Category: 17325-26-7

Adding a certain compound to certain chemical reactions, such as: 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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 17325-26-7, Product Details of 17325-26-7

EXAMPLE 1 12-{2-[4-chloro-3-(methyloxy)phenyl]-1 H-imidazol-4-yl}-N,N-dimethyl-1-[2-(m1 H-benzimidazole-5-carboxamidestep 1 s epstep 6Step 1. methyl 1 -({[2-(trimethylsilyl)ethyl]oxy}methyl)-1 /-/-imidazole-4-carboxylate: A mixture of methyl 1 H-imidazole-4-carboxylate (2.80 g, 22.20 mmol), {2-[(chloromethyl) oxy]ethyl}(trimethyl)silane (5.1 1 mL, 28.9 mmol) and potassium carbonate (7.67 g, 55.5 mmol) in DMF (20 mL) was heated at 80C for 24 hours. Reaction showed -1 :1 starting materiahdesired product by TLC. The reaction was cooled to room temperature, diluted with ethyl acetate and water, and layers were separated. Organics were washed with brine, concentrated and purified by Biotage (50 g silica column, 10-75% E/H, 20 min.; 75%, 10 min.). Clean fractions were combined, concentrated and dried to give the title compound as a light yellow oil (2.46 g, 45%). 1H NMR (400 MHz, DMSO-d6) delta 8.02 (d, J 1.26 Hz, 1 H), 7.92 (d, J = 1 .26 Hz, 1 H), 5.37 (s, 2H), 3.74 (s, 3H), 3.44 – 3.52 (m, 2H), 0.80 – 0.88 (m, 2H), -0.03 (s, 9H); MS (m/z) 257.0 (M+H)+.

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17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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: 17325-26-7

Step B: Sodium hydride (519 mg, 21.6 mmol) was added to a cooled (0 C.) solution of the compound prepared in Step A (4.03 g, 14.4 mmol) and methyl 4-imidazolecarboxylate (2.0 g, 16 mmol) in 100 mL of DMF. The reaction mixture was allowed to warm to rt. After 16 h at rt no desired product was observed, and the reaction mixture was heated to 50 C. for 163 h. Although a significant amount of the starting material (the mesyl intermediate) remained, the reaction mixture was diluted with 150 mL of diethyl ether, washed with water (5×150 mL) and brine (1×150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by MPLC (silica gel, 0-60% EtOAc/hexanes) afforded the desired product and recovered starting material. ESI-MS calculated for C15H23N3O4: 309.36. found 310 (M+H).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 1H-imidazole-5-carboxylate

c) 3-{[(2-Bromo-benzyl)-methyl-carbamoyl]-methyl}-3H-imidazole-4-carboxylic acid methyl ester; To a solution of N-(2-bromo-benzyl)-2-hydroxy-N-methyl-acetamide (1.02 g, 3.95 mmol) in THF (40 mL) at 0 0C is added triphenylphosphine (1.15 g, 4.36 mmol), methyl 4- imidazolecarboxylate (CASNo. 17325-26-7, 0.50 g, 3.96 mmol) and diisopropyl azodicarboxylate ( 0.85 mL, 4.36 mmol). The reaction is permitted to warm to room temperature and allowed to stir 18 hours. The reaction is then adsorbed directly onto silica gel and submitted to silica gel flash chromatography (diethylamine-methanol- dichloromethane, 1 :3:96) to provide 3-{[(2-bomo-benzyl)-methyl-carbamoyl]-methyl}-3H- imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 366.2, 368.2 (M+H)+.

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

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

Application of 17325-26-7, A common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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.

lambda/-bromosuccinimide (0.900 g, 5.0 mmol) was added to a stirred solution of methyl 1 H-imidazole-4-carboxylate (0.630 g, 5.0 mmol) in CH3CN (50 mL). The reaction mixture was stirred for 12 h in the dark and then concentrated in the presence of silica gel. The absorbed crude material was purified by column chromatography (20- 100% EtOAc/hexanes) to afford the title compound (0.708 g, 70%) as a white solid. 1H NMR (400 MHz, DMSOd6) delta ppm 1 1.00 (br. s., 1 H), 7.81 (s, 1 H), 3.81 (s, 3 H). ES-LCMS: m/z 204.9, 206.9 (M+1 ).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); 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. category: imidazoles-derivatives

d) 3-(3,3-Difluoro-2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 3,3-difluoro-2,2-dimethyl-indan-1-ol (388 mg, 1.96 mmol) in THF (16 ml.) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 370 mg, 2.94 mmol), and triphenylphosphine (770 mg, 2.94 mmol). The reaction is cooled to 0 0C and di-f-butyl azodicarboxylate (670 mg, 2.94 mmol) is added. The reaction is placed at room temperature and permitted to stir for six hours and then is heated to 40 0C overnight. The next day the reaction mixture is cooled to 0 0C and quenched with 4 N HCI in dioxane (5 ml_, 20 mmol) and stirred for 30 minutes. The reaction is concentrated to near dryness and diluted with ethyl acetate. The organic layer is extracted three times with 1 N aqueous HCI. The aqueous extracts are combined, neutralized with Na2CO3, and extracted three times with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1:5) to furnish 3-(3,3-difluoro-2,2-dimethyl-indan-1-yl)-3H- imidazole-4-carboxylic acid methyl ester. MS: (ESI) m/z 307.0 (M+H)+; 1H NMR (400 MHz, CDCI3) delta ppm 0.87 (d, J=2.5 Hz, 3 H), 1.33 (d, J=3.0 Hz, 3 H)1 3.96 (s, 3 H), 6.43 (d, J=2.8 Hz, 1 H), 7.17 (s, 1 H), 7.30 – 7.37 (m, 1 H), 7.56 – 7.64 (m, 2 H), 7.69 – 7.76 (m, 1 H), 7.85 (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

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

To a solution of methyl 1H-imidazole-4-carboxylate (3.78 g, 30 mmol) in anhydrous THF (60 mL) was added sodium hydride (0.72 g, 30 mmol). The solution was then stirred at room temperature for 1 h before addition of 2-bromoacetonitrile (4.2 g, 35 mmol). The reaction was stirred at room temperature for 2 h before being concentrated in vacuo. The crude residue was purified on silica gel (petroleum ether:ethyl acetate=3:1) to afford the desired product (2.48 g, 50% yield). MS m/z: 166 [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 17325-26-7, its application will become more common.

Reference:
Patent; Albrecht, Brian K.; Bellon, Steven F.; Gehling, Victor S.; Harmange, Jean-Christophe; LeBlanc, Yves; Liang, Jun; Magnuson, Steven; Tsui, Vicki; Zhang, Birong; US2015/65522; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17325-26-7,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.

d) 3-(2,2-Dimethyl-4-oxo-1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one (2.87 g, 13.88 mmol) and methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 1.25 g, 9.72 mmol) in THF (80 ml.) at 0 0C is added triphenylphosphine (3.68 g, 13.88 mmol) and dimethyl azodicarboxylate (40% in toluene, 5.14 ml_, 13.88 mmol) and the cooling bath is removed. After 15 hours, the mixture is concentrated and the resulting residue is dissolved in ethyl acetate (250 ml.) and is extracted five times with 1 M aqueous HCI (40 mL portions). The acidic aqueous phases are cooled to 0 0C and the pH is adjusted to ca. 12 with 4M aqueous NaOH at 0 0C. The aqueous phase is then extracted three times with dichloromethane. The combined organic layers are dried over MgSO4 and filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (dichloromethane-methanol, 49:1) to give 3-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4- carboxylic acid methyl ester; MS: (ESI) m/z 299.0 (M+H)+; 1H NMR (400 MHz, CDCI3) delta ppm 0.97 (S, 3 H), 1.15 (s, 3 H), 2.63 (d, J=16.8 Hz, 1 H), 2.74 (d, J=16.8 Hz, 1 H), 3.93 (s, 3 H), 6.79 (s, 1 H), 7.02 (d, J=7.6 Hz, 1 H), 7.35 (s, 1 H), 7.47 (t, J=7.6 Hz, 1 H), 7.55 (td, J=7.6, 1.5 Hz, 1 H), 7.86 (s, 1 H), 8.13 (dd, J=7.6, 1.5 Hz, 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 Methyl 1H-imidazole-5-carboxylate, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H6N2O2

To a solution of N-(2,3-dihydrobenzofuran-5-yl)-4-iodopyridin-2-amine (300 mg, 0.88 mmol) in DMF (3 mL) was added methyl 1H-imidazole-4-carboxylate (167 mg, 1.3 mmol), potassium phosphate (564 mg, 2.6 mmol) and L-Proline (20 mg, 0.17 mmol) under a nitrogen atmosphere. The reaction mixture was purged with nitrogen for 10 min, then copper iodide (33 mg, 0.17 mmol) was added, and then the reaction mixture was stirred for 15 h at 140 C. in a sealed glass tube. Reaction mixture was cooled and filtered through Celite, and the filtrate was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and evaporated under reduced pressure, and the residue was purified by gradient column chromatography using ethyl acetate in n-hexane as eluent to afford methyl 1-(2-((2,3-dihydrobenzofuran-5-yl)amino)pyridin-4-yl)-1H-imidazole-4-carboxylate as a yellow semi-solid (0.10 g, 17%). LC-MS calcd exact mass 336.12, found m/z 337.2 [M+H]+.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17325-26-7, These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-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.

To a solution of 5-fluoro-indan-1-ol (0.293 g, 1.925 mmol) and methyl 4- imidazolecarboxylate (CASNo. 17325-26-7, 0.163 g, 1.290 mmol) in.THF (10 mL) at 0 0C is added pMe2NPhP(Ph)2 (0.619 g, 1.925 mmol) and diisopropyl azodicarboxylate (94%, 0.414 g, 1.925 mmol). After 1 hour the mixture is warmed to room temperature and after 18 hours it is diluted with ethyl acetate and extracted with 1M aqueous HCI. The extracts are cooled to 0 0C, and the pH is adjusted to ca. 9 with ice-cold 4M aqueous NaOH. The basic aqueous phase is extracted three times with dichloromethane, and the combined organic phases are dried over magnesium sulfate, filtered through a cotton plug, and concentrated. The resulting residue is purified by silica gel flash chromatography (elution with dichloromethane- methanol, 1 :0 to 99:1 to 49:1) to afford 3-(5-fluoro-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 261.0 (M+H) The HCI salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1 N HCI in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCI salt of 3-(5-fluoro-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; 1H NMR (400 MHz1 CDCI3) delta ppm 2.06 – 2.20 (m, 1 H), 2.71 – 2.85 (m, 1 H), 2.87 – 3.00 (m, 1 H), 3.00 – 3.14 (m, 1 H), 3.87 (s, 3 H)1 6.47 (dd, J=7.7, 4.7 Hz, 1 H), 6.88 – 6.97 (m, 1 H), 7.01 (dd, J=8.6, 2.3 Hz1 1 H), 7.16 (dd, J=8.6, 5.1 Hz, 1 H), 7.19 (s, 1 H)1 7.77 (s, 1 H).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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 17325-26-7, Application In Synthesis of Methyl 1H-imidazole-5-carboxylate

Methyl 4-imidazolecarboxylate (1.09 g, 8.62 mmol) was slowly added to a suspension of sodium hydride (60% dispersion in oil, 0.52 g, 13 mmol) in DMF (40 mL). The mixture was heated to 80 C. and stirred at this temperature for 1 hour. A solution of compound 8 (3.61 g, 12.90 mmol) in DMF (20 mL) was added dropwise to the reaction mixture at this temperature and the reaction mixture stirred a further 12 hours at 80 C. The cooled mixture was filtered, the volatiles removed in vacuo and the residue purified by column chromatography on silica gel (100% n-heptane to 100% EtOAc) to yield compound 10 (0.91 g, 34%) as a yellow semi solid first LC-MS (MH+): m/z=311.3, tR (min,)=1.15 then compound 9 (1.38 g, yield: 51%) as a yellow solid LC-MS (MH+): m/z=311.3, tR (minutes)=1.16.

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; H. Lundbeck A/S; US2012/129836; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem