Month: July 2021

These common heterocyclic compound, 1848-84-6, name is 2-Ethyl-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. SDS of cas: 1848-84-6

A mixture of [2-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)-ethyl]- (l,l-dioxo-tetrahydro-l-thiophen-3-yl)amine (45 mg, 0.11 mmol), 2-ethylbenzimidazole (18 mg, 0.12 mmol), Pd2(dba)3 (2.5 mg, 2.5 molpercent), Xphos (5.2 mg, 10 molpercent) and Cs2CO3 (53 mg, 0.16 mmol) in dioxane (1.5 mL) was purged with argon gas then heated at 120 °C, for 4 h, in a sealed tube. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3/MeOH in DCM. The resulting residue was purified by column chromatography (Si-PCC, 0-10percent MeOH in DCM) to give 595 (35 mg, 62percent) as a pale yellow solid. LCMS: (Method I): Rx 2.43 min, [M+H]+ 525.2 1H NMR (300 MHz, CDCl3d): delta 8.02-7.98 (m, 1 H), 7.78-7.74 (m, 1 H), 7.31-7.23 (m, 2 H), 4.50-4.95 (m, 4 H), 3.87 (t, J = 4.7 Hz, 4 H), 3.76 (s, 3 H), 3.73-3.67 (m, 1 H), 3.40- 3.24 (m, 4 H), 3.23-3.14 (m, 2 H), 3.14-3.00 (m, 4 H), 2.94 (dd, J = 13.2, 6.0 Hz, 1 H), 2.49- 2.45 (m, 1 H), 2.15-2.05 (m, 1 H), 1.44 (t, J = 7.5 Hz, 3 H)

The synthetic route of 2-Ethyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); 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. 583-39-1, name is 2-Mercaptobenzimidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Mercaptobenzimidazole

a. A mixture of 0.46 g (0.0016 mol) of benzyl acetate 6, 0.25 g (0.0016 mol) of 1,3-dihydrobenzimidazole-2-thione, 3 mL of acetone, and 3 mL of formic acid was heated at 40C for 6 h. The reaction mixture was cooled down to ambient temperature and poured into aqueous NaCl. The precipitate that formed was filtered off, washed with water, and dried in air. Yield 0.56 g (92%), mp 168-170C (benzene). 1H NMR spectrum (CDCl3), delta,ppm: 1.34 s (18H, CMe3), 4.73 s (2H, CH2N), 5.23 s(1H, OH), 7.17 s (2H, ArH), 7.23-7.30 m (2H, H5,6),7.71-7.78 m (2H, H4,7). Found, %: C 71.45; H 7.83; N 7.27. C22H28N2OS. Calculated, %: C 71.70; H 7.66; N 7.60. b. A solution of benzyl acetate 6 and 1,3-dihydrobenzimidazole-2-thione in a 1 : 1 mixture of acetone and formic acid at ambient temperature for 2 days to obtain 98% of compound 12.

The synthetic route of 583-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tagasheva; Gataullina; Zaripova; Bukharov; Nugumanova; Deberdeev; Voronina, Yu. K.; Russian Journal of General Chemistry; vol. 87; 1; (2017); p. 22 – 28; Zh. Obshch. Khim.; vol. 87; 1; (2017); p. 26 – 32,7;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 106429-59-8,Some common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, molecular formula is C8H6N2O2, 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.

Step 3.5-((7-(5-(4-fluoro-2-(3-hydroxypentan-3-yl)phenoxy)pyrimidin-4-yl)-2,7- diazaspiro[4.4]nonan-2-yl)methyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one (0942) To a solution of crude 3-(2-((4-(2,7-diazaspiro[4.4]nonan-2-yl)pyrimidin-5- yl)oxy)-5-fluorophenyl)pentan-3-ol from above and 2-oxo-2,3-dihydro-1H- benzo[d]imidazole-5-carbaldehyde (Intermediate 40, 20 mg, 0.12 mmol) in MeOH (3 mL) was added NaBH3CN (10 mg, 0.16 mmol) at RT and the reaction mixture stirred for 4 h. Evaporation of the solvent followed by RP-HPLC method A afforded 5-((7-(5-(4- fluoro-2-(3-hydroxypentan-3-yl)phenoxy)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2- yl)methyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one. LCMS method G: Rt = 3.197 min; (M+H)+ = 547.61.1H NMR (CD3OD): delta 8.52 (bs, 1H), 7.60 (m, 1H), 7.45 (dd, J = 2.8, 10.6 Hz, 1H), 7.21-7.18 (m, 2H), 7.11 (d, J = 8.4 Hz, 2H), 7.05-6.96 (m, 1H), 4.43 (s, 2H), 4.20-3.90 (m, 4H), 3.70-3.50 (m, 2H), 3.48-3.33 (m, 2H), 2.34-1.90 (m, 6H), 1.89- 1.80 (m, 2H), 0.78 (t, J = 7.2 Hz, 6H).

The synthetic route of 106429-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, 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. COA of Formula: C12H11N3O

3-Methoxy-4-(4-methyl-lH-imidazol-l-yl)benzonitrile (100 mg, 0.469 mmol) was placed in a reaction vessel, and a 5 M aqueous sodium hydroxide solution (1 mL) and methanol (2 mL) were successively added to the vessel. The resultant mixture was stirred at room temperature for 2 hours, and then further stirred at 65C for 5 hours. The resultant reaction mixture was concentrated under a reduced pressure, and a 2 M aqueous hydrochloric acid solution (4 mL) and water (4 mL) were successively added to the concentrate. The solids collected by filtration were dried under a reduced pressure to obtain 98 mg of a title compound. Yield: 78%.

The synthetic route of 1243204-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management CO., LTD.; YOSHIKAWA, Seiji; KAYANO, Akio; WO2011/37244; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33468-69-8, 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 33468-69-8 as follows.

Sodium hydride (7.91 mg, 0.198 mmol, 60% in mineral oil) was added to a solution of 4- (trifluoromethyl)-I H-imidazole (24.46 mg, 0.180 mmol) in dry N,N-dimethylformamide (0.4 ml). The reaction was stirred at room temperature for 30 minutes until gas evolution ceased. A solution of 2-(5- bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfanyl-5-(trifluoromethyl)pyridine (66.0 mg, 0.180 mmol) in N,N-dimethylformamide (2.0 ml) was slowly added and the reaction mixture stirred at room (0511) temperature for 30 minutes. Two more equivalents of the previously described solution consisting of sodium hydride and 4-(trifluoromethyl)-1 H-imidazole were then added and stirring continued overnight at 60C. The mixture was quenched over water and ethyl acetate, the layers separated, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (cyclohexane/ethyl acetate) to afford 3-ethylsulfanyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]-5- (trifluoromethyl)pyridine (compound P2) as a solid (55 mg). LCMS (method 4): 423 (M+H)+, retention time 0.97 min. H-NMR (CDCb, ppm) 8.70 (t, 1 H), 8.00 (d, 1 H), 7.94 (d, 1 H), 7.71 (m, 1 H), 3.81 (s, 3H), 3.06 (q, 2H), 1.42 (t, 3H).

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; MUEHLEBACH, Michel; EDMUNDS, Andrew; RENOLD, Peter; BUCHHOLZ, Anke; (96 pag.)WO2018/41729; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4857-06-1 name is 2-Chloro-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-Chloro-5,6-dibromobenzimidazole (17) To a suspension of 0.763 g (5 mmole) of 2-chlorobenzimidazole in 50 mL of 1:1 MeOH/H2 O, was added dropwise a solution of 1 mL of Br2 in 10 mL of MeOH over a period of 30 min. The reaction mixture was stirred at room temperature overnight and was then filtered. The solid was washed with portions of H2 O until the washings were neutral. This solid was air dried and recrystallized from MeOH to give 1.115 g (3 crops, 72%) of 17. mp 228 C.; 1 H NMR (DMSO-d6) d 13-14 (br. s, 1,1-NH), 7.93 (s, 2,4-H, 7-H).

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

Reference:
Patent; The Regents of the University of Michigan; US5360795; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-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 705-09-9, SDS of cas: 705-09-9

Compound 2 (425 muetaetaomicronIota, 1.0 eq.) is dissolved in DMF (2 ml) and cooled to -5C, treated with anhydrous potassium carbonate (1 .44 eq.) and 2-(difluoromethyl)-1 H-benzo[c/]- imidazole (1 .4 eq.), stirred for 30 min and further stirred at room temperature for 4 h. The reaction mixture is diluted with water and the precipitate is filtered and washed with small amounts of water. Purification is done by silica gel flash column chromatography. Rf: 0.72 (methylene chloride/methanol, 95:5 v/v); 1H NMR (CDCI3, 400 MHz) delta 8.43 (d, J = 7.8 Hz, 1 H), 7.90 (d, J = 7.6 Hz, 1 H), 7.71 -7.43 (m, 3H), 4.00-3.95 (m, 4H), 3.86-3.80 (m, 4H); 19F NMR (CDCI3, 400 MHz) delta -1 19.20 (d, J = 53.9 Hz, 2F).

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-(Difluoromethyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF BASEL; CMILJANOVIC, Vladimir; CMILJANOVIC, Natasa; GIESE, Bernd; WYMANN, Matthias; WO2011/135520; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 621-72-7, 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. 621-72-7, name is 2-Benzyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Metallic Na (76 mg,3.3 mmol) was added to t-BuOH (30 ml), and the mixturewas heated under reflux until effervescence ceased. Thenazole 3b-d or 6b,d,e (3 mmol) and 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole (1) (0.99 g, 3 mmol)were added. The reaction mixture was heated under refluxfor 2 h (for compounds 4b-d, 7d,e) or 3 h (for compound7b). The solvent was evaporated under reduced pressure,and H2O (15 ml) was added to the residue. The precipitatewas filtered off, dried at 60C, and recrystallized from asuitable solvent.

The synthetic route of 2-Benzyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Makarova, Nadezhda N.; Klen, Elena E.; Khaliullin, Ferkat ?.; Chemistry of Heterocyclic Compounds; vol. 55; 9; (2019); p. 823 – 826; Khim. Geterotsikl. Soedin.; vol. 55; 9; (2019); p. 823 – 826,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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. COA of Formula: C3H4N2

General procedure: A mixture of imidazole (22 mmol, 1 equiv) and the alkyl bromide (1equiv) in toluene (30 mL) in the presence of tetraethylammonium iodide(0.2 equiv) and sodium hydroxide (3 equiv) was heated at refluxtemperature for 10 h. The resulting mixture was cooled to room temperature,water was added, and the mixture extracted twice with ethylacetate. The combined organic extracts were washed with brine, driedover sodium sulfate, and concentrated. Purification by flash-columnchromatography on silica gel using ethyl acetate as an eluent, followedby drying under high vacuum gave the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Article; Brockhausen, Inka; Kocev, Alexander; Kong, Xianqi; Melamed, Jacob; Szarek, Walter A.; Vlahakis, Jason Z.; Wang, Shuo; Xu, Yaozu; Bioorganic and medicinal chemistry; (2020);,
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. 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, A new synthetic method of this compound is introduced below., Recommanded Product: 2466-76-4

Add 1-acetylimidazole (0.035 g, 0.315 mmol) and triethylamine (0.04 mL, 0.286 mmol) to solution of 2-(R)-[2-(S)-amino-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]- piperidine-1-carboxylic acid tert-butyl ester (0.106 mg, 0.286 mmol) in dichloromethane (10 mL) and stir 18 h at room temperature. Dilute with ethyl acetate and wash with 1 N hydrochloric acid (3x), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with dichloromethane and ethyl acetate) to give the title compound as a white solid (0.089 g, 76percent). MS (ES): m/z = 411.2 [M-H].

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/108358; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem