, 4J=2.1 Hz, 3J=8.9 Hz); 7.09 (d, 4H, 3J=7.9 Hz); 7.14 (d, 4H, 3J=7.9 Hz); 7.30 (d, 1 H, 3J=8.5 Hz); 7.88 (s, 1 H); 11.88 (br s, 1 H); HPLC (METHOD [A]): rt 17.36 min (98.1%)

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, 6-Aminobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Probiodrug AG; HEISER, Ulrich; RAMSBECK, Daniel; HOFFMANN, Torsten; BOEHME, Livia; (99 pag.)EP2560953; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4.

General procedure: In a 50mL RB, N-H heterocycles (1.0mmol), aryl halide (1mmol), Cu(II)Pc (0.01mmol), NaOH (1.5mmol) and DMSO (2mL) was added. This reaction mixture was stirred to a preheated oil bath at 100C for 8-12h. After completion of the reaction, it was cooled to room temperature and 20mL ethyl acetate was added. It was filtered; solid catalyst was separated and washed with 2¡Á5mL ethyl acetate. The washing and filtrate were combined and washed with water. Ethyl acetate was removed under reduced pressure and product was purified with column chromatography.

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, 1H-Imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yadav, Kumar Karitkey; Narang, Uma; Bhattacharya, Soumee; Chauhan, Shive M.S.; Tetrahedron Letters; vol. 58; 31; (2017); p. 3044 – 3048;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 693-98-1, name is 2-Methyl-1H-imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 693-98-1

General procedure: alpha,beta-unsaturated compound (4.8 mmol) was added dropwise to a well stirred mixture of N-heterocycle substrate (4.0 mmol) in [n-butyl urotropinium]OH (0.108 g, 0.25 mmol) and the reaction mixture was stirred for required time until completion of reaction (TLC). The product was then directly distilled out from the reaction mixture to provide pure Michael adducts (3a-3f and 4a-4f) in high yields.

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, 693-98-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kumar, Sitanshu; Kaur, Amanpreet; Singh, Vasundhara; Synthetic Communications; vol. 49; 2; (2019); p. 193 – 201;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, molecular formula is C8H7N3O2, 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. 1792-40-1

[0182] (1) Benzoyl chloride (32.5 ml) was added dropwise to a mixture of 2-methyl-5-nitrobenzimidazole (12.5 g) and TEA (38.8 ml) in Diglyme (63 ml) at room temperature. The reaction mixture was stirred at 100[deg.] C. for 1 hour. Water was added to the reaction mixture cooled to room temperature and the whole was stirred for 45 minutes. The reaction mixture was extracted with chloroform, the organic layer was washed with water and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained crude crystals were recrystallized from chloroform-n-hexane to obtain 2-(1-benzoyl-1H-5-nitrobenzimidazol-2-yl)-1-phenylvinyl benzoate (29.7 g, 86%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1792-40-1, its application will become more common.

Reference:
Patent; Hirano, Masaaki; Kawaminami, Eiji; Toyoshima, Akira; Moritomo, Hiroyuki; Seki, Norio; Wakayama, Ryutaro; Okada, Minoru; Kusayama, Toshiyuki; US2003/191164; (2003); 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., 152628-02-9

Example 1 Methyl 4′-((1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazol-3′-yl)methyl)biphenyl-2-carboxylate (V) A 1L four-necked glass vessel, fitted with mechanical stirrer, thermometer, dropping funnel, Dean-Stark apparatus, was charged with 1,7′-dimethyl-2′-propyl-1H,3H-2,5′-bibenzo[d]imidazole hydrate (II) (100 g, 310 mmol) and toluene (400 mL), under nitrogen atmosphere. The resulting mixture was heated under stirring to reflux temperature and the water was eliminated by azeotropic distillation, until a semi-solid stirrable residue was obtained. To the residue was added DMA (200 mL) and the mixture was heated to 30-40C until a complete dissolution of the residue. The resulting solution was then cooled at 0-5C, tBuONa (31 g, 322 mmol) and methyl 4′-(bromomethyl)biphenyl-2-carboxylate (IV) (97 g, 318 mmol) were added in portions. The suspension was stirred at room temperature for 2 hrs, and monitored by quantitative TLC (elution with 5% MeOH in EtOAc) until complete conversion. Water (500mL) and toluene (300 mL) were then added and the resulting solution was heated to 80C until a biphasic system was obtained. The phases were separated and the organic phase was washed with water (3 x 50 mL), dried over sodium sulphate and concentrated until a residual volume of 300 mL was reached. The solution was then quickly cooled until crystallization and the so-obtained solid was filtered and washed with toluene (2 x 40 mL). The collected product was dried at 60C under reduced pressure, affording the title compound (145 g) as a white solid. Yield: 88.4%

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; Chemo Iberica, S.A.; EP2305650; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 872-82-2, name is 2-(1H-Imidazol-5-yl)ethanol, 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. 872-82-2

Preparation 32 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-imidazole A solution of 2-(1H-imidazol-4-yl)ethanol (1.24 g, 11.1 mmol) in DMF (10 mL) was treated with imidazole (1.51 g, 22.1 mmol) and TBDPSCl (3.12 mL, 12.2 mmol) and the mixture was stirred at RT for 2 h. The mixture was then poured onto H2O and extracted with AcOEt. The combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt/heptane 0:100 to 100:0) gave the title compound (1.6 g). UPLC-MS: MS 351.2 (M+H+); UPLC rt 1.02 min.

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 872-82-2.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; US2014/57902; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, Name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 152628-02-9, 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.

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

Statistics shows that 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 152628-02-9.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-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 2302-25-2.

Add tetrakis (triphenylphosphine) palladium (0) (500 mg) to a degassed suspension of H-IMIDAZOLE (5.0 g, 34 mmol) and 2-isopropoxyphenyl boronic acid (9.19 g, 51 mmol) in dioxane (250 mL) and 2 M sodium carbonate solution (10.81 g, 102 mmol) at room temperature under nitrogen and heat the mixture at reflux for 21 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (500 mL) and filter through a plug of Celite. Dry the filtrate over sodium sulfate, treat with silica gel (20 g) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate, to afford crude 4- (2- ISOPROPOXYPHENYL)-1H-IMIDAZOLE (5.01 g, 73%) which is used without further purification in the next step.

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, 4-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/19184; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-69-8, Adding some certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8.

To 100 mg (0.36 mmol) of (S)-5-(4-fluoro-3-(trifluoromethyl)phenyl)-6-methyl-3,6-dihydro- 2H-1,3,4-oxadiazin-2-one (Intermediate 75) and 73 mg of 4-trifluoromethyl imidazole (0.54 mmol) dissolved in 2 mL of DMF was added 235 mg of powdered Cs2C03 (0.72 mmol) and the mixture was heated at 80 Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; ELLERMANN, Manuel; GRADL, Stefan, Nikolaus; KOPITZ, Charlotte, Christine; LANGE, Martin; TERSTEEGEN, Adrian; LIENAU, Philip; HEGELE-HARTUNG, Christa; SUeLZLE, Detlev; LEWIS, Timothy, A.; GREULICH, Heidi; WU, Xiaoyun; MEYERSON, Matthew; BURGIN, Alex; (500 pag.)WO2019/25562; (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. 84946-20-3, name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., 84946-20-3

A mixture of 14 2-chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole (2) (261mg, 1mmol) and 133 tert-butyl 3-aminopyrrolidine-1-carboxylate (370muL, 2mmol) in NMP (2mL) was heated at 180C under microwave for 60min. After cooling down to room temperature, the mixture was treated with a saturated 134 NaHCO3 solution and extracted with EtOAc. The combined organic phases was washed with water (2 times), dried over Na2SO4, and evaporated in vacuo. The crude residue was purified by silica gel flash column chromatography to afford the 135 title compound 18 (168mg, 54%). 1H NMR (300MHz, CDCl3) delta=7.53 (d, J=7.8Hz, 1H), 7.18-7.05 (m, 3H), 7.05-6.91 (m, 4H), 5.20 (s, 2H), 3.77-3.60 (m, 3H), 3.54 (ddd, J=9.7, 7.9, 6.2Hz, 1H), 3.26 (dd, J=9.4, 4.1Hz, 1H), 2.25 (br s, 2H), 2.18-2.06 (m, 1H), 1.79-1.65 (m, 1H)ppm. 13C NMR (75MHz, CDCl3) delta=162.11 (d, J=246.1Hz), 156.76, 142.16, 135.93, 132.52 (d, J=3.1Hz), 127.43 (d, J=8.0Hz), 121.98, 120.25, 116.76, 115.87 (d, J=21.6Hz), 108.28, 58.73, 51.21, 48.95, 47.08, 34.70ppm. HRMS m/z [M+H]+ calcd for C18H20FN4: 311.1666, found: 311.1662.

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; Tian, Junjun; Vandermosten, Leen; Peigneur, Steve; Moreels, Lien; Rozenski, Jef; Tytgat, Jan; Herdewijn, Piet; Van den Steen, Philippe E.; De Jonghe, Steven; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6332 – 6344;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem