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, Quality Control of Methyl 1H-imidazole-5-carboxylate

/V-chlorosuccinimide (0.318 g, 2.4 mmol) was added to a stirred solution of methyl 1 H-imidazole-4-carboxylate (0.300 g, 2.4 mmol) in CH3CN (16 mL). The reaction mixture was stirred for 12 h in the dark and then concentrated. The white residue was taken up in EtOAc, satd. aqueous Na2S (10 mL) was added and the solution was stirred for 15 min. The organic layer was isolated, dried (Na2SO4), concentrated and the crude product was purified by column chromatography (20-70% EtOAc/hexanes) to afford the title compound (0.061 g, 16%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 11.05 (br. s., 1 H), 7.85 (s, 1 H), 3.81 (s, 3 H). ES-LCMS: m/z 160.9, 162.9 (M+1 ).

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; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 121 -(4-Cyano-2-fluoro-rhenyl)-1 H-imidazole-4-carboxylic acid methyl ester: A mixture of 3,4-difluorobenzonitrile (193 mg), 1 H-imidazole-4-carboxylic acid methylester (160 mg), and potassium carbonate (150 mg) in N-methyl-2-pyrrolidinone (4mL) is heated to 15000 for 30 mm in a microwave oven. After cooling to room temperature, the reaction mixture is diluted with water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined extracts are dried over MgSO4 and concentrated in vacuo. The residue is triturated with t-butyl methylether, filtered off, and dried to give the title compound. LC (method 4): tR = 0.78 mm; Mass spectrum (ESI): mlz = 246 [M+H]

The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; NOSSE, Bernd; ECKHARDT, Matthias; HIMMELSBACH, Frank; LANGKOPF, Elke; ASHWEEK, Neil J.; HARRIOTT, Nicole; WO2014/19967; (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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H6N2O2

A solution of [1H-IMIDAZOLE-4-CARBOXYLIC] acid methyl ester (1.0 g, 7.93 mmol) in [N, N] dimethylformamide at [25 oC] was treated with triethylamine (2.2 mL, 15.86 mmol) and triphenylmethylchloride (2.43 g, 8.72 [MMOL).] The reaction was stirred at [25 oC] for 8 h and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with water, a IN aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60,230- 400 mesh, 50: 50 ethyl acetate/petroleum ether) afforded 1-trityl-1H-imidazole-4- carboxylic acid methyl ester (2. [88] g, 98.6%) as a white foam

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 17325-26-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17325-26-7, 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. 17325-26-7 name is Methyl 1H-imidazole-5-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 mixture of 4-(bromomethyl)- 1,2-difluorobenzene (10.0 g, 48.3 mmol), 1H-imidazole-4-carboxylate (12.2 g, 96.6 mmol) and potassium hydroxide (5.4 g, 96.6 mmol) in tetrahydrofuran (100 mL) was heated at 70 C for 12H. After cooled, the mixture was filtered and the filtrate was concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 100%) ethyl acetate in petroleum ether) to afford methyl 1-(3,4-difluorobenzyl)-1H-imidazole-4-carboxylate (5.0 g, 41% yield) as a white solid: LCMS (5 to 95% acetonitrile in water + 0.03% trifluoroacetic acid over 1.5 mins) retention time 0.70 min, ESI+ found [M+H] = 252.8.

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

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); 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

Electric Literature of 17325-26-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 17325-26-7 as follows.

A mixture of l ,3-dibromo-5-iodo-2-methoxybenzcnc (C) (Chae, J.; Buchwald, S. L. J. Org. Chem. 2004, 69, 3336-3339) ( 1.6 g, 4.1 mmol), methyl 4-imidazolecarboxylate (0.56 g, 4.4 mmol), cesium carbonate (1.31 g, 4.02 mmol) and 4A molecular sieves (0.88 g) in anhydrous DMF (20 tnL) was stirred under nitrogen for 15 min. Copper(II) trifluoromcthanesulfonate (50 mg, 0.14 mmol) was added and the reaction was stirred at 1 10 0C for 12 h. After cooling, the mixture was filtered and the filtrate was evaporated. The residue was treated with water and extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated. The residue was purified by flash chromatography to give methyl l-(3,5-dibromo-4-methoxyphenyI)-l H-imidazole-4-carboxylate (D) (0.21 g, 13%). 1H NMR delta (ppm)(DMSO-d6): 3.83 (3 H, s), 3.87 (3 H, s), 8.24 (2 H, s), 8.47 (1 H, d, J = 1.38 Hz), 8.62 ( 1 H, d, J = 1.39 Hz).

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; INSTITUTE FOR ONEWORLD HEALTH; JONES, Graham Peter; DOYLE, Kevin James; WO2010/33626; (2010); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 17325-26-7

Step 1: To a stirred mixture of 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (500 mg, 2.2 mmol) from Example36 and methyl 4-imidazole carboxylate (400 mg, 3.3 mmol) in DMF (15 mL) was added K2CO3 (0.9 g, 6.5 mmol).After the mixture was stirred for 3 h at rt, it was partitioned between EtOAc (100 mL) and water (50 mL). The EtOAclayer was separated and washed with water (50 mL) and brine (50 mL), then dried over Na2SO4, filtered, and concentratedunder reduced pressure. The residue was purified by silica gel flash chromatography eluting with 2% MeOH in CH2Cl2to afford methyl 1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-1H-imidazole-4-carboxylate (130 mg, 19%) as a whitesolid. The regiochemistry of the alkylation was determined by 2-dimensional nuclear Overhauser effect (NOE) experiment.1H NMR (300 MHz, DMSO-d6) delta 8.01 (d, J = 0.9 Hz, 1H), 7.98 (d, J = 1.1 Hz, 1H), 7.93 (d, J = 0.9 Hz, 1H), 7.84 (d, J =8.3 Hz, 1H), 7.43 (dd, J = 1.7, 8.3 Hz, 1H), 5.35 (s, 2H), 3.72 (s, 3H), 2.78 (s, 3H). LCMS (ESI) m/z 322 (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; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
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.

To a solution of 2,4-dichloro-5-methylpyridine (1.285 g, 7.93 mmol) in DMF (15 mL) were added methyl 1H-imidazole-4-carboxylate (1 g, 7. 93 mmol) and K2CO3 (5.476 g, 39.68 mmol), and then the mixture was stirred at 100 C. for 6 h. The mixture was cooled and diluted with water, and the solid that formed was removed by filtration and dried to obtain crude product. The crude product was purified by Biotage Isolera (using 50% ethyl acetate in hexane as eluent) to obtain methyl 1-(2-chloro-5-methylpyridin-4-yl)-1H-imidazole-4-carboxylate (0.670 g, 34%). 1HNMR (400 MHz, CDCl3): delta 8.44 (s, 1H), 7.79 (s, 1H), 7.69 (s, 1H), 7.27 1H), 3.94 (s, 3H), 2.28 (s, 3H). LC-MS calcd exact mass 251.05, found m/z 252.1 [M+H]+.

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

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

Related Products 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.

Preparation 121 1-Trityl- 1H-imidazole-4-carboxylic acid methyl ester Add triethylamine (1.88 mL, 13.48 mmol) to a mixture of methyl-4-imidazolecarboxylate (1.0 g, 7.93 mmol) and triphenylmethyl chloride (2.43 g, 8.72 mmol) in anhydrous acetonitrile (25 mL) over 10 min at room temperature and stir overnight. Quench with water and extract with ethyl acetate (3*). Combine the organic layers, wash with 1N hydrochloride solution, water, saturated aqueous sodium bicarbonate solution and brine sequentially, dry over sodium sulfate, and concentrate to provide the title compound 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol).

Statistics shows that Methyl 1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 17325-26-7.

Reference:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl 1H-imidazole-4-carboxylate (500?mg, 3.96?mmol, 1.0 equiv.) was suspended in dry THF (30?mL). Sodium hydride (60% in mineral oil, 238?mg, 5.95?mmol, 1.5 equiv.) was added at 0?C. After 0.5?h of stirring, Hoffer’s chloro sugar (2.29?g, 5.95?mmol, 1.5 equiv.) was added in three portions over 1?h. The reaction mixture was stirred at ambient temperature overnight, and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (100?mL) and washed with water (3?*?25?mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. After purification by column chromatography (cyclohexane:ethyl acetate 2:1???ethyl acetate), compound 6 was obtained as a white solid (965?mg, 2.02?mmol, 51%). HRMS ESI m/z: [M?+?Na]+ 501.1649 (calcd. 501.1638). Elemental analysis (%): found: C 65.1, H 5.4, N 5.8; calcd. for C26H26N2O7: C 65.3, H 5.5, N 5.9. 1H NMR (400?MHz, CDCl3), delta/ppm: 7.94-7.90 (m, 2H, Tol), 7.89-7.85 (m, 2H, Tol), 7.76 (d, 1.4?Hz, 1H, H5), 7.70 (d, 1.4?Hz, 1H, H2), 7.28-7.21 (m, 4H, Tol), 6.13 (dd, 8.1?Hz, 5.6?Hz, 1H, H1′), 5.65 (dt, 6.1?Hz, 2.4?Hz, 1H, H3′), 4.62 (d, 3.7?Hz, 2H, H5′, H5″), 4.58 (td, 3.7?Hz, 2.4?Hz, 1H, H4′), 3.83 (s, 3H, OCH3), 2.75 (ddd, 14.2?Hz, 5.7?Hz, 2.4?Hz, 1H, H2′), 2.64 (ddd, 14.2?Hz, 8.1?Hz, 6.2?Hz, 1H, H2″), 2.42 (s, 3H, CH3), 2.40 (s, 3H, CH3). 13C NMR (101?MHz, CDCl3), delta/ppm: 166.1 (C=O (Tol)), 165.8 (C=O (Tol)), 162.8 (C=O), 144.6 (Tol), 144.2 (Tol), 136.2 (C2), 134.4 (C4), 129.7 (Tol), 129.6 (Tol), 129.3 (Tol), 129.3 (Tol), 126.5 (Tol), 126.2 (Tol), 122.5 (C5), 86.6 (C1′), 83.1 (C4′), 74.8 (C3′), 63.8 (C5′), 51.6 (OCH3), 39.6 (C2′), 21.7 (CH3), 21.6 (CH3).

The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sandmann, Nikolas; Defayay, Denise; Hepp, Alexander; Mueller, Jens; Journal of Inorganic Biochemistry; vol. 191; (2019); p. 85 – 93;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem