Tag: M.W=200-300

Related Products of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

18(a) Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 0.26 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 0.72 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 5 ml of N,N-dimethylformamide was then added, and the reaction mixture was stirred at room temperature for 2 hours and then at 60 C. for 4 hours. At the end of this time, it was dissolved in ethyl acetate and the solution was washed three times with water. The solution was then dried over anhydrous sodium sulfate, after which it was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.62 g of the title compound as an amorphous solid. This was crystallized from diisopropyl ether, to give the title compound as crystals, melting at 167-168 C. (with decomposition). Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.88 (3H, triplet, J=7 Hz); 1.08 (3H, triplet, J=7 Hz); 1.5-1.8 (2H, multiplet); 1.64 (6H, singlet); 2.52 (2H, triplet, J=8 Hz); 4.12 (2H, quartet, J=7 Hz); 5.38 (2H, singlet); 5.78 (1H, singlet); 6.7-7.6 (22H, multiplet); 7.8-8.1 (1H, multiplet).

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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 641571-11-1

A solution of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline(524 mg, 2.0 mmol) and Et3N (10 mmol) in anhydrous THF (6 mL) wascooled to 0 C in an ice bath. The light yellow solution preparedbefore was then added dropwise. The mixture was allowed to warm toroom temperatureand maintained for 1 h. The reaction mixture was quenched by addition of saturatedNaCl solution and the reaction mixture was extracted several times with EtOAc.Thecombined organic extracts were dried with Na2SO4,filtered, and concentrated in vacuo. The resultant crudematerial was purifiedby column chromatography to give the title compound 7 (873 mg, yield 90% of two steps). 1H NMR (400 MHz, DMSO-d6) d 10.80 (s, 1H), 8.66 (s, 1H),8.47 (d, J = 1.6 Hz, 1H), 8.39 (s, 1H), 8.19 (s, 1H), 7.98 (dd, J = 1.6, 8.0Hz, 1H), 7.79 (s, 1H), 7.66 (s, 1H), 7.53 (d, J = 8.0 Hz ,1H), 2.46 (s, 3H),2.24 (s, 3H). LC-MS (ESI):m/z 486 [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 641571-11-1, its application will become more common.

Reference:
Article; Lu, Xiaoyun; Zhang, Zhang; Ren, Xiaomei; Pan, Xiaofeng; Wang, Deping; Zhuang, Xiaoxi; Luo, Jingfeng; Yu, Rongmin; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3458 – 3463;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, 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: 150058-27-8

BIM (20 g, 1 eq) was dissolved in dimethylacetamide:methanol [(1:4), (100 mL, 5 vol)], potassium carbonate (18.8 g, 1.5 eq) was added thereto, and the mixture was stirred at 25¡ãC – 30¡ãC for 15 min. Furthermore, BCL (34.4 g, 1.05 eq) and tetrabutylammonium iodide (1.67 g, 0.05 eq) were added thereto, and the mixture was stirred at the same temperature for 26 hr. Using TLC (TLC: 40percent ethyl acetate/hexane, detection method: UV), complete consumption of BIM was confirmed. To the reaction mixture was added water (200 mL, 10 vol), the mixture was stirred for 2 hr, and the precipitated pink solid was filtered. The obtained solid was washed with water (40 mL, 2 vol), dried with suction for 15 min, and blast dried at 50¡ãC – 55¡ãC for 4 hr to give a mixture of crude CBME and compound 37 (49 g, CBME:compound 37=6:1 (molar ratio)). The crude product was directly used for the next step (4).

The synthetic route of Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; API Corporation; SEKI, Masahiko; EP2891650; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 40644-16-4,Some common heterocyclic compound, 40644-16-4, name is 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5BrN2O, 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: 4-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol- 2-one To a solution of 4-bromo-1 ,3-dihydro-benzoimidazol-2-one (701 mg, 3.29 mmol) in dimethyl sulfoxide (2 ml_) was added potassium acetate (803 g, 10.9 mmol), 1,1′-bis(diphenyl phosphino) ferrocene palladium chloride (PdCI2 (dppf)) (134 mg, 0.16 mmol) and bis(pinacolato) diboron (1.67 g, 6.58 mmol). The mixture was degassed and heated in a microwave oven for 30 minutes at 150 0C. The solvent was filtered through a pad of celite, water (60 ml_) was added and the product was extracted with EtOAc (3 x, 30 ml_). The combined organic extracts were dried over Na2SO4 (sodium sulfate), and the solvent removed to provide crude 4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol-2-one which was used without further purification.

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-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; WYETH; WO2009/111260; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 40197-20-4, name is 5-Bromo-1H-benzo[d]imidazole-2-carboxylic 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. name: 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid

[0055] N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg),and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight.A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring atroom temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure.The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. Themixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collectedby filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

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

Reference:
Patent; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; (29 pag.)EP3231424; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 24155-42-8, A common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, molecular formula is C11H10Cl2N2O, 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 5 2-[[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:2) 3.2 g of 2-Chloromethylquinoline hydrochloride (0.015 mol) (commercially available), 3.85 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol), 14.8 g sodium hydroxide (0.37 mol) in 25 ml of water, 0.25 g of benzyltrimethylammonium chloride and 40 ml of tetrahydrofuran are reacted in a manner as described in Example 1. After work up, the oily product (6.4 g) is dissolved in 150 ml of ether, charcoaled and then etheral hydrochloric acid is added to the clear solution while stirring. The precipitated hydrochloride (5.8 g) is filtered off, washed with ether and hexane and recrystallized from acetonitrile; m.p. 148-149 C. The following additional products of formula D or E are obtained by the procedure of Example 1 by reacting the unsubstituted or substituted 1-phenyl-2-(1H-imidazol-1-yl)ethanol of formula A with the unsubstituted or substituted 2-chloromethylquinoline of formula B or the unsubstituted or substituted 4-chloromethylquinoline of formula C. The substituents apply to the respective formulae.

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4282230; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1008361-65-6, name is 5-Bromo-6-methoxy-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 1008361-65-6, Product Details of 1008361-65-6

Compound 5-bromo-6-methoxy-1H-benzimidazole 60d (430.0 mg, 1.9 mmol), triethylamine (383.0 mg,3.8 mmol) and 4-dimethylaminopyridine (23.0 mg, 0.2 mmol)With tetrahydrofuran (15.0 mL)After mixing, di-tert-butyl dicarbonate (585.0 mg, 2.9 mmol) was added at room temperature, and the reaction was carried out at 45 C for 12 hours.The reaction solution was diluted with methylene chloride (100 mL) and washed with brine. The organic phase is dried over anhydrous sodium sulfate and filtered to dissolve to give a mixture of 1-t-butoxy acyl-5-Bromo-6-methoxy-benzimidazole 60e and 3-tert-butoxycarbonyl-5-bromo-6-methoxy-benzimidazole 61e (450.0 mg,1.4 mmol, white solid), yield 73%.

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-Bromo-6-methoxy-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Tianyinjianhua Pharmaceutical Technology Co., Ltd.; Kong Xianglong; Zhou Chao; Zheng Zhixiang; (105 pag.)CN109020957; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 86718-07-2,Some common heterocyclic compound, 86718-07-2, name is Ethyl 4-(1-Imidazolyl)benzoate, molecular formula is C12H12N2O2, 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 2 N-(4-Methoxy-3-(4-methyl-1-piperazinyl)phenyl)-4-(imidazol-1-yl) benzamide Ethyl 4-(imidazol-1-yl)benzoate (0.5 g, 2.3 mmol) was heated at reflux in 5N HCl (40 ml) for 1 h, evaporated to dryness under reduced pressure and the resulting white solid dried in vacuo to afford 4-(imidazol-1-yl)benzoic acid This was suspended in dry toluene (40 ml) and thionyl chloride (2 ml) added under argon. The mixture was heated to reflux for 1.5 h and then evaporated to dryness under reduced pressure. The oil was dissolved in dichloromethane under argon and 4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine (551 mg, 2.3 mmol) was added followed by triethylamine (2 ml). The mixture was stirred at room temperature under argon for 2 h and then partitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml), and the organic extracts dried (sodium sulphate). The organic solution was filtered, evaporated to dryness under reduced pressure and purified by column chromatography (silica, chloroform/methanol 5-10%) to afford the amide (809 mg, 90%) which was crystallized from methanol diethyl ether as the oxalate salt. 1H NMR (CDCl3) (free base) delta: 2.38 (3H, s), 2.66 (4H, bm), 3.15 (4H, bm), 3.90 (3H, s), 6.87 (1H, d), 7.29 (2H, m), 7.37 (1H, s), 7.52 (2H, d), 7.86 (1H, s), 7.93 1H, s), 8.01 (2H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(1-Imidazolyl)benzoate, its application will become more common.

Reference:
Patent; SmithKline Beecham p.l.c.; US5834471; (1998); 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. 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, A new synthetic method of this compound is introduced below., Product Details of 53484-15-4

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-(tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoic acid (2.35 g, 9.47 mmol, 1.00 equiv) in CH3CN/toluene (70/12 mL), 5-bromo- l-methyl- lH- benzo[d] imidazole (2 g, 9.48 mmol, 1.00 equiv), Pd(PPh3)4 (548 mg, 0.47 mmol, 0.05 equiv), sodium carbonate (0.4M, 50 mL, 2.00 equiv). The resulting solution was stirred for 18 h at 90C. After cooled to room temperature, the reaction mixture was poured into 50 ml of water. The mixture was washed with 2×100 mL of ethyl acetate and the aqueous layer was collected. The pH value of the solution was adjusted to 4 with hydrochloric acid (IN). The solids were collected by filtration and dried under vacuum. This resulted in 2 g (84%) of the title compound as a white solid, which was dried under vacuum. LC- MS (ES, m/z): 253 [M+H]+

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; FORMA THERAPEUTICS, INC.; BAIR, Kenneth, W.; LANCIA, David, R.; LI, Hongbin; LOCH, James; LU, Wei; MARTIN, Matthew, W.; MILLAN, David, S.; SCHILLER, Shawn, E.r.; TEBBE, Mark, J.; WO2014/164749; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, These common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

General procedure: A mixture of acid 7b (or 7c) (1.3 equivalents), 1-hydroxybenzotriazole (1.3 equivalents), andN,N?-dicyclohexylcarbodiimide or 1,1?-carbonyldiimidazole (1.3 equivalents) was dissolved in dryDMF. Et3N (2.5 equivalents) and amine R2NH2 (one equivalent) were added. The resulting mixture was stirred at room temperature. The reaction progress was monitored by TLC. The solvent wasremoved under reduced pressure. The crude was diluted with water, and NH4OH was added to obtainpH = 10-11. The resulting solid was filtered and washed with water. The product was purified bycolumn chromatography on silica gel.

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 641571-11-1.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem