Month: December 2020

137049-00-4, Name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 137049-00-4, 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.

To a solution of intermediate 2.103 (20. mg, 0.078 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) at 0 C was added 1-methyl-1H-imidazole-4- sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was stirred for 18 h, then diluted with wet DMSO (1 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (18 mg, 57% yield).1H NMR (500 MHz, (0494) Acetonitrile-d3) d 8.61 (s, 1H), 7.73 (s, 1H), 7.69 (dd, J = 11.8, 2.4 Hz, 1H), 7.57 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.26- 7.18 (m, 1H), 3.85- 3.77 (m, 1H), 3.73 (s, 3H), 3.64 (d, J = 12.0 Hz, 1H), 2.67 (t, J = 11.2 Hz, 1H), 2.62- 2.47 (m, 2H), 1.85- 1.76 (m, 1H), 1.59 (qt, J = 12.5, 4.0 Hz, 1H), 1.53- 1.41 (m, 1H); AMM 423.0678 (ESI) m/z [calc for (0495) C16H18ClFN4O3SNa (M+Na)+ 423.0670].

Statistics shows that 1-Methyl-1H-imidazole-4-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 137049-00-4.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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. 104619-51-4

To a solution of 2-((dimethylamino)methyl)-6-nitrophenol (KR-400103) (5.74 mmol, 1.13 g) in methanol (120 mL), PtO2 (0.29 mmol, 0.07 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then stirred under hydrogen atmosphere at ordinary pressure (balloon) for ten hours. Argon wasagain flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a brown solid. The solid was quickly re-dissolved in acetonitrile (120 mL) and di(imidazole-1-yl)methanimine (14.35 mmol, 2.31 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (10:1 chloroform/methanol) provided a colorless oil in an 81% yield. The product of the reduction (2-amino-6-((dimethylamino)methyl)phenol) is air unstable and appropriate measures should be taken to minimize air exposure. An analytical sample of the title compound was isolated by reverse-phase HPLC utilizing a gradient from 0.5-7% acetonitrile in water.

Statistics shows that 104619-51-4 is playing an increasingly important role. we look forward to future research findings about Di(1H-imidazol-1-yl)methanimine.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-83-6, 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. 4887-83-6, name is 7-Methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below.

B. 4-Methylbenzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester A solution of 4-methylbenzimidazole (810 mg, 6.1 mmol), N,N-dimethylaminopyridine (75 mg, 0.6 mmol) and di-tert-butyl dicarbonate (1.54 g, 7.1 mmol) in acetonitrile (20 mL) was stirred at room temperature for 15 min. The solvent was evaporated and the residue was chromatographed (10% ethyl acetate/hexanes) to give 4-methylbenzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (1.35 g, 95%).

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; Hoffmann-La Roche Inc.; US6331640; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1402838-08-7, A common compound: 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

The compound (2-oxo-2-(6-trifluoromethylbenzofuran-5-yl)ethyl) dimethyl phosphate (0207-30) (262 mg, 0.78 mmol, 1.2 eq.)2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (270 mg, 0.65 mmol, 1.0 equiv) andCesium carbonate (847 mg, 2.6 mmol, 4.0 eq.)Mixed in isopropyl alcohol (20 ml),The mixture was stirred at room temperature for 16 hours.After the reaction was completed, quenched with water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a residue which was purified by column chromatography (petroleum ether/ethyl acetate=5/1 to 1/1). The target product (176 mg, yield: 43.3%) was obtained as a yellow gum.

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-(1-Trityl-4-imidazolyl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10394-38-4, A common compound: 10394-38-4, name is 1-Methylbenzoimidazol-5-amine, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 4 1-(3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)-3-(4-((2-((1-methyl-1H-benzo[d]imidazol-5-yl)amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)urea To a solution of Intermediate C1 (155 mg, 80% purity, 0.236 mmol) in DMF (2.0 mL) was added p-TSA.H2O (90 mg, 0.47 mmol) and 1-methyl-1H-benzo[d]imidazol-5-amine (49 mg, 0.33 mmol). The resulting mixture was heated at 60 C. for 16 hr and was then cooled to RT and partitioned between saturated aq. NaHCO3 (40 mL) and EtOAc (25 mL). The organic layer was separated and washed with water (2*50 mL) and brine (50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 0-30% MeOH in DCM, gradient elution) and by preparative HPLC to afford the title compound, Example 4, as a pale pink solid (15 mg, 9%); Rt 1.96 min (Method 2, acidic); m/z 638 (M+H)+, (ES+); 1H NMR delta: 1.30 (9H, s), 2.39 (3H, s), 3.74 (3H, s), 6.42 (1H, s), 6.46 (1H, d), 7.23-7.31 (2H, over-lapping m), 7.37 (2H, d), 7.40 (1H, d), 7.47 (2H, d), 7.55 (1H, dd), 7.61 (1H, dd), 7.77 (1H, br s), 7.83 (1H, d), 7.88 (1H, d), 8.00 (1H, s), 8.07 (1H, d), 8.36 (1H, d), 8.86 (1H, s), 9.18 (1H, s), 9.42 (1H, s).

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-Methylbenzoimidazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOPIVERT PHARMA LIMITED; Duffy, Lorna Anne; King-Underwood, John; Longshaw, Alistair Ian; Murray, Peter John; Onions, Stuart Thomas; Taddei, David Michael Adrien; Williams, Jonathan Gareth; Ito, Kazuhiro; Charron, Catherine Elisabeth; US2015/203475; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 5468-66-6 name is 2-(4-Chlorobenzyl)benzimidazole, 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. 5468-66-6

General procedure: To a 25 mL of Schlenk tube equipped with a Teflon septum were added Imidazoles/Pyrazoles (0.4 mmol, 1.0 equiv) and KF (46.4 mg, 2.0 equiv) under Ar, followed by MeCN (3 mL) with stirring. 2 (0.40 mmol, 1.0 equiv) were added subsequently. After stirring for 12 h, the reaction mixture was concentrated. The residue was purified with silica gel chromatography to provide pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Chlorobenzyl)benzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Mao, Ting; Zhao, Liang; Huang, Yang; Lou, Yue-Guang; Yao, Qiuli; Li, Xiao-Fei; He, Chun-Yang; Tetrahedron Letters; vol. 59; 28; (2018); p. 2752 – 2754;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

101184-08-1, Adding a certain compound to certain chemical reactions, such as: 101184-08-1, name is Methyl 4-(1H-imidazol-1-yl)benzoate, 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 101184-08-1.

EXAMPLE 228 1-(Hydroxymethyl)-4-(1H-imidazol-1-yl)benzene To a mixture of 4-(1H-imidazol-1-yl)benzoic acid methyl ester (prepared as described in U.S. Pat. No. 4,804,662) (1.5 g) in THF (25 ml) at -15 C. was added a solution of 1M LAH/THF (10.4) ml). The mixture was stirred for 1/2 hour and allowed to warm to room temperature. The reaction was quenched by addition of water (0.5 ml), and then diluted with methanol (50 ml) and filtered. Concentration of the filtrate yielded 1.2 g (98%) of 1-(hydroxymethyl)-4-(1H-imidazol-1-yl)-benzene.

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, Methyl 4-(1H-imidazol-1-yl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5206240; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

6775-40-2, These common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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: To a stirred solution ofaldehyde (1 mmol), amine (1 mmol), CCl3CN (2 mmol) in PEG-400 (5mL) at 0 oC, a solution of H2O2 (30%) (3mmol)was added drop wise. Then the reaction mixture was stirred at room temperature for 8-12 h. After completion ofthe reaction (monitored by TLC), the reaction mixture was poured into ice water (50 mL). The solid obtained wasfiltered, washed with water and crude product was purified by column chromatography (silica gel, 60-120 mesh)using hexane/ethylacetate (6:4) as eluent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6775-40-2.

Reference:
Article; Gaddam, Lakshmi Teja; Thata, Sreenivasulu; Adivireddy, Padmaja; Venkatapuram, Padmavathi; Arkivoc; vol. 2019; 6; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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.

Di(imidazole-1-yl)methanimine (17.59 mmol, 2.83 g) was added to a solution of 2-amino-6-chlorophenol (7.03 mmol, 1.01 g) in acetonitrile (40 mL) with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for ten hours. The reaction was then concentrated under reduced pressure and silica gel column chromatography (2:1 hexanes/ethyl acetate) provided a crystalline white solid in a 92% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Di(1H-imidazol-1-yl)methanimine, its application will become more common.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 33016-47-6

[1816] To a stirred solution of starting material benzyl amine (0.99 g, 8.87 mmol) in MeOH (50 mL) under nitrogen inlet at room temperature, was added sodium acetate (0.73 g, 8.87 mmol), 3A molecular sieves (3.0 g) and aldehyde (3.0 g, 8.87 mmol). The resulting solution was stirred at room temperature overnight, followed by addition of NaBH4 (0.67 g, 17.74 mmol), then stirred for 4 hrs and concentrated to dryness, followed by extraction with CH2Cl2-1N NaOH. The combined organic layer was dried over MgSO4, filtered, concentrated to dryness and purified by column chromatography on silica gel, eluting with 2%MeOH-NH3/98%CH2Cl2 to give light yellow oil (3.75 g, 98% yield, MH+=430.2)

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, 33016-47-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhu, Hugh Y.; Njoroge, F. George; Cooper, Alan B.; Guzi, Timothy; Rane, Dinanath F.; Minor, Keith P.; Doll, Ronald J.; Girijavallabhan, Viyyoor M.; Santhanam, Bama; Pinto, Patrick A.; Vibulbhan, Bancha; Keertikar, Kartik M.; Alvarez, Carmen S.; Baldwin, John J.; Li, Ge; Huang, Chia-Yu; James, Ray A.; Bishop, W. Robert; Wang, James J-S; Desai, Jagdish A.; US2003/229099; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem