Category: 37619-25-3

Application of 37619-25-3, A common heterocyclic compound, 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, molecular formula is C9H8N2O2, 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.

A solution of BnBr (1.11 g, 6.6 mmol) in DMF (1.5 mL) was added dropwise to a solution of the compound Int-40 (880 mg, 5 mmol) in DMF (10 mL) at 0~5 C. The reaction was allowed to warm to room temperature and was stirred for 15 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over NaiSCri and concentrated under reduced pressure. The crude product was purified by column chromatography (hexanes/ ethyl acetate:3/l) to afford the compound Int-41 (600 mg, 45%) as a yellow solid. NMR (400 MHz, CDCh): d 3.74 (s, 3H), 5.75 (s, 2H), 6.93-6.95 (m, 2H), 7.20-7.24 (m, 3H), 7.28 (t, J = 8.0 Hz, 1H), 7.71 (dd, J = 0.8, 8.0 Hz, 1H), 8.00 (dd, J = 0.8, 8.0 Hz, 1H), 8.07 (s, 1H). ESI-MS (EI+, m/z) : 267.15.

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; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael; ZHANG, Tinghu; FISCHER, Eric; VERANO, Alyssa; HE, Zhixiang; DU, Guangyan; DONOVAN, Katherine; NOWAK, Radoslaw; YUAN, Christine; LIU, Hu; (0 pag.)WO2020/6233; (2020); 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. 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8N2O2

[Step 2] Methyl 6-nitro-1H-benzimidazole-4-carboxylate Methyl 1H-benzimidazole-4-carboxylate (315 mg) was dissolved in conc. sulfuric acid (3 mL), and the solution was stirred on ice bath. A small amount of potassium nitrate (199 mg) was added portion-wise, the solution was stirred at room temperature for 4 hours. The reaction mixture was poured into ice, alkalified with 3N aqueous sodium hydroxide solution under stirring on ice bath, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate. The titled compound (334 mg) was obtained as colorless powder after distilling off a solvent under reduced pressure.

According to the analysis of related databases, 37619-25-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; OTSU, Hironori; EP2746265; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, molecular formula is C9H8N2O2, 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. Recommanded Product: 37619-25-3

Methyl 1H-benzimidazole-4-carboxylate (315 mg) was dissolved in conc. sulfuric acid (3 mL), and the solutionwas stirred on ice bath. A small amount of potassium nitrate (199 mg) was added portion-wise, the solution was stirredat room temperature for 4 hours. The reaction mixture was poured into ice, alkalified with 3N aqueous sodium hydroxidesolution under stirring on ice bath, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentiallywith water and brine, dried over anhydrous magnesium sulfate. The titled compound (334 mg) was obtained as colorlesspowder after distilling off a solvent under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37619-25-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; OTSU, Hironori; EP2746265; (2015); B1;,
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. 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, A new synthetic method of this compound is introduced below., Safety of Methyl 1H-benzo[d]imidazole-4-carboxylate

Methyl 1H-benzo[d]imidazole-4-carboxylate (0.504 g, 2.861 mmol) was dissolved in THF/dioxane (3:2, 50 mL). A 1.0 M solution LiAlH4 in THF (3.00 mL, 3.00 mmol) was added slowly and the reaction was left to stir for 1 hour. The reaction was quenched by successive addition of water (114 muL), 15% NaOH (114 muL) and water (342 muL). The suspension was stirred for 5 minutes and Na2SO4 (3.0 g) was added and the stirring was continued for 10 minutes. The suspension was filtered and the filter cake washed with THF (2 × 15 mL). The combined filtrates were evaporated under reduced pressure to give the title compound (0.356 g, 84%) as a white solid. mp. 159 – 161 C. 1H NMR (300 MHz, CD3OD) delta 8.13 (s, 1H), 7.51 (dd, J = 7.4, 1.7 Hz, 1H), 7.26 (dd, J = 7.3, 1.7 Hz, 1H), 7.21 (dd, J = 7.3, 7.4 Hz, 1H), 5.07 (br s, 2H), 4.98 (s, 3H). 13C NMR (75 MHz, CD3OD) delta 142.2, 139.2, 136.0, 129.5, 123.5, 121.7, 115.5, 61.8.

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:
Article; Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Braeuner-Osborne, Hans; Kristensen, Jesper Langgaard; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3933 – 3937;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-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. COA of Formula: C9H8N2O2

Ste AG2: (1 H-Benzoimidazol-4-yl)-methanolTo a solution of 1 H-Benzoimidazole-4-carboxylic acid methyl ester (Step AG3, 1.0 g, 5.68 mmol) in THF (56.8 mL) under argon was added LiAIH4 (1 M in THF) (6.24 mL, 6.24 mmol), dropwise, causing a yellow coloration and a slight gas evolution. The reaction mixture was stirred at rt for 75 min. The medium was carefully quenched by addition of saturated aqueous NH4CI solution (50 mL). The slurry of aluminium salts was stirred for an hour at rt. The organic supernatant was decanted and the insoluble aluminium salts suspension was extracted with AcOEt (3 x 100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to give a colorless oil (600 mg, 71 %). HPLC/MS (Method A) tR0.64 minute, M+H 149.0 . 1 H NMR (DMSO- cfe) Ppm 4.85 (br. s., 2 H) 5.19 (br. s., 1 H) 7.07 – 7.26 (m, 2 H) 7.48 (d, J=7.34 Hz, 1 H) 8.19 (s, 1 H) 12.35 – 12.64 (m, 1 H).

The synthetic route of 37619-25-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BERST, Frederic; FURET, Pascal; MARZINZIK, Andreas; WO2011/157787; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 37619-25-3, The chemical industry reduces the impact on the environment during synthesis 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Into a 100-mL round-bottom flask, was placed a solution of methyl 1H-1,3- benzodiazole-4-carboxylate (500 mg, 2.84 mmol, 1.00 equiv) in N,N-dimethylformamide (60 mL), potassium carbonate (1.1 g, 7.96 mmol, 3.00 equiv), and (2-chloroethyl)dimethylamine hydrochloride (523.6 mg, 3.64 mmol, 1.00 equiv). The resulting solution was stirred overnight at 60 oC in an oil bath then allowed to cool and diluted with 40 mL of sodium chloride (aq). The resulting mixture was extracted with 2×40 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:2). This resulted in 100 mg (14%) of methyl 1-[2-(dimethylamino)ethyl]-1H-1,3- benzodiazole-4-carboxylate as a solid

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 1H-benzo[d]imidazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); 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. 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 1H-benzo[d]imidazole-4-carboxylate

Step AG2: (1 H-Benzoimidazol-4-yl)-methanolTo a solution of 1 H-Benzoimidazole-4-carboxylic acid methyl ester (Step AG3, 1.0 g, 5.68 mmol) in THF (56.8 mL) under argon was added LiAIH4 (1 M in THF) (6.24 mL, 6.24 mmol), dropwise, causing a yellow coloration and a slight gas evolution. The reaction mixture was stirred at rt for 75 min. The medium was carefully quenched by addition of saturated aqueous NH4CI solution (50 mL). The slurry of aluminium salts was stirred for an hour at rt. The organic supernatant was decanted and the insoluble aluminium salts suspension was extracted with AcOEt (3 x 100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to give a colorless oil (600 mg, 71 %). HPLC/MS (Method A) tR0.64 minute, M+H 149.0 . 1 H NMR (DMSO- d6) Ppm 4.85 (br. s., 2 H) 5.19 (br. s., 1 H) 7.07 – 7.26 (m, 2 H) 7.48 (d, J=7.34 Hz, 1 H) 8.19 (s, 1 H) 12.35 – 12.64 (m, 1 H).

According to the analysis of related databases, 37619-25-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BERST, Frederic; FURET, Pascal; MARZINZIK, Andreas; STAUFFER, Frederic; WO2011/157793; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem