Tag: M.W=100-200

Some common heterocyclic compound, 4238-71-5, name is 1-Benzyl-1H-imidazole, molecular formula is C10H10N2, 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. Computed Properties of C10H10N2

1 mol of the compound III obtained in the step (1)1 mol of benzyl chloride was dissolved in THF (tetrahydrofuran)Heated to reflux 12h,The above solution was spin-dry with a rotary evaporator,Then using 3: 1 CH 2 Cl 2 and CH 3 OH as the eluent for chromatographic separation,Obtained pale yellow oily liquid, which is Compound II;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4238-71-5, its application will become more common.

Reference:
Patent; Jiangsu Atomic Medical Institute; Lin Jianguo; Lv Gaochao; Qiu Ling; Guo Liubin; Yang Hui; Wang Tengfei; (17 pag.)CN104650155; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33543-78-1, 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. 33543-78-1 name is Ethyl 1H-imidazole-2-carboxylate, 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 the required amine (0.20 mmol; 2 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is quenched by the addition of a sat. aq. KH2P04 solution and the reaction mixture is stirred at rt for 20 h. The reaction mixture is concentrated under reduced pressure and purification of the residue gives the desired product. Starting from the compound of Preparation R and ethyl imidazole-2-carboxylate and proceeding in analogy to Procedure AQ, the title compound was obtained, after purification by prep-HPLC (basic conditions), as an amorphous solid (22percent yield).MS (ESI, m/z): 340.10 [M+H+].

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); 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. 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H6N2O2

HOBt (3.7 g) and WSC (4.6 g) were successively added to a suspension of 2-methylimidazole-4-carboxylic acid (2.0 g) in acetonitrile (150 mL), and the mixture was stirred at room temperature for 20 minutes. To this reaction solution was added a solution of tert-butyl 4-[(2-hydroxyethyl)amino]piperidine-1-carboxylate (4.7 g) obtained in Example 38a) and triethylamine (8.0 mL) in acetonitrile (50 mL), and the mixture was stirred at room temperature for 15 hours. After acetonitrile was distilled off under reduced pressure, chloroform (100 mL) and water (100 mL) were added to the residue. An organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with a basic silica gel column (ethyl acetate: ethanol = 5:1) to obtain the title compound (1.0 g, 18%) as a colorless oil. NMR (200 MHz, CDCl3) delta: 1.47 (9H, s), 1.84 (4H, bs), 2.37 (2H, bs), 2.78 (2H, bs), 3.82 (4H, bs), 4.27 (3H, bs), 7.31 (1H, bs).

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 1457-58-5.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1564213; (2005); 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1H-Imidazole-4,5-dicarboxylic acid

Into a 100mL round bottom flask, successively added the 1-hydimidazole-4, 5-dicarboxylic acid (600 mg, 1eq, 3.84mmol), thionyl chloride (1.81mL, 6.5eq, 24.8mmol), ultra-dry dimethylformamide (DMF) (0.15mL, 0.5eq, 1.92mmol) and 5mL of toluene, refluxed at 90 C for 16 h. After the reaction, cooling, by using too much toluene in the reaction solution with straw, dissolved in thionyl chloride and DMF aspiration, toluene washed twice and then obtained crude product (compound 1), without further purification directly use for the next step.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Xu Zhongliang; Wang Heyao; Cai Mengxin; (31 pag.)CN106892871; (2017); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

The ethyl 1-(4-chloro-1-oxo-2-indanyl)-imidazole-2-carboxylate can be prepared as in Example 1 for the preparation of ethyl 1-(5-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate but starting with 2.8 g of ethyl imidazole-2-carboxylate, 0.6 g of 80percent sodium hydride, 6.4 g of 2-bromo-4-chloro-1-indanone and a total of 80 ml of anhydrous dimethylformamide. After silica gel chromatography with a dichloromethane-ethyl acetate mixture (80-20 by volume), 1.85 g of ethyl 1-(4-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate are obtained Rf=0.3, thin-layer chromatography on silica gel; solvent: dichloromethane-ethyl acetate (80-20 by[volume)]. The 2-bromo-4-chloro-1-indanone can be prepared in the following manner:

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-83-6, name is 7-Methyl-1H-benzo[d]imidazole, 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. Recommanded Product: 4887-83-6

4-Methyl-1 H-benzimidazole (328 mg; APAC) was dissolved in DCM (7 ml_), di-te/f-butyl dicarbonate (0.634 ml.) was added and the solution was stirred at RT for 18 hr. The solvent was evaporated to give the title compound (575 mg) as a yellow oil. It was used without further purification, m/z [M+H]+: 233.2. Retention time 1.18 min (LC/MS method 3

The synthetic route of 4887-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16265-04-6, name is 2-Chloro-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 16265-04-6, HPLC of Formula: C3H3ClN2

Intermediate 77 Sodium hydride (60%> in mineral oils, 468 mg, 11.7 mmol) was added to 2-chloro-lH- imidazole (800 mg, 7.8 mmol) in THF (24 mL) at 0 C. The mixture was stirred at rt for 10 min. Then 2-(trimethylsilyl)ethoxymethyl chloride (2 mL, 11.7 mmol) was added at 0 C and the mixture was stirred for 2 h. The mixture was diluted with sat. sol. NH4C1 and extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in Heptane 0/100 to 50/50). The desired fractions were collected and the solvents concentrated in vacuo to yield 1-77 (1.52 g, 89%).

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; JANSSEN PHARMACEUTICA NV; VAN GOOL, Michiel, Luc, Maria; ALCAZAR-VACA, Manuel, Jesus; ALONSO-DE DIEGO, Sergio-Alvar; DE LUCAS OLIVARES, Ana, Isabel; (105 pag.)WO2016/87487; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4857-06-1, name is 2-Chloro-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 4857-06-1, COA of Formula: C7H5ClN2

Step 1: 1.00 g, 6.5 mmol of 2-chlorobenzimidazole,Dissolved in 15 mL of tetrahydrofuran,Add 288mg, 7.2mmol 60% sodium hydride,After stirring for half an hour, 0.60 mL, 9.8 mmol of methyl iodide was added.The mixture was stirred at room temperature for 2 hours.Then add water, extract with ethyl acetate, wash with water, wash with brine, dry, concentrate, and then purify by column chromatography.1-Methyl-2-chlorobenzimidazole was obtained, a pale yellow liquid, 0.95 g, yield 88%.

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; Guangzhou Baiting Pharmaceutical Technology Co., Ltd.; Wu Zhong; Li Jingrong; (16 pag.)CN108997394; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, 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: C9H7N3O2

Benzyl bromide (712 muIota_, 6 mmol) and 4-nitrophenylimidazole (222 mg, 1 .2 mmol.) were stirred in 10 ml of anhydrous THF under reflux for 45 h and under inert atmosphere. The precipitate was then filtered, washed with THF and dried under reduced pressure to give 393 mg (91 %) of 1-benzyl-3-(4-nitrophenyl)imidazolium bromide (Example 1) as an off white powder. 1H NMR (DMSO-d6, 400.13 MHz): delta 10.37 (t, 1 H, J = 1.5 Hz, N-CH-N), 8.57 (1 H, m, H(imidazolium backbone)), 8.55 (2H, m, H(nitrobenzyl)), 8.19 (1 H, m, H(imidazolium backbone)), 8.17 (2H, m, H(nitrophenyl)), 7.64-7.58 (2H, m, Hm(benzyl)), 7.52-7.43 (3H, m, Hp + Ho(benzyl)), 5.61 (2H, s, CH2). 13C NMR (DMSO-d6,100.16 MHz): delta 147.7 (carbene), 139.5, 134.4, 129.1 , 129.0, 128.9, 125.7, 123.7, 123.2, 121.8, 52.7 (CH2). MS (ES+) calcd for (M-Bn+H)+ 190.1 (100%), 191 .1 (1 1 %) (M-Br)+: 280.1 (100%), 281 .1 (18.7%), (2M-Br)+: 639.1 (100%), 641.1 (95%), 640.1 (36%), 642.1 (36%) Found (M- Bn+H)+ 190.0 (100%) (M-Br)+: 280.1 (100%), 280.8 (18.9%), (2M-Br)+: 639.0 (95 %), 641 .0(100%)

The synthetic route of 2301-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CHU NANTES; UNIVERSITE DE NANTES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S); FAIVRE-CHAUVET, Alain; RAJERISON, Holisoa; GESTIN, Jean-Francois; WO2013/171224; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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. Formula: C5H6N2O2

a) 3-(1,2,3,4-Tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 1 ,2,3,4-tetrahydro-1-naphthol (CASNo. 529-33-9, 1.00 g, 6.74 mmol), which can be prepared as described in Ollivier, R.; et al. Journal of Medicinal Chemistry, 1997, 40, 952-960, in THF (60 ml_), at 0 0C is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 0.85 g, 6.74 mmol) and triphenylphosphine, followed by diisopropyl azodicarboxylate (1.36 g, 6.74 mmol). The cooling bath is then removed. After 16 hours, the solvent is evaporated in vacuo and the residue is purified by silica gel flash chromatography (elution with ethyl acetate) to give a partially purified product, which is dissolved in ethyl acetate and extracted with 1 M aqueous HCI. The aqueous layer is basified to a pH of ca. 9 with 2M aqueous NaOH, and then extracted three times with dichloromethane. The organic layers are combined, dried with MgSO4, filtered, and concentrated to furnish 3-(1 ,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 257.2 (M+H)+. The HNO3 salt of the title compound is prepared by dissolving the free base in methanol, followed by treatment with an excess of a 1 :1 solution of HNO3-H2O. Concentration and trituration with diethyl ether and methanol, provides the nitric acid salt of 3-(1 ,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4- carboxylic acid methyl ester; 1H NMR (400 MHz, DMSO-Cf6) delta ppm 1.66 – 1.87 (m, 2 H), 2.11 – 2.33 (m, 2 H), 2.81 (dt, J=17.2, 6.5 Hz, 1 H), 2.93 (dt, J=17.2, 6.0 Hz, 1 H), 3.87 (s, 3 H),6.33 (t, J=5.9 Hz, 1 H), 6.99 (d, J=7.6 Hz, 1 H), 7.10 – 7.21 (m, 1 H), 7.21 – 7.35 (m, 2 H),8.34 (S1 1 H), 8.58 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17325-26-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem