Tag: M.W=100-200

Some common heterocyclic compound, 1179361-84-2, name is Ethyl 1-amino-1H-imidazole-5-carboxylate, molecular formula is C6H9N3O2, 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. Application In Synthesis of Ethyl 1-amino-1H-imidazole-5-carboxylate

Preparation of intermediate II-29; A mixture of intermediate II-30 and NH4CI in 7N NHa/MeOH solution was heated at 90C (sand bath) in a closed vessel for 72h. The reaction was heated at 110C for 24 h. Fresh 7N was added (20 mL) and the reaction was heated at 120C for 5 h. Solvents were evaporated to dryness. The residue was partitioned between EtOAc/water. The organic layer was washed once with water, dried and evaporated to give only 11 mg of residue. The aqueous layer was evaporated to dryness to give 400 mg of a white solid, as a mixture of desired product, intermediate 11-29 and NH4CI salts (yield > 100%) that was used as such in next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1179361-84-2, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco, Javier; WO2011/89400; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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. COA of Formula: C7H7N5

EXAMPLE 36; 3-Cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid {1- [6- (5- amino-1,3, 4-oxadiazol-2-yl)-1-methyl-1 H-benzimidazol-2-yl] cyclobutyl} amide; C- (Di-imidazol-1-yl)-methyleneamine (25 mg, 0.16 mmol) was added in a single portion to a solution of compound 35-3 (Example 35) (80 mg, 0.14 mmol) in THF (4 mL). The resulting solution was heated to 70 C for 16 h, after which time a white precipitate was observed. The reaction was then concentrated under reduced pressure, dissolved in 4 mL DMSO and directly purified on a reversed phase Cis, semi-preparative HPLC column (using a solvent gradient from 5% H20 in MeCN to 100% MeCN) to isolate compound 36-1 (compound 1129, Table 1) as a yellow amorphous solid in >95% homogeneity (19 mg, 23% yield). ‘H NMR (400 MHz, DMSO): 5 1.54-1. 67 (m, 2H), 1.79-1. 94 (m, 6H), 1.95-2. 06 (m, 1H), 2.11-2. 23 (m, 1H), 2.74-2. 84 (m, 2H), 3.19-3. 05 (m, 3H), 3.69 (s, 3H), 3.91 (s, 3H), 7.49 (dd, J = 1.8 & 5.7 Hz, 1 H), 7.59-7. 71 (m, 3H), 7.86-7. 92 (m, 2H) 7. 96-8. 01 (m, 1H), 8.06-8. 10 (m, 1H), 8. 10 (s, 1H), 8.78 (d, J = 4.3 Hz, 1H), 9.51 (s, 1H).

The synthetic route of Di(1H-imidazol-1-yl)methanimine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2005/80388; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16265-04-6, name is 2-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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. Quality Control of 2-Chloro-1H-imidazole

B’-1 (2.05g, 20.0 mmol), B’-2 (3.38 g, 20.0mmol), Pd2(dba)3 (0.18g, 0.2mmol), PtBu3 (0.04g, 0.4mmol) and KOtBu (1.44g , 15.0 mmol) were dissolved in 40 ml of toluene, and the mixture was stirred at 80 C for 4 hours. The reaction mixture was cooled to room temperature, and extracted three times with 50 mL of water and 30 mL of diethyl ether. The combined organic layer was dried over MgSO4 and the solvent was evaporated. The resulting residue was purified by silica column method to obtain Intermediate B-1 (3.86 g, yield 82%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16265-04-6, its application will become more common.

Reference:
Patent; Choi Don-su; Choi Jin-sol; (70 pag.)KR2019/35043; (2019); 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. 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Formula: C9H11N3O

A mixture of 1.00 g (4.71 mmol) of ethyl (2-cyano-3-ethoxyprop-2-enoyl)carbamate (for preparation see: Senda, Shigeo, Hirota, Kosaku, Notani, Jiyoji; Chemical & Pharmaceutical Bulletin (1972), 20(7), 1380-8) and 835 mg (4.71 mmol) of 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-one in 5 ml of acetonitrile and 10 ml of DMF was stirred at reflux temperature overnight. After cooling to RT, the mixture was diluted with 150 ml of diethyl ether and the precipitate was filtered off. The filter residue was stirred with 10 ml of methanol, and the solid was filtered off, washed with a little methanol and ether and dried under high vacuum. This gave 703 mg (45% of theory) of the title compound. LC-MS (Method 1): Rt=0.53 min; m/z=298 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=3.30 (br. s, 3H), 3.36 (br. s, 3H), 7.17 (dd, 1H), 7.23-7.28 (m, 1H), 7.34 (d, 1H), 8.77 (s, 1H).

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; Bayer Pharma Aktiengesellschaft; Furstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Zubov, Dmitry; Schamberger, Jens; (69 pag.)US2016/244415; (2016); A1;,
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Imidazole | C3H4N2 – PubChem

Related Products of 570-22-9, These common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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: 10 mL ethanol solution of 2.0 mmol metal salt was added into 10 mL ethanol solution of 2.0 mmol 4,5-imidazole dicarboxylic acid. Having blended the mixture under reflux for 1 h, methanol solution of 1.0 mmol NaOH was put into hot mixture drop by drop. After 5 h under reflux, solvent of the solution was removed, precipitate was filtered. The precipitates were washed with methanol 3 times and dried in 105 C. Molecular structures of complexes obtained from the reaction of 4,5-imidazole dicarboxylic acid ligand with metal salts were summarized in Fig. 2.1.

Statistics shows that 1H-Imidazole-4,5-dicarboxylic acid is playing an increasingly important role. we look forward to future research findings about 570-22-9.

Reference:
Article; Erdem, Ozlem; Yildiz, Emel; Inorganica Chimica Acta; vol. 438; (2015); p. 1 – 4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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. HPLC of Formula: C7H7N3

Compound 473: 1 -(1 H-benzo[d]imidazol-6-yl)-5-(2,6-difluorophenyl)-3-hydroxy-4- methyl-1 H-pyrrol-2(5H)-one; 1H-Benzoimidazol-5-ylamine (1 mmol) was dissolved in 5ml_ of dry EtOH and 2,6-difluoro – benzaldehyd (1 mmol) were added. The solution was stirred overnight and after that 2-oxal- propionsaure diethylester (1 mmol) was added and the solution was stirred for 2Oh at 500C. After that the solvent was evaporated and remaining oil was subjected to a flash chromatography device and purified by means of a CHC^/MeOH gradient. The purified carboxylic acid ethyl ester derivative was suspended in 1OmL of a 10% aqueous solution of HCI and kept for 3h at reflux. The resulting precipitate was filtered off and dried.Yield: 0.098g (28 %);1H-NMR 400 MHz, CD3OD11.81 (s, 3H, CH3), 6.17(s, 1 H, CH-N), 6.72 – 6.83 (m, 1 H, aro), 6.93 – 7.08 (m, 1 H, aro) 7.21 -7.37 (m, 1 H, aro), 7.74(m, 2H, benzimid), 8.07 (s, 1 H, benzimid), 9.28 (s, 1 H, benzimid) MS m/z 342.0 (M+H)+, HPLC (254 nm): purity 99 % molecular weight (g/mol): 341.31 Ki: hQC (nM): 29.2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 934-22-5, its application will become more common.

Reference:
Patent; PROBIODRUG AG; WO2008/55945; (2008); 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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 51605-32-4

To a mixture of ethyl 4-methyl-1H-imidazole-5-carboxylate (7.30 g, 45.9 mmol) in THF (60 mL) is added MeOH (2.23 mL, 55.1 mmol) and triphenylphosphine (14.8 g, 55.1 mmol). The reaction is cooled to 0° C. under N2 and diethyl azodicarboxylate (9.0 mL, 17.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred overnight. The volatiles are evaporated in vacuo. Ether (50 mL) is added. The mixture is stirred at room temperature for 30 minutes, filtered, the filter cake is washed with ether (50 mL). The filtrate and ether washings are combined and are sequentially washed with water (30 mL) and brine (30 mL). The organic phase is dried over Na2SO4, evaporated in vacuo to provide the crude product. The crude product is subjected to silica gel flash column eluting with 30percent EtOAc in hexanes to EtOAc to give the title compound (5.13 g, 59.8percent) as a yellow oil. LC/MS (m/z): 169 (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; Eli Lilly and Company; Hu, Zhi Long; Liu, Lian Zhu; Ma, Tianwei; Zhang, Haizhen; Zhou, Jingye; (25 pag.)US2018/194755; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 45676-04-8,Some common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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: 1-substituted 3-allylimidazolium chloride (2 mmol) was dissolved in 25 mL of dichloromethane and transferred into a Schlenk vessel. Excess Silver(I) oxide (1.5 mmol) was added, and the mixture was stirred for24 h at room temperature under argon atmosphere [19]. Then the unreactedAg2O was filtered through a plug of Celite. The resulting solution was filtered through celite, solvent was evaporated in vaccuo,washed with diethylether (2 mL×2) and dried in vacuo.[RuBr2(PPh3)3] (1 g, 1 mmol) was taken up in 5 mL of dichloromethane and added to a solution of Ag complex in 10 mL of CH2Cl2. The mixture was stirred overnight at room temperature. After filtration in air, the solvent was removed in vacuum to give the product. The final compound is stable in air. Single crystals of the compound 3a were achievedby slow evaporation of a concentrated solution in a mixture of dichloromethane and acetone.

The synthetic route of 45676-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Murugan, Kaliyappan; Vijayapritha, Subbarayan; Viswanathamurthi, Periasamy; Bertani, Roberta; Malecki, Jan Grzegorz; Inorganica Chimica Acta; vol. 486; (2019); p. 55 – 62;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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 137049-00-4, HPLC of Formula: C4H5ClN2O2S

(1-Methylimidazol-4-yl)sulfonyl chloride (23 mg, 0.13 mmol) was added dropwise to a stirred solution of 3-[4-(2-ethyl-5-methyl-2H-pyrazol-3-yl)piperidin-1-yl]-1-phenylpropylamine (see Example 8) (48 mg, 0.15 mmol) and Et3N (20 muL, 0.14 mmol) in CH2Cl2 (2 mL) at RT under N2. The mixture was stirred for 18 h, then was diluted with CH2Cl2 (20 mL) and washed with NaHCO3 solution (20 mL). Then the organic layer was separated and the aqueous phase was re-extracted with CH2Cl2 (20 mL) and the combined organic extracts dried (MgSO4), and concentrated under reduced pressure. The residue was taken up in Et2O (5 mL) and purified by trituration. The title compound (55 mg, 56%) was isolated as a colourless solid. 1H NMR (d6-DMSO, 400 MHz) delta8.28 (1H, d, J=7.8 Hz), 7.68 (1H, s), 7.54 (1H, s), 7.26-7.14 (5H, m), 5.81 (1H, s), 4.35-4.25 (1H, m), 3.93 (2H, q, J=7.2 Hz), 3.60 (3H, s), 2.75-2.50 (3H, m), 2.09 (3H, s), 2.08-2.00 (2H, m), 1.95-1.40 (8H, m), 1.27 (3H, t, J=7.2 Hz). MS (ES+) C24H34N6O2S requires: 470, found: 471 (1:1, M+H+).

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

Reference:
Patent; Chambers, Mark Stuart; Jones, Philip; Szekeres, Helen Jane; US2004/2504; (2004); 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. 83741-35-9, name is 4-Bromo-1H-benzoimidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-1H-benzoimidazole

Preparation 46B: 4-Bromo-l- 2,4-difluorophenyl)-lH-benzo[d]imidazole[00149] A vial charged with molecular sieves, 4A (200 mg, 2.030 mmol) was flame- dried, then allowed to cool to room temperature. To this vial were added 4-bromo-lH- benzo[d]imidazole (0.400 g, 2.030 mmol), copper (II) acetate (0.553 g, 3.05 mmol), and 2,4-difluorophenylboronic acid (0.962 g, 6.09 mmol) followed by (¾(¾ (Volume: 10.15 ml) and triethylamine (0.736 ml, 5.28 mmol). The heterogeneous green reaction was stirred at room temperature. After 19 h, the reaction was filtered through a disposable filter funnel and the filter cake rinsed with (¾(¾. The filtrate was concentrated to afford a green residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (12 g column, 30 mL/min, 0-45% EtOAc in hexanes over 15 min, tr = 10.5 min) gave Preparation 46B (7.5 mg, 0.024 mmol, 1.195% yield) as a yellow solid. MS (ESI) : m/z = 31 1.0 [M+H]+. HPLC Peak tr = 1.73 minutes. HPLC conditions: Column:Luna CI 8 4.6x30mm 3u A: 10:90 H20:ACNNH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow.

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 83741-35-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HUANG, Audris; WO2012/44537; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem