Tag: M.W=100-200

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

Electric Literature of 39070-14-9, 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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The corresponding hydroxy startingcompound (1a, 2a and 3a) (2 mmol) in tetrahydrofuran (10 mL) was added to phosgene (4 mL,8 mmol) and tetrahydrofuran (THF) (15 mL) at 0 C. The reaction mixture was stirred for 16 h, then the solvent was removed in vacuo. The crude chloroformate was used without further purification.

The chemical industry reduces the impact on the environment during synthesis (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol. I believe this compound will play a more active role in future production and life.

Reference:
Article; Anduran, Emilie; Aspatwar, Ashok; Bua, Silvia; Dubois, Ludwig; Lambin, Philippe; Nocentini, Alessio; Parkkila, Seppo; Parvathaneni, Nanda-Kumar; Supuran, Claudiu T.; Suylen, Dennis; Winum, Jean-Yves; Molecules; vol. 25; 10; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2302-25-2,Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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 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).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-imidazole, its application will become more common.

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

Synthetic Route of 32673-41-9, A common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step A 4-(Hydroxymethyl)-1-(triphenylmethyl)imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white 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; Merck & Co., Inc.; US6410534; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 360-97-4, 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. 360-97-4 name is 4-Amino-1H-imidazole-5-carboxamide, 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.

A solution of 5-amino-1H-imidazole-4-carboxamide (820mg, 6.5mmol), compound 40a (1.83 mg,6.5 mmol), and Et3N (3 mL) in dry acetonitrile (40 mL) was heated at 50 C for 16 h. After cooling,The brown solid precipitated was collected by filtration and washed with H2O to affordcompound 40b (433 mg, 37%) without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-1H-imidazole-5-carboxamide, and friends who are interested can also refer to it.

Reference:
Article; Bai, Gang; Cai, Shi; Chen, Yun; Ding, Jian; Duan, Wenhu; Ning, Yi; Song, Peiran; Xie, Hua; Zhang, Huibin; Zhang, Tao; Zhou, Jinpei; European Journal of Medicinal Chemistry; vol. 190; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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 705-09-9

4-(4,6-Dichloro-1,3,5-triazin-2-yl)morpholine was added to a 500 mL single-mouth bottle (2)11.33g (48.2mmol), anhydrous potassium carbonate 6.66g (48.2mmol), DMF 150mL2-Difluoromethyl-1H-benzimidazole (3) 8.10 g (48.2 mmol) was added with stirring.2 hours at room temperature, add 200 mL of water, let stand, precipitate solids, filter under reduced pressure, with a small amountIt was washed with water and dried to give a white powdery solid 15.21 g The crude product yield was 86.03%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 705-09-9, its application will become more common.

Reference:
Patent; Shenyang Pharmaceutical University; Sun Tiemin; Zhou Zhixu; Du Lei; Yan Ning; Wang Yude; Li Linwei; (14 pag.)CN105130960; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 35203-44-2, 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. 35203-44-2 name is 1-Propyl-1H-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.

(Reference Example 19) Synthesis of 1-propyl-1H-imidazole-2-carbaldehyde: A solution of 1-propyl-1H-imidazole (1.67 g, 15.2 mmol) in tetrahydrofuran (30.4 mL) was cooled to -78°C. n-Butyllithium (1.62 M n-hexane solution, 10.3 mL, 16.7 mmol) was added to the reaction liquid at -78°C. The reaction liquid was stirred at the same temperature for 1 hour and then N,N-dimethylformamide (1.41 mL, 18.2 mmol) was added at -78°C. After the reaction liquid was stirred at the same temperature for 1 hour, the temperature of the reaction liquid was raised to room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction liquid and then ethyl acetate was added. The organic layer was washed with a 10percent aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate) to obtain 1-propyl-1H-imidazole-2-carbaldehyde (0.492 g, 3.56 mmol, 24percent) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 0.91-0.95 (3H, m), 1.79-1.84 (2H, m), 4.34-4.38 (2H, m), 7.15 (1H, s), 7.28 (1H, s), 9.82 (1H, s). ESI-MS: m/z= 139 (M+H)+.

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

Reference:
Patent; Toray Industries, Inc.; ARAI Tadamasa; MORITA Yasuhiro; UDAGAWA Shuji; ISEKI Katsuhiko; IZUMIMOTO Naoki; (95 pag.)EP3263565; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-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 89830-98-8, HPLC of Formula: C6H8N2

To a solution of 3-bromo-7,8-dihydro-6H-1,6-naphthyridin-5-one (0.100 g, 0.437mmol) and 4-cyclopropyl-1H-imidazole (0.0709 g, 0.65 5 mmol) in DMF (5.00 mL) is addedK2C03 (0.18 1 g, 1.31 mmol). The mixture is degassed with a stream of N2 for 5 minutes. DMEDA (0.0193 g, 0.218 mmol) and CuT (0.0832 g, 0.437 mmol) are added sequentially and the resulting mixture is stirred at 110 C for 16 hours under N2. The mixture is extracted with EtOAc (2x75mL) and washed with saturated brine (3 x25 mL). The organic extracts aredried over Na2SO4, filtered, and evaporated to dryness. The crude product is purified by silica gel flash chromatography, eluting with a gradient of 0% to 5% MeOH in DCM to give the title compound (0.060 g, 48.6%) as a light green solid. ES/MS (m/z): 255.0 (M+H), ?H NMR (400 IVIHz, CDC13) 8.74 (d, J=3.2 Hz, 1H), 8.33 (d, J=2.4 Hz, 1H), 7.81 (s, 1H), 7.10 (s, 1H), 6.31 (br s, 1H), 3.73 (dt, J=3.2, 6.8 Hz, 2H), 3.39 -3.15 (m, 2H), 1.99- 1.90 (m, 1H),0.96-0.88(m,4H)

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

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD; LEI, Hui; LIU, Gang; TIAN, Yuan; ZHANG, Haizhen; (0 pag.)WO2018/160406; (2018); 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5BrN2

A solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.689 mmol) was added dropwise, over a 25 minutes period, to a solution of 5-bromo-1-methyl-1H-imidazole (4.1 g, 25.689 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.408 mmol, Intermediate 40: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and layers separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and precipitates filtered to provide the title compound as a tan 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; 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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); 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. 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H10N2

The synthesis of 1-methyl-2-phenyl-1H-benzoimidazole (Mpb) is accomplished by referring to methods disclosed in Popov, 1. I., Chem. Heterocycl. Compd. (EN), 1996, 32, 6, p.672-681. The synthetic method is outlined in Scheme 1. To 20 mL acetone was added 2-phenyl-1H-benzoimidazole (1.94 g, 10 mmol), followed by the injection of iodomethane (1.42 mL, 12 mmol). The mixture was stirred at room temperature for 6 h, sodium hydroxide solution was then added, and the mixture reacted for an additional 5 min. The reaction mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using n-hexanes/EA (v/v=80/20) as eluent. After the product was completely isolated, 1.03 mg (0.49 mmol) of the title compound was obtained (49percent yield). 1H NMR (CDCl3, delta): 3.87 (s, 3 H), 7.32-7.41 (m, 3 H), 7.51-7.56 (m, 3 H), 7.83-7.86 (m, 3 H).

According to the analysis of related databases, 716-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheng, Chien-Hong; Chen, Ruey-Min; Guo, Hong-Ru; Chung, Jun-Wen; US2005/116626; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem