Month: January 2021

Electric Literature 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: A mixture of CoCl2¡¤6H2O (0.1 mmol, 0.0237 g), imidazole-4,5-dicarboxylate (0.1 mmol,0.0156 g), 1,4-bis(1-imidazoly)benzene (0.1 mmol, 0.0210 g), NaOH (0.2 mmol, 0.0800 g), H2O(10 mL) and DMF (2 mL) was stirred for 1 h in air, then transferred to and sealed in a 25 mLTeflon-lined reactor and heated in an oven to 110 C for 72 h. After cooling to room temperature,brown block crystals of 1 were collected by ltration and washed with water and DMFseveral times.

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; Wang, Ke-Hua; Journal of Coordination Chemistry; vol. 70; 24; (2017); p. 3982 – 3995;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1, 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 8 SYNTHESIS OF 4-(3-CHLORO-4-FLUORO-PHENYLAMINO)-5-(5-METHYL-3H-IMIDAZOL4-YLMETHYLENE)-5,7-DIHYDRO-PYRROLO [2,3-D]PYRIMIDIN-6-ONE (FORMULA 8) 4-Chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (1 eq.) was condensed with 5-methyl-3H-imidazole-4-carbaldehyde (1 eq.) at room temperature to give (76.9%) of 4-chloro-5-(5-methyl-3H-imidazol-4-ylmethylene)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one.

The synthetic route of 5-Methyl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liang, Congxin; Sun, Li; Wei, Chung Chen; Tang, Peng Cho; McMahon, Gerald; Hirth, Klaus Peter; Cui, Jingrong; US2002/183319; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3314-30-5, A common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, -(2-aminoethyl)-N’-[(3-fluoropyridin-2- yl)methyl]propanediamide (418) (190 mg , 0.75 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (120 mg, 0.82 mmol) and MgS04 (100 mg) in DCM (10 ml) and MeOH (5 ml) at room temperature for 16 h, followed by addition of NaBH4 (57 mg , 1 .51 mmol) gave the title compound (87 mg, 28percent) as a pale yellow solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.14 (s, 1 H), 8.59 (t, J = 5.5 Hz, 1 H), 8.40 – 8.35 (m, 1 H), 8.06 (t, J = 5.5 Hz, 1 H), 7.69 (m, 1 H), 7.57 – 7.47 (m, 1 H), 7.47 – 7.36 (m, 2H), 7.16 – 7.08 (m, 2H), 4.48 (dd, J = 5.5, 1 .7 Hz, 2H), 3.91 (s, 2H), 3.20 (dt, J = 6.5, 6.5 Hz, 2H), 3.13 (s, 2H),2.63 (t, J = 6.5 Hz, 2H) HPLCMS (Method C): [m/z]: 385.2 [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; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
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. 35203-44-2, name is 1-Propyl-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Propyl-1H-imidazole

General procedure: A solution of N-alkylimidazole (10 mmol, 2 equivalents) and Dibromoalkane (5 mmol, 1 equivalent) was refluxed in toluene (20 mL) for 24?30 h. The reaction mixture was allowed to cool and toluene was decanted leaving a sticky solid behind. The sticky solid was washed three times with dry THF and finally with diethyl ether once. Solvent was removed under vacuum to get a white amorphous hygroscopic powder (88?94 percent yield). NMR spectra were recorded in D2O and/or DMSO-d6.

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; Aher, Sainath Babaji; Bhagat, Pundlik Rambhau; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5587 – 5596;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 54624-57-6, A common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Step 2. 2-(lH-Benzoimidazol-2-yl)-3-cyclohexyl-lH-indole-6-carboxylic acid methyl ester (10.3)A reaction flask was charged with 100 mg (0.26 mmol) 10.2, 64 mg (0.33 mmol, 1.25 eq) 2-bromobenzimidazole and 15 mg (0.013 mmol, 0.05 eq) Pd(PPh3 )4. To this was added 4 mL dioxane and 1 mL NaHCO3 (sat., aq.). The reaction mixture was degassed and purged with Argon (2x), and then gently heated to 90 0C for 4 h. HPLC and LC-MS analysis confirmed complete consumption of 10.2. The reaction mixture was allowed to cool to room temperature and then concentrated. The desired methyl ester was precipitated by addition of cold H2O and collected by centrifuge. 10.3 was dried under vacuum and used without further purification. MS: 374.1 (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; GENELABS TECHNOLOGIES, INC.; WO2008/11521; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1231930-33-8,Some common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, molecular formula is C11H12BrFN2, 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.

The 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo [d] imidazole (9.0 g, 33.2 mmol)Bis-boronic acid pinacol ester(0.65 g, 49.8 mmo1), palladium acetate (840 mg), tricyclohexylphosphine (1.63 g) and potassium acetate (9,78 g, 99.8 mmo 1) were added to 60 mL of DMSO and the nitrogen was allowed to warm to 80 C for 6 h.The organic phase was extracted with EA, and the organic phase was washed with EA. The organic phase was dried with anhydrous sodium sulfate and filtered through the filtrate. The filtrate was concentrated and purified by silica gel column chromatography (PE: EpsilonAlpha = 1: 2) The title compound (6.0 g, yield 56.8%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu, Yongqian; (45 pag.)CN104910137; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]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 13275-42-8, category: imidazoles-derivatives

General procedure: Equimolar quantity of 2-(2-bromophenyl)-1H-benzo[d] imidazole (2) and aniline derivatives in 45 ml of 1,4-dioxan was refluxed for 14 hr with continuous stirring at 80. The completion of reaction was checked by TLC. The reaction mixture was kept overnight in a refrigerator. The solvent was evaporated and a gummy solid mass was obtained. The gummy solid was then washed with cold water and recrystallized from ethanol and water (4:6) to obtain the compounds (3a-3h).

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; Singh, Aruna Chandra; Mittal, Nitin; Pathak, Devender; Indian Journal of Heterocyclic Chemistry; vol. 23; 3; (2014); p. 225 – 232;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2849-93-6, These common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic 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.

0.064 mmol of BENZIMIDAZOLECARBOXYLIC acid 41 was dissolved in DMF together with 0.064 MMOL of the amine 5d, a solution of TBTU (0.096 MMOL) in DMF, HOBT (0.026 MMOL) in DMF and 0.32 MMOL of DIPEA were added successively, and the mixture was stirred at room temperature. After 2.5 hours, 0.2 eq. of acid was added, and the mixture was stirred overnight. After further addition of 0.2 eq. of acid, the reaction mixture was diluted with water after 3 hours, and the resulting precipitate was filtered off with suction, washed with water and digested with diethyl ether. Yield : 76%, pale-beige solid

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GmbH; WO2005/4863; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17325-26-7, These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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.

Preparation 121 1-Trityl- 1H-imidazole-4-carboxylic acid methyl ester Add triethylamine (1.88 mL, 13.48 mmol) to a mixture of methyl-4-imidazolecarboxylate (1.0 g, 7.93 mmol) and triphenylmethyl chloride (2.43 g, 8.72 mmol) in anhydrous acetonitrile (25 mL) over 10 min at room temperature and stir overnight. Quench with water and extract with ethyl acetate (3*). Combine the organic layers, wash with 1N hydrochloride solution, water, saturated aqueous sodium bicarbonate solution and brine sequentially, dry over sodium sulfate, and concentrate to provide the title compound 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol).

Statistics shows that Methyl 1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 17325-26-7.

Reference:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); 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. 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

Example 45: Synthesis of 4-(4-Methyl-[l,4]diazepan-l-yl)-l,7,llb-triaza-benzo[c]fluorene- 6-carboxylic acid ethyl ester (Compound 8A) [0329] To a solution of SMI (176 mg, 1 mmol) and SM2 (204 mg, 1 mmol) in 2- Methoxyethanol (10 mL) was added N-Methylhomopiperazine (342 mg, 3 mmol) and the mixture was stirred at room temperature for 20 min. The reaction mixture was heated to reflux for 16h. The crude product was purification by gel silica column (DCM/MeOH=50: l) to get compound 8A as brown oil (320 mg, 79 yield). LCMS: m/z 404 (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; HADDACH, Mustapha; WO2015/172123; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem