Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 65039-05-6, name is 1-Butyl-3-methylimidazolium iodide, 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 65039-05-6, Safety of 1-Butyl-3-methylimidazolium iodide

General procedure: Catholyte (0.10 mol L1 of ionic liquid 1a-h in 5.0 mL of organicsolvent) and anolyte (2.0 mL same solvent/electrolyte) wereseparated through a porous glass fritfilled with methylcellulosein DMF-Et4N-BF4. The electrolysis was carried out, under N2atmosphere at 25 C, at a constant current (J = 15 mA cm2). Afterthe consumption of 31 C, the current was switched off, the anodiccompartment removed and the catholyte analyzed by cyclicvoltammetry at different time intervals from the end of theelectrolysis.

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:
Article; Feroci, Marta; Chiarotto, Isabella; D’Anna, Francesca; Forte, Gianpiero; Noto, Renato; Inesi, Achille; Electrochimica Acta; vol. 153; (2015); p. 122 – 129;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 50790-93-7, name is 2-Butylimidazole, 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 50790-93-7, Formula: C7H12N2

Preparation of 6-(2-butylimidazol- 1 -vD-2-chloropurine. A solution of 9-(2,3,5-tri-0-acetyl-beta-D-ribofuranosyi)-2,6-dichloropurine(2.41 g, 5.4 mmol) and 2-butylimidazole (6.68 g, 54 mmol) in CH3CN (60 mL) was stirred at 65 C under N2 for 32 h (reaction complete, TLC). Volatiles were evaporated in vacuo, and the residue was chromatographed (MeOHZCH2Cl2, 1:90) to give crude 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-(2-butylimidazol-l-yl)-2- chloropurine (3.33 g, contaminated with 2-butylimidazole): 1H NMR (500 MHz,CDCl3) delta 8.56 (s, IH), 8.24 (s, IH), 7.10 (s, IH), 6.26 (d, J= 5.8 Hz, IH), 5.83 (t, J = 5.6 Hz, IH), 5.61 (t, J= 5.6 Hz, IH), 4.43-4.51 (m, 3H), 3.31 (t, J= 7.9 Hz, 2H), 2.18 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H), 1.81 (quint, J= 7.7 Hz, 2H), 1.50 (sext, J= 7.7 Hz, 2H), 0.98 (t, J= 7.3 Hz, 3H); HRMS m/z 535.1702 (MH+ [C23H28ClN6O7] = 535.1708).

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, 2-Butylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRIGHAM YOUNG UNIVERSITY, TRANSFER TECHNOLOGY OFFICE; WO2006/138396; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 5851-49-0, 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 5851-49-0 as follows.

General procedure: The respective 1H-benz[d]imidazole(2.50 mmol) was dissolved in 10 ml of abs. DMF. Sodium hydride(60 % dispersion in mineral oil) (0.2 g, 5 mmol) was added withcooling. After the gas formation stopped, 4?-bromomethyl-[1,1?-biphenyl]-2-carbonitrildissolved in 2 ml of abs. DMF was added dropwise and the solution wasstirred for 1 h under cooling in an ice bath and further 2h at RT. Water wasadded and after the solution was acidified with HCl the product was extractedthree times with methylene chloride. The combined organic layers were driedover Na2SO4 and evaporated to dryness in vacuo. The crudeproduct was purified by column chromatography on silica gel with methylenechloride/methanol (95:5) and if necessary recrystallized from diethyl ether/methanol.

According to the analysis of related databases, 5851-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Obermoser, Victoria; Urban, Margarethe E.; Murgueitio, Manuela S.; Wolber, Gerhard; Kintscher, Ulrich; Gust, Ronald; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 138 – 152;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 184098-19-9, 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. 184098-19-9, name is 3-(2-Methyl-1H-imidazol-1-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

A cooled (0 0C) solution of 6-(cyclopropylmethyl(propyl)amino)pyrimidine-4- carboxylic acid (Intermediate 21 , 112 mg; 0.45 mmol) in DCM was treated with diisopropylethylamine (78.4 mL; 0.52 mmol) and methyl chloroformate (36.2 mL; 0.47 mmol). After stirring at 0 0C for 15 minutes, 3-(2-methyl-1 H- imidazol-1-yl)aniline (Maybridge, 117 mg; 0.67 mmol) was added and the mixture stirred for 72 hours. The solvent was evaporated and the compound purified by preparative HPLC to give the title compound as a white solid. 1H NMR (400MHz, CDCI3) delta 10.11 (1 H, s), 8.57 (1 H, s), 7.98 (1 H, t, J = 2.1 Hz), 7.64 (1 H, dd, J = 8.2, 2.0 Hz), 7.47 (1 H, t, J = 8.0 Hz), 7.35 (1 H, s), 7.09- 7.02 (3H, m), 3.53 (4H, s), 2.43 (3H, s), 1.76-1.64 (2H, m), 1.09 (1 H, m), 0.97 (3H, t, J = 7.3 Hz), 0.57 (2H, d, J = 7.7 Hz), 0.35-0.29 (2H, m). MS (ESI+) 391. HPLC (Condition C) Rt 2.33 min (HPLC purity 99.8%).

The chemical industry reduces the impact on the environment during synthesis 3-(2-Methyl-1H-imidazol-1-yl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LABORATOIRES SERONO SA; WO2009/19167; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10394-39-5, name is 5-Methoxy-1-methyl-1H-benzo[d]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 10394-39-5, Formula: C9H10N2O

To a solution of 198 5-methoxy-1-methyl-1H-benzo[d]imidazole (500 mg, 3.08 mmol) in 200 CH2Cl2 (6 ml) was added 201 BBr3 (3.1 g, 12.33 mmol) dropwise at 0 C. After addition, the mixture was stirred for 2 h at 0 C. The mixture was then quenched by slow addition to 202 ice water (50 mL). The resulting mixture was extracted with CH2Cl2 (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the 203 title compound (100 mg, 21.9%) as a white solid which was used in next step without further purification. LCMS (m/z): 149.1 (M+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, 5-Methoxy-1-methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Epizyme, Inc.; Duncan, Kenneth W.; Chesworth, Richard; Boriack-Sjodin, Paula Ann; Munchhof, Michael John; Jin, Lei; (118 pag.)US2019/83482; (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. 914306-50-6, name is 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole

Preparation of compound (15):0.39 g (1 .1 1 mmol) of iridium(lll) chloride trihydrate are dissolved in 1 1.5 ml of an argon-sparged solution consisting of three parts of 2-ethoxyethanol and one part of demineralized water, and also 0.71 g (2.33 mmol, 2.1 eq) of 1 -(2′,6′-di- isopropylphenyl)-2-phenyl-7/-/-imidazole (synthesized analogously to Example 14 in WO 2006/12181 1 ) at room temperature while stirring. The dark green solution is refluxed. Shortly after attainment of reflux, a yellow substance precipitates out. After reaction overnight, the pale yellow suspension cools down and is filtered off with suction. The residue which had been washed with methanol and finally with n-pentane was vacuum-dried at 50C to obtain 0.76 g (82% yield) of the product (15).1H NMR (CD2CI2, 400 MHz): delta = 0.93 (d, 3H), 1.17 (d, 3H), 1.25 (d, 3H), 1 .32 (d, 3H), 2.81 (m, 2H), 6.07 (d, 1 H), 6.23 (d, 1 H), 6.37 (dd, 1 H), 6.51 (dd, 1 H), 6.95 (s, 1 H), 7.39 (m, 2H), 7.56 (d, 1 H), 7.65 (s, 1 H).

The synthetic route of 914306-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; BASF (CHINA) COMPANY LIMITED; MOLT, Oliver; LENNARTZ, Christian; DORMANN, Korinna; FUCHS, Evelyn; GEssNER, Thomas; LANGER, Nicolle; WATANABE, Soichi; SCHILDKNECHT, Christian; WAGENBLAST, Gerhard; WO2012/20327; (2012); 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. 176244-21-6, name is 5,6-Difluoro-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., name: 5,6-Difluoro-1H-benzo[d]imidazol-2(3H)-one

Example 2; Synthesis of 1 -(4-amino-6-methyl- 1 ,3 ,5 -triazin-2-yl)-5 ,6-difluoro-N-( 1 H-pyrazol-5 -yl)- 1 H- benzo[d]imidazol-2-amine; Step l; A sealable vial was charged with l,2-diamino-4,5-difluorobenzene (66.4 mg, 461 mumol), THF (1 rnL), then l,l’-carbonyldimidazole (CDI) (112 mg, 691 mumol). The resulting reaction mixture was maintained at rt for 18 h. The solution was absorbed onto a 5 g silica loading cartridge and passed through a Redi-Sep pre-packed silica gel column (12 g) using a gradient of 1% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2 to afford 5,6-difluoro-lH- benzo[d]imidazol-2(3H)-one as a colorless solid, which was contaminated with CDI biproducts. The solid was transferred to a vial and phosphorus oxychloride (1.265 mL, 13.82 mmol) was added. The reaction mixture was stirred and heated at 90 0C for 18 h and then concentrated for purification by MPLC (Teledine Isco combiFlash Companion). The crude residue was taken up in minimal CH2Cl2 and absorbed onto a 5 g silica loading cartridge and passed through a Redi-Sep pre-packed silica gel column (12 g) using a gradient of 2% EtOAc in hexanes to 90% EtOAc in hexanes to afford 2-chloro-5,6-difluoro-lH- benzo[d]imidazole (49.0 mg, 56.4% yield) as a colorless solid.

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; AMGEN INC.; BOEZIO, Alessandro; CHENG, Alan, C.; COATS, James, R.; COPELAND, Katrina, W.; GRACEFFA, Russell; HARMANGE, Jean-Christophe; HUANG, Hongbing; LA, Daniel; OLIVIERI, Philip, R.; PETERSON, Emily, A.; SCHENKEL, Laurie; WO2010/96314; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 108035-45-6, These common heterocyclic compound, 108035-45-6, name is 4-(1H-Imidazol-2-yl)benzoic acid, 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 281; 4- (1H-Imidazol-2-yl) -N- ( ( 1R, 2S) -2-{ [ (3aR, 4R, 9bR) -4- (methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2- c]quinolin-1-yl]carbonyl}cyclohexyl)benzamide; To a solution of (1R,25)-2-{[(3aR,4R,9bR)-4- (methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2- c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (200 mg, 0.480 mmol) in tetrahydrofuran (5 ml) were added triethylamine (0.199 ml, 1.44 mmol), 4-(1H- imidazol-2-yl) benzoic acid (99.0 mg, 0.529 mmol) and DEPC (0.079 ml, 0.529 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous Mg2S04 and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel and eluted with ethyl acetate-methanol (1: 0-4:1) to give the title compound (150 mg, 61%) as an amorphous form. ¹H-NMR (CDCl3) No.: 1.25-2.50 (11H, m) , 2.96-2.99 (lH, m), 3.34-3.42 (5H, m), 3.54-3.57 (2H, m), 3.70-3. 72 (1H, m), 4.17 (lH, m), 4.30 (lH, m), 5.64 (lH, d, J=6.6 Hz), 6.52 (1H, d, J=7.5 Hz), 6.68 (1H, dd, J=7.5,7.5 Hz), 7.02 (lH, dd, J=7.5,7.5 Hz), 7.15-7.20 (2H, m), 7.36 (lH, d, J=7.5 Hz), 7.42 (lH, d, J=7.5 Hz), 7.83-7.93 (4H, m). LC/MS (ESI) m/z: 514 (MH(at)).

Statistics shows that 4-(1H-Imidazol-2-yl)benzoic acid is playing an increasingly important role. we look forward to future research findings about 108035-45-6.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/105802; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4887-82-5, 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 4887-82-5 as follows.

Intermediate 2; M&lbgammal 5-{5~chloro-1 Mbe?2Jm.d8ZthetaJ-1-v.)-3-{[(1/?)-1-(2-chioro~ 3″hvdroxyphe?yi)ethy?oxy}-2-thiophe?ecaphiochiyiateStep A – Methyi 5-(5-chioro-1 AAbenzimida2ol-1-y.)-3-{[(1 ,1-dimethylethyl)- (climethy.)si.y.]oxy}-2-thiophenecarboxyiateTo a mixture of chiorobe?zimidazole (7,0 g, 48 mmol) and methyl 2-chloro-3- oxo-2,3-dihydro-2-thk>phenecarboxyiate (Synthesis,, 1984,, IQ1 847-850) (9.8 g, 51 mmol) in 400 mL of chloroform was added /V-methyiimidazoie (5.5 mL, 89 mmoi). After 16 h, fe/f-buiyfchlorodimethyisilane (8.9 g, 46 mmol) and lambdaA methylimidazoie (3.7 ml, 48 mmol) was added. The reaction mixture was diluted with water and the layers were separated. The aqueous phase was extracted with DCW. The combined organic layers were washed with water, dried over MgSO4 and concentrated onto silica gel The crude material was purified by flash column chromatography (0-100% 25% EtOAc/hexanes) to give 5,8 g of the desired product (30%). 1H NMR (400 MHz, Cl6-DMSO) delta 8.79 (ss 1H), 7.8S (ci, ,/ =2.0 Hz1 IH), 7.81 (d, J =%alpha HZ1 1H)1 7,44 (dd, J^8,8 and 2.0 Hz, 1H), 7,25 (s. 1H), 3.78 (s, 3H), 0.99 (s, 9H), 0.27 (s, QH).

According to the analysis of related databases, 4887-82-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
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. 67014-36-2, name is 5-Amino-6-methyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H9N3O

1.59 g (6.13 mmol) of ethyl 3-ethoxy-2-[(ethoxycarbonyl)carbamoyl]acrylate (for preparation see: Senda, Shigeo; Hirota, Kosaku; Notani, Jiyoji, Chemical & Pharmaceutical Bulletin (1972), 20(7), 1380-8) and 1.00 g (6.13 mmol) of 5-amino-6-methyl-1,3-dihydro-2H-benzimidazol-2-one were heated to reflux in 46 ml of ethanol for 2 h. Thereafter, 0.69 g (6.13 mmol) of potassium tert-butoxide were added at RT and the reaction mixture was stirred at RT overnight and at reflux for 1 h. For workup, the reaction mixture was admixed with water and acidified with 1N hydrochloric acid. The solid formed was filtered off, washed with water and ethyl acetate, and then dried under reduced pressure at 50 C. This gave 1.46 g (72% of theory) of the target compound. LC-MS (Method 1): Rt=0.52 min; MS (ESIpos): m/z=331 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.22 (t, 3H), 2.08 (s, 3H), 4.16 (q, 2H), 6.89 (s, 1H), 7.03 (s, 1H), 8.19 (s, 1H), 10.77 (s, 1H), 10.78 (s, 1H), 11.65 (s, 1H).

According to the analysis of related databases, 67014-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem