Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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 570-22-9, name: 1H-Imidazole-4,5-dicarboxylic acid

Thionyl chloride (94 ml; 1.29 mol) was added to a suspension of 1H-imidazole4;5- dicarboxylic acid (25 g; 157 mmol) in toluene (334 ml) and N;N-dimethylformamide (12.1 ml) and the mixture was stirred for 24 h at 80C. The mixture was concentrated under reduced pressure; 100 ml toluene were added and the mixture was concentrated under reduced pressure to give 35.5 g of the title compound as crude material; which was usedat the same day without further purification for subsequent steps.

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, 1H-Imidazole-4,5-dicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERSTAFF, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (136 pag.)WO2017/55313; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, name is 1-Methyl-1H-imidazole-4-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. Computed Properties of C5H6N2O2

Step 6. Synthesis of A/-((1 f?*,3S*)-3-((2-(5-cyano-7-fluoro-1 -tosyl-1 /-/-indol-3-yl)-5- fluoro rimidin-4-yl)amino)cyclohexyl)-1 -methyl-1 /- -imidazole-4-carboxamide. HBTU (522 mg, 1 .38 mmol) was added to a solution of 1 -methyl-1 -/-imidazole-4- carboxylic acid (50.7 mg, 0.40 mmol) in THF (2.5 ml.) at room temperature for 5 minutes under inert atmosphere. Then, a solution of 3-(4-(((1 S*,3 ?*)-3-amino- cyclohexyl)amino)-5-fluoropyrimidin-2-yl)-7-fluoro-1 -tosyl-1 – -indole-5-carbonitrile (200 mg, 0.38 mmol) and A ,A/-diisopropylethylamine (0.24 mL, 1 .38 mmol) in DMSO (0.5 mL) was added and the stirring continued at room temperature for 12 hours. The reaction mixture was diluted with water and extracted with DCM. The organic layers were concentrated under reduced pressure to give a crude that was purified by column chromatography eluting with heptane-EtOAc to yield N- ((1 f?*,3S*)-3-((2-(5-cyano-7-fluoro-1 -tosyl-1 H-indol-3-yl)-5-fluoropyrimidin-4- yl)amino)cyclohexyl)-1 -methyl-1 H-imidazole-4-carboxamide (150 mg, 0.23 mmol). LC-MS ES+ m/z = 631 .2; Rt: 1 .09 min, method E.

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; JONCKERS, Tim, Hugo, Maria; RABOISSON, Pierre, Jean-Marie, Bernard; GUILLEMONT, Jerome, Emile, Georges; MC GOWAN, David, Craig; EMBRECHTS, Werner, Constant, Johan; COOYMANS, Ludwig, Paul; MICHAUT, Antoine, Benjamin; (162 pag.)WO2016/20526; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 615-15-6, 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 615-15-6 as follows.

General procedure: To a stirred solution of 10.0 mmol of compound 1a-1i in 10 mL of conc. H2SO4 we added dropwise 10 mL (0.11 mmol) of 33% aqueous hydrogen peroxide at 100-105C. The mixture was stirred for 0.5 h at 120C, let to cool down, and poured in water. The pH of the solution was adjusted to ~2 with sodium carbonate, and the precipitate of 2-alkylimidazole-4,5-dicarboxylic acid 2a-2i was filtered off and recrystallized from water.

According to the analysis of related databases, 615-15-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brusina; Gubina, Yu. A.; Nikolaev; Ramsh; Piotrovskii; Russian Journal of General Chemistry; vol. 88; 5; (2018); p. 874 – 878; Zh. Obshch. Khim.; vol. 88; 5; (2018); p. 729 – 733,5;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5805-57-2, A common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, molecular formula is C8H9N3, 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: NH4SCN (0.092 g, 1.2 mmol) was dissolved in water (5 ml) and slowly added to the methanolic solution of CuCl2¡¤2H2O (0.1 g; 0.59 mmol) and suitable N-donor ligand, and stirred at room temperature for 12 h. Green crystalline precipitates were filtered off and dried in air. The crystals suitable for X-ray structure determination were obtained by slow recrystallization from methanol.

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; Machura; ?witlicka; Mrozi?ski; Kali?ska; Kruszynski; Polyhedron; vol. 52; (2013); p. 1276 – 1286;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, 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 23814-14-4, Safety of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid

To a stirred solution of 2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carboxylic acid (70 mg), l-(piperazin-l-yl)ethanone84 (50.4 mg) and N,N-diisopropylethylamine (206 mu) in DMF (1 ml) was added HATU (224 mg). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated in vacuo and the residue was purified by preparative reverse-phase HPLC (Gemini NX CI 8, 12 nm, 5mu, 100 x 30 mm, flow rate 40 ml/min, eluant: CH3CN/H2O containing formic acid) followed by lyophilisation to afford 5-(4-acetylpiperazine- l-carbonyl)-lH-benzo[d]imidazol-2(3H)-one (50 mg, 44%) as white solid. MS (ISP): 289.1 ([M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

4-iodo-1H-imidazole (20 g, 103 mmoles) was dissolved in DMF (100 mL) then triethylamine (15.1 mL, 108 mmoles) and triphenylmethyl chloride (27.8 g, 100 mmoles). The reaction mixture was stirred at room temperature for 48 h, then poured into ice water (500 mL), and then evaporated to dryness, and filtered, and dried to give white crystals of 4-iodo-1-triphenylmethyl-1H-imidazole (40 g, 91.7 mmol, 88.9%).

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; Shenzhen Weixin Biological Technology Co., Ltd.; Yu Jindi; Lu Xianping; Li Zhibin; Xin Lijun; Zhu Jiangfei; Fu Chao; (67 pag.)CN108203438; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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 20485-43-2, Formula: C5H6N2O2

A solution of the dipyrrole (50 mg, 0.138 mmol) resulting after coupling of the pyrrolicacid 10, as described in the previous experiment, in MeOH:DMF (4.5 mL : 0.7 mL) was hydrogenated for 1 h over 10% palladium on charcoal (30 mg). The catalyst was removed by filtration through celite and the filtrate concentrated. The residue was dissolved in DMF (1.0 mL), cooled to 0 C and added to a solution of acid 12 (13.4 mg,0.106 mmol), DECP (0.04 mL, 0.212 mmol), Et3N (0.13 mL, 0.903 mmol) and DMAP(catalytic) in THF (3.0 mL) at -10 C. The mixture was stirred for 15 h at -10 C. Thesolvents were removed under reduced pressure and the resulting residue purified by flash chromatography (aluminum oxide, 10% MeOH) to give 1b as a yellow-brownsolid (30.7 mg, 66%).

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:
Article; Jimenez-Balsa, Adrian; Dodero, Veronica I.; Mascarenas, Jose L.; Tetrahedron; vol. 69; 36; (2013); p. 7847 – 7853;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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. Recommanded Product: 7189-69-7

Zn(NO3)26H2O (75 mg, 0.25 mmol), sdi (10 mg, 0.05 mmol) andmalonic acid (52 mg, 0.05 mmol) were mixed in 5 mL of methanol.The pH of the solution was adjusted to 5.0 by the addition of HNO3solution. The mixture was stirred for 30 min at room temperatureand filtered into a glass tube. Colorless crystals of 2 were obtainedin 5 days and collected by filtration, washed with water, and thendried in air. 89% yield (based on sdi). Anal. calcd (%): C, 23.17; H,2.57; N, 22.53. Found (%): C, 23.02; H, 2.64; N, 22.39. IR (KBr, cm1):3447 (m), 3126 (m), 2426 (w), 1637 (m), 1552 (m), 1456 (m), 1384(s), 1206 (m), 1165 (m), 1061 (m), 932 (m), 839 (m), 735 (m), 642(m), 619 (m), 575 (m).

The synthetic route of 1,1′-Sulfonyldiimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Kang; Hu, Hanbin; Sun, Jing; Zhang, Yiheng; Han, Jishu; Wang, Lei; Journal of Molecular Structure; vol. 1134; (2017); p. 174 – 179;,
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

Electric Literature of 16681-59-7,Some common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

Example 40 N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-1 -(1 -methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (E40) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); To a stirred mixture of N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4- imidazolidinecarboxamide (91 mg, 0.3 mmol) (prepared as described in Example 28) and 2-bromo-1 -methyl-1 H-imidazole (48.3 mg, 0.3 mmol) in 1 ,4-dioxane (6 ml) was added potassium phosphate (318 mg, 1.5 mmol), copper (I) iodide (57.1 mg, 0.3 mmol) and trans-N,N-dimethylcyclohexane-1 ,2-diamine (0.047 ml, 0.3 mmol) and the mixture was heated at reflux under argon for 3 hours. The mixture was cooled to room temperature and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organic extracts were separated, washed with water and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-(1- methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (22 mg, 19%). LC/MS [M+H]+ = 384, retention time = 1.69 minutes.

The synthetic route of 16681-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem