Author: Jessica.F

144689-93-0, Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-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 144689-93-0.

20L reactor was added 300.0g (1.25mol) imidazole mono-, 1043.6g (1.87mol) BBTT, 44.8g (1.87mol) of lithium hydroxide and 7kg acetonitrile. The reaction system was increased to 70-75 5h, TLC or HPLC in control, raw reaction was complete. After cooling to 30-45 system To the system was added in portions 280.6g (5.0mol) of potassium hydroxide and 700g of water to form a solution. Plus complete, insulation reaction 4-5h, TLC or HPLC in control, raw reaction was complete. After 300g of water added to the system dropwise acetic acid adjusted to pH 5.5 to 6.5. After stirring for 1h incubation continued cooling to room temperature, filtered, the filter cake washed with a small amount of acetone to obtain 777.4g of intermediate 5 run. HPLC: 95.9%,Yield: 90.4%.

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Bang Pharmaceutical Co., Ltd.; Zhao, Guangrong; Huan, Shuang; Zhao, Huayang; Liu, Liping; Chen, Guoping; Tang, Jingyu; (19 pag.)CN105481842; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 15788-16-6, name is 1H-Benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O2, 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. 15788-16-6.

Preparation 26 Methyl 5-benzimidazolecarboxylate A mixture of 10 g of 5-benzimidazolecarboxylic acid, 150 ml of methanol and 100 ml of a 4N solution of hydrogen chloride in 1,4-dioxane was agitated ultrasonically for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, after which 300 ml of methanol and 3.5 g of lithium borohydride were added to the residue and the mixture was stirred for 1 hour. The solvent was then removed by evaporation under reduced pressure and the residue was mixed with an aqueous solution of sodium chloride, after which it was extracted with ethyl acetate. The solvent was removed by distillation under reduced pressure, to give 5.44 g of the title compound, melting at 136-138 C.

The synthetic route of 1H-Benzo[d]imidazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5886014; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, 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 934-22-5 as follows.

Example 133; N-1H-Benzimidazol-5-yl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 2,2,2-Trichloroethyl 1H-benzimidazol-5-ylcarbamate; To a solution of 1H-benzimidazol-5-amine (1.00 g, 7.51 mmol) and pyridine (0.73 ml, 9.01 mmol) in tetrahydrofuran (25 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.25 ml, 9.01 mmol), and the mixture was stirred at room temperature for 1.5 hour . Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 1.49 g (64.4%) of the desired product as a solid was separated by filtration. 1H-NMR (CDCl3) delta; 5.22 (2H, s), 7.27 – 7.29 (1H, m), 7.90 – 8.01 (2H, m), 8.06 (1H, br s), 8.56 (1H, s), 10.16 (1H, br s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, molecular formula is C8H6N2O2, 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. 2849-93-6

A mixture of 3-nitro-N-(piperidin-4-yl)pyridin-2-amine hydrochloride (intermediate 58, 580 mg, 2.3 mmol), 1H-benzo[d]imidazole-2-carboxylic acid (365 mg, 2.3 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (365 mg, 2.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (516 mg, 2.7 mmol) and N-methylmorpholine (455 mg, 4.6 mmol) in dry dimethylformamide (15 mL) was stirred at room temperature overnight. The mixture was diluted with water (60 mL), and extracted with ethyl acetate (2*50 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated to give the crude compound which was purified by silica chromatography to afford (1H-benzo[d]imidazol-2-yl)(4-((3-nitro-pyridin-2-yl)amino)piperidin-1-yl)methanone (600 mg, 1.64 mmol, 72.8% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2849-93-6, its application will become more common.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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: A dry flask was charged with the nitrogen containing heterocycles (1.5 mmol), aryl halides (1 mmol), potassium carbonate(2 mmol) and CuMeSal (0.01 mmol) then anhydrous DMSO (5 ml) was added. The reaction mixture was stirred at 110C, open to air, for 3h , cooled to room temperature, filtered, and the precipitate was washed with DMSO (2 ml) then stirred with ice water (30 ml) and extracted with ethyl acetate (3 ¡Á 50 ml),dried over sodium sulfate and the solvent was removed under reduced pressure.The residue was purified by chromatography or recrystallization as indicated with each compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole, its application will become more common.

Reference:
Article; Farahat, Abdelbasset A.; Boykin, David W.; Tetrahedron Letters; vol. 55; 19; (2014); p. 3049 – 3051;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1080-79-1, These common heterocyclic compound, 1080-79-1, name is Diethyl 1H-imidazole-4,5-dicarboxylate, 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. N-o-Nitrophenylimidazole 4,5-dicarboxylic acid diethyl ester To a solution of o-fluoronitrobenzene (106 g) and imidazole 4,5-dicarboxylic acid diethyl ester (106 g) in one liter of N,N-dimethyl formamide (DMF) was added anhydrous potassium carbonate (200 g). The reaction mixture was stirred vigorously for at least four hours. After removal of solvent under oil pump vacuum, the residue was treated with water, then extracted with chloroform (300 ml*3). The combined chloroform extracts were washed with water, dried by magnesium sulfate, then concentrated under vacuum to an oil. Upon treatment with ether, the oil was solidified and the product was obtained as a white solid (136 g, 81% yield). Recrystallized from chloroform-hexane, m.p. 93-95 C.

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 1080-79-1.

Reference:
Patent; USV Pharmaceutical Corporation; US4440929; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 15788-16-6, name is 1H-Benzo[d]imidazole-5-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 15788-16-6

8.1. PREPARATION OF 5-BENZIMIDAZOLE-CARBOXYLIC ACID, METHYL ESTER A 500 ml round bottom flask equipped with a heating mantle, reflux condenser, and a DrieriteR filled drying tube was charged with 16.22 g (0.10 mol) of 5-benzimidazolecarboxylic acid (Aldrich), 400 ml of anhydrous methanol and then (Caution)) 20 ml of concentrated sulfuric acid (Fisher). The reaction mixture was heated to reflux for 18 h and then cooled to ambient temperature. Approximately 75% of the solvents were removed under vacuum and then the remaining liquid residue was slowly poured into 500 ml of saturated sodium bicarbonate solution. The resultant two phase system was then extracted with three 250 ml portions of ethyl acetate. The organic layers were combined and washed with three 250 ml portions of 5% sodium bicarbonate solution followed by one 250 ml portion of brine. The ethyl acetate layer was dried over MgSO4, filtered and the solvents were then removed under reduced pressure to give 15.68 g (0,089 mol, 89% yield) of 5-benzimidazolecarboxylic acid, methyl ester, as a tan solid. 1 H NMR (CDCl3) delta7.3-7.9 (m, 3H), 3.70 (s, 3H).

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, 15788-16-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytogen Corporation; US5326856; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17334-08-6, These common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, 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 2-hydroxymethyl-1-methylimidazole (874 mg) was added thionyl chloride (10 ml) at 0C, and the mixture was heated for 30 minutes under nitrogen atmosphere at 90C. The mixture was allowed to be at room temperature. The solvent was distilled off under reduced pressure and the obtained residue was recrystallized from ethyl acetate, to give 2-chloromethyl-1-methylimidazole hydrochloride (1.15 g) as brown crystals. 1H-NMR (200 MHz, DMSO-d6) delta 3.88 (3H, s), 5.19 (2H, s), 7.72 (1H, d, J = 1.8 Hz), 7.78 (1H, d, J = 1.8 Hz). Elemental Analysis C5H8N2Cl2 Calcd. C, 35.95; H, 4.83; N, 16.77; Found. C, 35.74; H, 5.03; N, 16.45.

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 17334-08-6.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1422228; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 2849-93-6 as follows. 2849-93-6

General procedure: A reaction mixture of H2BIC (0.0162 g,0.1mmol), Gd(NO3)3¡¤6H2O (0.0451 g, 0.1 mmol), Na2C2O4 (0.0134 g, 0.1 mmol), CH3CN(5 mL) and EtOH (5 mL) was stirred for 20 min, then transferred and sealed in a 20mLTeflon-lined autoclave. The system was heated in an oven at 393K for 72 h and cooled toroom temperature at 5Kh1. The resulting colorless flaky crystals were collected, washedwith ethanol and dried in air. Yield: ca. 71% (based on Gd). Anal. Calcd forC24H15N6O6Gd (%): C, 44.99; H, 2.36; N, 13.12. Found (%): C, 45.21; H, 2.88; N, 12.92.IR (KBr)/cm1: 3131(br, m), 1659(s), 1616(s), 1528(m), 1498(m), 1460(s), 1394(s),1319(s), 1307(m), 1230(w), 1029(w), 989(w), 850(m), 821(m), 773(w), 741(s), 657(m),592(m).

According to the analysis of related databases, 2849-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Qiao, Chengfang; Xia, Zhengqiang; Wei, Qing; Zhou, Chunsheng; Zhang, Guochun; Chen, Sanping; Gao, Shengli; Journal of Coordination Chemistry; vol. 66; 7; (2013); p. 1202 – 1210;,
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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 46006-36-4

A mixture of l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.14 mmol, HC1 salt), lH-benzo[d]imidazole-4- carboxylic acid (57 mg, 0.35 mmol) and EDCI.HC1 (30 mg, 0.16 mmol) in pyridine (2 mL) was heated at 30 C for 12 h. A yellow suspension was formed. LCMS (Rt = 0.586 min; MS Calcd: 531.2; MS Found: 532.2 [M+H]+). The mixture was concentrated and the residue was poured into water (20 mL) and stirred for 2 minutes. The aqueous layer was extracted with ethyl acetate (20 mL x3). The combined organic layer was washed with water (20 mL x2) and brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by prep-HPLC (0.225% FA as an additive) and lyophilized to give N-(5-((5-methyl- 8-(2-oxopyrrolidin-l-yl)-5H-chromeno[4,3-c]pyridin-3-yl)amino)pyridin-3-yl)-lH- benzo[d]imidazole-4-carboxamide (41.7 mg, yield: 55%) as a yellow solid. (1559) NMR (400 MHz DMSO-rie) d 1.56 (3H, d, J= 6.5 Hz), 2.01-2.10 (2H, m), 2.52-2.54 (2H, m, overlapped with the peak of DMSO), 3.84 (2H, t, J= 7.9 Hz), 5.30 (1H, q , J= 6.7 Hz), 6.79 (1H, s), 7.32 (1H, dd, J= 8.7, 2.1 Hz), 7.40 (1H, d, J= 2.3 Hz), 7.47 (1H, t , J= 7.8 Hz), 7.88-7.92 (2H, m), 8.03 (1H, d, J= 7.5 Hz), 8.62 (1H, d, J= 2.0 Hz), 8.66 (1H, s), 8.72 (1H, s), 8.75 (1H, t, J= 2.0 Hz), 8.81 (1H, d, J= 2.0 Hz), 9.72 (1H, brs), 12.06 (1H, brs).

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; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem