Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, 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 714273-83-3, Recommanded Product: 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde

Example 1 Preparation of 5-(tert-butyl)-1H-imidazole-4-carbaldehyde-d (deuterium aldehyde compound b), as Show in the Following Figure The specific process for preparing the compound comprises the following step: 5-(tert-butyl)-1H-imidazole-4-carbaldehyde (304 mg, 2 mmol) was weighed and added into a dry and round bottom flask with a volume of 50 mL, and nitrogen was aerated for protection. anhydrous EtOH (5 mL) and NaBD4 (420 mg, 10 mmol) was added into the reaction flask under nitrogen. The resultant mixture was reacted overnight at room temperature. To the quenching reaction, 10 mL water was added. The organic phase was extracted by ethyl acetate. The product was spin-dryed and to be used for the next step directly. 10 mL acetone and MnO2 (1.7 g, 20 mmol) was added, and reaction was carried out overnight at room temperature. Carrying out suction filtration via the sand core funnel, spin-drying the solvent, carrying out column chromatography isolation and purification to obtain off-white solid of 5-tert-butyl-1H-imidazole-4-carbaldehyde-d (199 mg, 1.3 mmol), with yield of 65%. 1H NMR (400 MHz, DMSO-d6) delta 6.97 (s, 1H), 6.66 (s, 1H) 1.05 (s, 9H); MS (ESI) m/z 154.10 (M+H)+ (calcd for C8H12DN2O 154.10).

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; MARINE BIOMEDICAL RESEARCH INSTITUTE OF QINGDAO CO., LTD.; LI, Wenbao; SUN, Tianwen; WANG, Shixiao; ZHAO, Jianchun; CAI, Bing; GUAN, Huashi; (17 pag.)US2018/140600; (2018); A1;,
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Imidazole | C3H4N2 – PubChem

Related Products of 614-97-1, 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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Equimolar quantities of the 7-bromo alkane derivatives (2a-2c) and corresponding benzimidazole were dissolved in acetone (30 mL), and certain amount of K2CO3 was also added to the solution. The solution was then refluxed for approximately 12 h. The product was extracted by dichloromethane. Then evaporated of the solvent, the residue was purified bycolumn chromatography on silica gel, eluting with dichloromethane/methanol (30:1) to givethe compounds 3-23.

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

Reference:
Article in Press; Wang, Zhe; Deng, Xiangping; Xiong, Shujuan; Xiong, Runde; Liu, Juan; Zou, Liu; Lei, Xiaoyong; Cao, Xuan; Xie, Zhizhong; Chen, Yanming; Liu, Yunmei; Zheng, Xing; Tang, Guotao; Natural Product Research; (2017); p. 1 – 10;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 1977-72-6, These common heterocyclic compound, 1977-72-6, name is 5-Fluoro-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.

CuBr 6 mg (0.04 mmol), TEMPO 5 mg (0.03 mmol), compounded in a 25 mL Schlenk reaction tube5-fluorobenzimidazole 55 mg (0.4 mmol),28 mg (0.2 mmol) of salicylic acid (0.2 mmol) and p-xylene (0.5 mL), followed by 33 muL of pyridine (0.4 mmol) were added and the reaction was stirred at 120°C for 36 hours under reflux.Cool to room temperature, transfer all to a 25 mL flask, spin off the solvent on a rotary evaporator, add an appropriate amount of silica gel to spin dry, and then use a 300-400 mesh silica gel column. The developing solvent used is petroleum ether:ethyl acetate=16: 1 to 6:1, that is, compound III-6 15 mg, yield 30percent, white solid

Statistics shows that 5-Fluoro-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 1977-72-6.

Reference:
Patent; Southwest University; Cai Guixin; Xie Dan; (14 pag.)CN107955020; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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 39021-62-0, Product Details of 39021-62-0

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (3.0 g, 6.97 mmol, Intermediate 5: step d) was added THF (40 mL) and the solution was cooled to -70 C. n-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was then added dropwise. After 2 minutes, 1-methyl-1H-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C. bath. After 35 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc:THF (10:2, 5*50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. Chromatography on silica gel (30% acetone-DCM increasing to 5% MeOH) provided the title compound.

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, 1-Methyl-1H-imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

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; Cummings, Maxwell D.; (53 pag.)US2017/258782; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 37052-78-1,Some common heterocyclic compound, 37052-78-1, name is 5-Methoxy-1H-benzo[d]imidazole-2-thiol, molecular formula is C8H8N2OS, 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.

[Reference Example 7] Production of 4-(5-methoxybenzimidazole-2-ylthio)butanoate ester hydrogen bromide salt 6.48 g (33.2 mmol) of 4-bromobutanoate ethyl ester were added to 10 ml of an ethanol solution containing 5.0 g (27.7 mmol) of 5-methoxybenzimidazole-2-thiol followed by stirring for 1 hour at 80C and adding 90 ml of ethyl acetate. The reaction solution was returned to room temperature and the formed crystals were filtered out followed by drying to obtain 9.34 g of the target compound (yield: 90%). 1H-NMR (270 MHz, CDCl3) (ppm): 7.65 (d,1H,J=8.91 Hz), 7.24 (S,1H), 7.00 (dd,1H,J=2.43, 8.91 Hz), 4.21 (q,2H,J=7.29 Hz), 3.83 (s,3H), 3.74 (m,2H), 2.61 (m,2H), 2.10 (m,2H), 1.30 (t,3H,J=7.29 Hz)

The synthetic route of 37052-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEIJIN LIMITED; EP1249450; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 46006-36-4, name is 1H-Benzimidazole-7-carboxylic 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 46006-36-4, Formula: C8H6N2O2

B. (lH-Benzo[d]imidazol-4-yI)methanol.; lH-Benzo[d]imidazole-4- carboxylic acid (1.04 g, 6.41 mmol) was suspended in anhydrous tetrahydrofuran (80 mL) and cooled to -78 0C. A solution of lithium aluminum hydride in tetrahydrofuran (2.0M, 6.4 mL) was added via syringe. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with methanol and adsorbed onto silica gel. Flash chromatography (20% MeOH in EtOAc) afforded a white solid (550 mg, 3.72 mmol, 58%). MS (ESI) m/z 149.0 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzimidazole-7-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, 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. Product Details of 10597-52-1

To a stirred suspension of sodium hydride (665 mg, 16.64 mmol) in DMF (90 mL) at rt was added 4-nitro-1H-benzimidazole (2714 mg, 16.64 mmol) in several portions. After stirring for 1 h, 4-fluorobenzonitrile (1350 mg, 11.146 mmol) was added and the mixture was stirred for 15 h at 130C. After cooling, water was added, the precipitate was filtered off, washed with water and dried to yield 4-(4-nitro-benzoimidazol-1 -yl)-benzonitrile (2.47 g, 47.76 %).1H-NMR (300 MHz, d6-DMSO): delta =8.92 (1H), 8.16 8.11 (3H), 8.08 (1H), 7.97 (1H), 7.95 (1H), 7.53 (1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10597-52-1, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; KOPPITZ, Marcus; NGUYEN, Duy; KOSEMUND, Dirk; NEUHAUS, Roland; SIEMEISTER, Gerhard; WO2012/130905; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, molecular formula is C5H7BrN2, 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. Application In Synthesis of 5-Bromo-1,2-dimethyl-1H-imidazole

Example 67: (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)bis(1,2-dimethyl-1H-imidazol-5-yl)methanol A solution of n-BuLi (2.5 M in hexanes, 0.24 mL, 0.6 mmol) was added dropwise by syringe to a solution of 5-bromo-l ,2-dimethyl-lH-imidazole (107.8 mg, 0.616 mmol) in dry THF (6 mL) in a dry ice-acetone bath. After 1-2 minutes, (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin~6- yl)( 1 ,2-dimethyl- lH-imidazol-5-yl)methanone (0.217 g, 0.512 mmol, Intermediate 46: step b) in dry THF (2 mL) was added to the mixture via syringe. After 5 minutes, the reaction was removed from the cold bath and was allowed to warm to ambient temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride. Water was added and the aqueous mixture was extracted with dichloromethane. The combined organic layers were dried (Na^SC ), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel 0-10% MeOH-DCM) to provide the title compound, NMR (400 MHz, CDC13) delta 8.23 (d, J = 2.2 Hz, 1H), 7.63 (d, J = 8.7 Hz, 1H), 7.37 (dd, J = 8.8, 2.1 Hz, i l l). 7.30 – 7.25 (m, 2H), 6.97 – 6.92 (m, 21 1). 6.19 (s, 1H), 6.12 (s, 21 1). 4.22 (s, 2H), 4.07 (s, 3H), 3.37 (s, 6H), 2.24 (s, 6H); MS m/e 520.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24134-09-6, its application will become more common.

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; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 2302-25-2, name is 4-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromo-1H-imidazole

[00328] To a flask was added 4-bromo-5H-imidazole (approximately 455 mg, 3.1 mmol) in N-methylpyrrolidine (6 mL) and 3,5-difluoropyridine (366 mg, 3.1 mmol) and potassium carbonate (429 mg, 3.1 mmol). The reaction was heated at 100 C for 12 hours. LCMS showed the formation of the product. The reaction was filtered and the crude product was purified by reverse phase chromatography (CI 8 100 g column (ISCO);10-90% water/acetonitrile with a trifluoroacetic acid modifier) to afford purified product. The fraction were combined and neutralized with an SPE-CO3H cartridge to afford the desired product.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; COLLIER, Philip, N.; DAVIES, Robert, J.; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GOLDMAN, Brian, Anthony; GRILLOT, Anne-Laure; KOLPAK, Adrienne, Lynne; KRAUSS, Raul, Eduardo; LEDFORD, Brian; LIAO, Yusheng; MAGAVI, Sanjay, Shivayogi; MALTAIS, Francois; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; TANG, Qing; WANG, Tiansheng; (221 pag.)WO2018/106643; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-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. Recommanded Product: 15965-54-5

Reference Example 52 5-Methoxy-2-chlorobenzimidazole (0.55 g), thiourea (0.2 g) and ethanol (10 ml) were refluxed for 2 hours. To the reaction mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.51 g) and sodium hydroxide (0.3 g) in water (5 ml) and the mixture was refluxed for 5 hours. After completion of the reaction, ethanol was distilled off and water was added to the resulting residue, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.62 g). NMR (CDCl3)delta: 1.60-2.00 (2H, m), 2.70 (2H, t, J=7Hz), 2.73 (3H, s), 2.83-3.23 (2H, m), 3.73 (3H, s), 4.30 (2H, s), 6.67-7.40 (6H, m), 12.50 (1H, br.) In a manner analogous to Reference Example 52, the same compounds as those obtained in Examples numbered between 35 and 156 were produced using appropriate starting materials.

The synthetic route of 2-Chloro-5-methoxy-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP239129; (1991); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem