Category: imidazoles-derivatives

Electric Literature of 51605-32-4, 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 51605-32-4 as follows.

(1) Ethyl 5-methyl-1H-imidazole-4-carboxylate (Sigma-Aldrich Co., Ltd.) (7.5g, 48.7mmol) in acetonitrile (120mLWas dissolved in), there N-bromosuccinimide (10.4g, 58.4mmol) added The mixture was stirred at room temperature for 3 hours on. After the reaction, a saturated sodium hydrogen carbonate aqueous solution was added, with ethyl acetateIt was extracted twice. The organic layer was washed with saturated brine, and dried with anhydrous sodium sulfate. concentratedAfter it was purified by column chromatography, ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEIJIN PHARMA LIMITED; MARUYAMA, AKINOBU; KAMADA, HIROFUMI; FUJINUMA, MIKA; TAKEUCHI, SUSUMU; SAITO, HIROSHI; TAKAHASHI, YOSHIMASA; (95 pag.)JP2015/214527; (2015); A;,
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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, A new synthetic method of this compound is introduced below., COA of Formula: C19H20N4

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.

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; 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

616-47-7, name is 1-Methyl-1H-imidazole, 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. HPLC of Formula: C4H6N2

1-Methyl-1H-imidazole (20 g, 244 mmol) was dissolved in anhydrous THF (200 mL) under a nitrogen atmosphere. The solution was stirred at -78 C and n-BuLi (167 mL, 268 mmol) was added dropwise slowly at -78 C. After 1 h, CBr4 (97 g, 292 mmol) solution in anhydrous THF (200 mL) was added. The solution was stirred for 2 h at -78 C and for 1 h at room temp. The reaction mixture was quenched with saturated aqueous ammonium chloride (300 mL), extracted with ethyl acetate (2 x 200 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude compound was purified by silica gel chromatography eluting with 60% ethyl acetate in pet. ether to afford the title compound. LCMS (method B): rt = 1.89, [M+H]+= 161.

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BARTON, Nicholas Paul; BERTRAND, Sophie Marie; DOWN, Kenneth; GRAY, Matthew; (168 pag.)WO2019/141694; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10351-75-4,Some common heterocyclic compound, 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, molecular formula is C9H6N2O4, 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 Cd(NO3)2·4H2O (0.0308 g, 0.1 mmol), H3BIDC (0.0412 g, 0.2 mmol) and phen (0.0396 g, 0.2 mmol) with a molar ratio of 1:2:2 were dissolved in the distilled water (5 mL), and stired for 25 min, then set in a Teflon-lined autoclave and heating at 160 C for five days. After cooling to the room temperature, yellow block crystals were obtained. Yield: 28.84 mg (77%, on Cd(II) cations). The products were washed by distilled water and dried in air. Elemental analysis (%): Calc. for 1: C, 52.87; H, 3.74; N, 11.21. Found: C, 52.60; H, 3.38; N, 11.01. IR (KBr pellet, (cm-1)): 3428 (s), 3056 (m), 1717 (w), 1576 (s), 1505 (w), 1472 (w),1384 (m), 1353 (s), 1102 (m), 845 (s), 772 (m). 1H NMR (400 MHz, DMSO-d6): delta=8.97 (d, 2H, phen-H2,9), 8.81 (d, 2H, phen-H4,7), 8.40 (s, 1H, -N=CH-NH), 8.22 (d, 2H, H3BIDC aromatic H), 7.98 (d, 2H, phen-H5,6), 7.96 (d, 2H, phen-H3,8) (ppm).

The synthetic route of 10351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fan, Rui-Qing; Wang, Li-Yuan; Wang, Ping; Chen, Hong; Sun, Cun-Fa; Yang, Yu-Lin; Su, Qing; Journal of Solid State Chemistry; vol. 196; (2012); p. 332 – 340,9;,
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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

Preparation of Olmesartan Medoxomil Example 1 17.3 g (124.8 mmol) of K2CO3, 15 g (62.4 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (III) and 38.3 g (68.7 mmol) 4-[2-(trityltetrazol-5-yl)phenyl]-benzyl bromide (IVa) were suspended in 750 ml of acetonitrile. The suspension was then heated under reflux until the reaction was completed (7 h). 510 ml of acetonitrile were distilled off and the concentrate was cooled to 23 to 25 C. The mixture was stirred at this temperature overnight, then the suspension was cooled to 0 C. and stirred at this temperature for 1 h. The crude product (Va) was filtered off and washed 2* with 20 ml of cooled acetonitrile. Wet product was suspended in 450 ml of water, stirred for 1.5 h and after that filtered off. The mass of dried product (Va) was 39.5 g (89%). T=165-169 C. IR: 1666, 1525, 1291, 1446, 1177, 881, 756, 699, 640

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KRKA; US2009/131680; (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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 33543-78-1

A solution of the required amine (0.20 mmol; 2 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is quenched by the addition of a sat. aq. KH2PO4 solution and the reaction mixture is stirred at rt for 20 h. The reaction mixture is concentrated under reduced pressureand purification of the residue gives the desired product.Example 294 1-[3-(3-ethyl-ureido)-isoquinolin-8-ylmethyl]-1H-imidazole-2-carboxylic acid Starting from the compound of Preparation R and ethyl imidazole-2-carboxylate and proceeding in analogy to Procedure AQ, the title compound was obtained, after purification by prep-HPLC (basic conditions), as an amorphous solid (22percent yield). MS (ESI, m/z): 340.10 [M+H+].

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 33543-78-1.

Reference:
Patent; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 solution of 2-chloro-3-methoxy-5-nitropyridine (1.5 g, 79.78 mmol) in DMSO (15 mL) under an argon atmosphere were added potassium carbonate (4.4 g, 31.91 mmol) and 1H-imidazole-4-carbonitrile (890 mg, 9.57 mmol) at room temperature. The reaction mixture was stirred at 50 oC for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to obtain 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4- carbonitrile (1.1 g, 56percent) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.86 (s, 1H), 8.67 (s, 1H), 8.47 (s, 1H), 4.11 (s, 3H); LCMS: 245.8 (M+1); (column; X-Select CSH C-18 (50 × 3.0 mm, 3.5 mum); RT 2.96 min. 0.05percent aq TFA: ACN; 0.80 mL/min); TLC: 40percent EtOAc:hexane (Rf: 0.4).

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); 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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H3BrN2

To the solution of compound 113-lc (500 mg, 3.4 mmol, 1 eq) in DMF (2.5 mL) was added NaH (163 mg, 4.1 mmol, 60% purity, 1.2 eq) at 0 C. The mixture was stirred at 0 C for 30 min. Then compound 113-lb (460 mg, 3.7 mmol, 351 uL, 1.1 eq) was added to the mixture. The solution was warmed up to 20 C and stirred for 16 hr. The reaction was monitored by LCMS. LCMS showed that the starting material remained and the desired MS was observed. H20 (20 mL) was added to the solution. The mixture was extracted with EtOAc (20 mL*3). The combined organic layer was dried with Na2SC>4 and concentrated under reduced pressure. The residue was purified by to give compound 113-la (100 mg, 528.95 umol, 15.55% yield). It was confirmed by HNMR and HMBC. lH NMR (400MHz, CDC13) delta 7.41 (d, J= 1.3 Hz, 1H), 6.93 (d, J = 1.5 Hz, 1H), 4.37 – 4.27 (m, 1H), 1.48 (d, J= 6.8 Hz, 6H).

The synthetic route of 2302-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 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, 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 144690-33-5, Quality Control of 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

1L glass reaction flask was added with 600ml of acetone, 114.8g of intermediate 1 was added with stirring, then 12.8g of sodium hydroxide was added, the temperature was raised to 50-60 C, and the reaction was incubated for 5 hours, and the reaction was monitored by HPLC. To 20-30 C, add 2.8g potassium iodide, 36.0g 4-chloromethyl-5-methyl-1,3-dioxol-2-one, and increase the temperature to 50-60 C after the addition After 1 hour of heat preservation reaction, the temperature was lowered to 20-30 C, filtered, and the filter cake was rinsed with 115 ml of acetone, and the filtrate was combined. The filtrate was concentrated under reduced pressure at 40-50 C until no obvious solvent flowed out, and 320 ml of acetonitrile was added to cool down. The mixture was decanted to 20-30 C for 1 hour, filtered, and the filter cake was rinsed with 320 ml of acetonitrile. The filter cake was blast dried at 40-50 C for 12 hours to obtain a white solid 110.0 g (intermediate 2). The rate was 85.8%, HPLC: 99.2%.

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Reference:
Patent; Jiashi (Hunan) Pharmaceutical Technology Co., Ltd.; Dai Yongzhi; Liu Hu; Zhu Laifa; Cai Jian; (8 pag.)CN108341804; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17334-08-6,Some common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, molecular formula is C5H8N2O, 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-CARBOMETHOXYIMIDAZOLE After a solution of 3.2 g (8.7 mmol.) of 1-trityl-2-carbomethoxyimidazole in 40 mL of a 5percent solution of acetic acid in methanol was refluxed for 30 minutes, it was concentrated in vacuo. Recrystallization from ethanol afforded colorless needles, mp 187°-188° C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-1H-imidazol-2-yl)methanol, its application will become more common.

Reference:
Patent; Marion Merrell Dow Inc.; US5039691; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem