Tag: M.W=100-200

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

Electric Literature of 20271-20-9,Some common heterocyclic compound, 20271-20-9, name is Methyl 5-nitro-1H-imidazole-4-carboxylate, molecular formula is C5H5N3O4, 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 Description 17 (1.24g, 7. 25 mmol) in1 : 1 ethanol : methanol (60 ml) was hydrogenated using 10 % palladium on carbon catalyst under a balloon of hydrogen. After 4 h the reaction mixture was filtered, the filtrate condensed and azeotroped with ethanol. The product was triturated with ethyl acetate and dried to give the title compound as a white solid (0.98 g, 96%).’H NMR (400 MHz, DMSO)8 12.0(1H, brs), 7.32(1H, s), 5.56 (2H, s), 3.70 (3H, s). Mlz (ES+) 142 (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 Methyl 5-nitro-1H-imidazole-4-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; HOLLINGWORTH, Gregory, John; JONES, A., Brian; SPAREY, Timothy, Jason; WO2005/49613; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 93668-43-0,Some common heterocyclic compound, 93668-43-0, name is 2-(1H-Imidazol-1-yl)ethanamine dihydrochloride, molecular formula is C5H11Cl2N3, 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 1.47 g. portion of 1H-imidazole-1-ethanamine dihydrochloride was reacted with 3-chloro-benzo[b]thiophene-2-carbonyl chloride as described in Example 1, giving 0.75 g. of the desired product, m.p. 132-134 C.

The synthetic route of 93668-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4489089; (1984); A;,
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. 154094-97-0, name is 2-(1H-Imidazol-1-yl)ethanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H10ClN3

Example 1 : Synthesis of 2-Cyclopentyl-2-hydroxy-lambda/-[2-(lH-imidazol-l-yl)ethyll-2- phenylacetamide (Compound No. 1) To a solution of the hydrochloride salt of 2-(lH-imidazol-l-yl)ethanamine (0.5 g, 4.50 mmol) in chloroform (10 ml) was added N-methyl morpholine (2.96 ml, 27.02 mmol) and stirred the mixture for 5 to 10 minutes at the room temperature followed by the addition of 2- cyclopentyl-2-hydroxy-2-phenyl acetic acid (0.99 g, 4.5 mmol) and hydroxy benzotriazole (0.60 g, 4.5 mmol) at room temperature. The resulting reaction mixture was stirred for 30-45 minutes followed by the addition of l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and again stirred for over night. The mixture was diluted with water and stirred for 10-15 minutes followed by the addition of dichloromethane. The mixture was stirred for 15-20 minutes. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by preparative column chromatography using 10 % methanol in dichloromethane as eluent to furnish the title compound. Yield: 70 mg.1H NMR (CDCl3)delta: 7.60-7.31 (5H, m), 6.99 (IH, s), 6.99 (IH, s), 6.65 (IH, s), 4.01-4.00 (2H, m), 3.99-3.49 (2H, m), 3.11-3.07 (IH, m), 1.64-1.42 (8H, m).

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 154094-97-0.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2007/77510; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14003-66-8, 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. 14003-66-8, name is 4-Methyl-5-nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Synthesis 90 (E)-4-(2-(5-Nitro-1 H-imidazol-4-yl)vinyl)benzonitrile4-Cyanobenzaldehyde (75 g, 0.57 mol) was heated to 1100C. Once melted, 4-methyl-5- nitroimidazole (15 g, 0.12 mol) and piperidine (5 g, 0.06 mol) were added and heating continued for a further 24 hours. DMF (15 ml.) and IPA (150 mL) were then added and the precipitate filtered from solution and washed with IPA (50 mL) to leave the product as a yellow solid (13.8 g, 49%). mp > 30O0C. deltaH (DMSO-cfe) 7.95 (1H1 s), 7.88 (2H, d, J = 6.8), 7.78 (2H, d, J = 6.8), 7.78 (1H, d, J = 16.8), 7.50 (1 H, d, J = 16.8); IR (cm 1) 2239 (C?N), 1502, 1348 (NO2); MS (m/z) 241.1 (Ci2H9N4O2 (M+1)).

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, 4-Methyl-5-nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMINOX LIMITED; HUMMERSONE, Marc, Geoffery; STEVENS, Malcolm, Francis, Graham; COUSIN, David; WO2010/149968; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 26530-93-8, 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. 26530-93-8, name is 1-Methyl-1H-benzo[d]imidazol-6-amine, This compound has unique chemical properties. The synthetic route is as follows.

3.2 3-{(Z)-1-[(1-methyl-benzimidazol-6-yl)amino]-1-phenylmethylidene}-2-indolinone Prepared from 1-acetyl-3-{1-ethoxy-1-phenylmethylidene}-2-indolinone and 2 equivalents of 6-amino-1-methyl-benzimidazole, melting point 163-165° C., in DMF followed by treatment with 1N sodium hydroxide solution in MeOH. Yield: 54percent of theory; Melting point: 298-300° C.; C23 H18 N4 O; Calc.: C, 75.39; H, 4.95; N, 15.29; Found: 75.16; 5.00; 15.18; Calc.: molar peak M+ =366; Found: molar peak M+ =366.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-benzo[d]imidazol-6-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6043254; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 88704-72-7, A common heterocyclic compound, 88704-72-7, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine hydrochloride, molecular formula is C9H12ClN3, 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 compound 5, 6 or 7 (1 equiv) and the appropriate alkylamine(1.3 equiv) in anhydrous DMF (10 mL/mmol) were added DIEA (3equiv) and PyBOP (1 equiv), and the reaction mixturewas stirred atroom temperature under argon. When the reaction was complete(2 h – 4 h), the solvents were removed under reduced pressure togive a residue that was taken up in CH2Cl2. The solution waswashed with saturated aqueous NaHCO3, then water. The organiclayer was dried over Na2SO4 and then evaporated in vacuo. Purificationby flash chromatography afforded the corresponding amidederivatives 8, 9 or 10 (yield: 40-76%).

The synthetic route of 88704-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paoletti, Julie; Assairi, Liliane; Gelin, Muriel; Huteau, Valerie; Nahori, Marie-Anne; Dussurget, Olivier; Labesse, Gilles; Pochet, Sylvie; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 1041 – 1056;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 67768-61-0, name is 1-Cyclohexyl-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 67768-61-0, HPLC of Formula: C9H14N2

D) 1,1′-Dicyclohexyl-3,3′-methylenediimidazolium diiodide 11 0.0065 mol of diiodomethane (1.741 g; 0.52 ml) and 5 ml of tetrahydrofuran are added to 0.013 mol of cyclohexylimidazole (2.000 g) in an ACE pressure tube. The reaction mixture is stirred at 80 C. for 3 hours. The solid which precipitates is washed repeatedly with a little tetrahydrofuran. The white solid 11 is obtained. Empirical formula: C19H30N4I2 M=568.270 g/mol Yield: 0.891 g (24.1% of theory) Melting point: decomposition at >286 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.45 (s, 2H, NCN); 8.01 (dd, 4H, J=1.6 Hz, NCCN); 6.58 (s, 2H, NC2N); 4.36 (t, 2H, J=11.7 Hz, C of cyclohexyl ring); 2.09 (d, 4H, J=9.7 Hz, C2 of cyclohexyl ring); 1.85 (d, 4H, J=13.3 Hz, C2 of cyclohexyl ring); 1.68 (d, 4H, J=12.3 Hz, C2 of cyclohexyl ring); 1.40 (quart, 4H, J=12.7 Hz, C2 of cyclohexyl ring); 1.23 (t, 4H, J=12.5 Hz, C2 of cyclohexyl ring)

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

Reference:
Patent; BASF SE; TECHNISCHE UNIVERSITAET DRESDEN; US2009/326237; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

326-55-6, name is 6-(Trifluoromethyl)-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. Application In Synthesis of 6-(Trifluoromethyl)-1H-benzo[d]imidazole

Add 0.3mmol 5-trifluoromethylbenzimidazole, 0.009mmol photosensitizer, 0.6m mol sodium hydroxide to a 15ml schlenck tube,After the nitrogen protection was completed, 0.6 mmol of ethyl bromodifluoroacetate and 3 mL of DMF were added with a syringe.Then, it reacted at room temperature for 12 hours under 15 W blue light irradiation.After the reaction, add two medicine spoon column chromatography silica gel (100-200 mesh) to the reaction solution, and remove the solvent by distillation under reduced pressure.The product was purified by column chromatography (petroleum ether / ethyl acetate = 50: 1 as eluent). The material was a yellow liquid with a yield of 73%.

The synthetic route of 326-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Liu Yunkui; Hu Xiaojun; Zhou Bingwei; (10 pag.)CN110483406; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

70631-93-5, name is 5-Methyl-1H-imidazole-2-carboxylic acid, 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. name: 5-Methyl-1H-imidazole-2-carboxylic acid

A mixture of N-cyclopropyl-8-((4-methoxybenzyl)(methyl)amino)-6-((2-oxo- 1- (piperidin-4-yl)- 1 ,2-dihydropyridin-3 -yl)amino)imidazo[ 1 ,2-b]pyridazine-3-carboxamide(0.0 15 g, 0.028 mmol), 4-methyl-1H-imidazole-2-carboxylic acid (6.97 mg, 0.055 mmol), BOP (0.024 g, 0.055 mmol) and N,N-Di-iso-propylethylamine (0.018 g, 0.138 mmol) in DMF (1.0 mL) was stirred at room temperature overnight. The reaction mixture was concentrated. The residue was dissolved in 2m1 dichloromethane. 0.2 ml TFA was added and the reaction mixture stirred at room temperature overnight. The crude productmixture was chromatographed using Reverse-Phase PREP LC to give N-cyclopropyl-6- ((1 -(1 -(4-methyl- 1H-imidazole-2-carbonyl)piperidin-4-yl)-2-oxo- 1 ,2-dihydropyridin-3- yl)amino)-8-(methylamino)imidazo [1 ,2-b]pyridazine-3 -carboxamide (0.007g, 0.014 mmol, 50% yield) as a white solid.

The synthetic route of 70631-93-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem