Tag: M.W=100-200

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. Formula: C7H7N3

The compound was synthesized as hydrochloride salt by the following procedure.Phenyl chloroformate (0.98 mL, 7.8 mmol) was dissolved in CH2Cl2, cooled down to 0 C. and 5-aminobenzimidazole (0.865 g, 6.5 mmol) was added slowly. The mixture was kept at 0 C. for 30 min and then the mixture was allowed to adapt ambient temperature. The mixture was stirred at ambient temperature for 2 h. The resulting solid was withdrawn by suction, dried and taken up in a small amount of DMF. To the solution, 1-amino-3,3-dimethylbutan-2-one (0.986, 6.5 mmol) and TEA (2.73 mL, 19.5 mmol) were added. The mixture was kept at 40 C. for 2 h. The solvent was removed and purified by means of preparative HPLC. The remains were re-dissolved in MeOH and a small amount of HCl was added (1-2%). The solution was subjected to hydrogenation (PdC, 10% on charcoal, 4 bar, 60 C.) for 4 h. The catalyst was removed by filtration through a pad of CELITE and the residue was washed with water. The organic layer was dried, filtrated and the solvent was removed to result in the final product. Yield: 0.087 g (6.3%); MS m/z 259.4 (M+H)+; 1H NMR (DMSO, 400 MHz): delta 0.72 (s, 9H); 3.23-3.27 (m, H); 3.46-3.50 (m, H); 4.37-4.41 (m, H); 6.84 (bs, H); 7.56 (dd, H, 3J=9.1 Hz, 4J=1.7 Hz); 7.70 (d, H, J=9.1 Hz); 7.81 (d, H, 4J=1.7 Hz); 9.27 (s, H), HPLC (lambda=214 nm, [B]: rt 6.83 min (99%).

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; US2011/92501; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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: 6-Aminobenzimidazole

To a solution (6 ML) of 1-[5-amino-2-(benzhydryloxy)phenyl]-2-methylpropan-1-one (190 mg, 0.550 mmol) in acetonitrile were added diisopropylethyl amine (0.110 ML, 0.660 mmol) and N,N’-disuccinimidyl carbonate (169 mg, 0.660 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour.. To the reaction solution were added diisopropylethyl amine (0.110 ML, 0.660 mmol) and 1H-benzoimidazol-5-amine (87.8 mg, 0.6605 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 12 hours.. The reaction solution was poured into water and was extracted with ethyl acetate.. The extracted solution was washed with water, and was dried with anhydrous magnesium sulfate.. The solvent was distilled off under reduced pressure, and the residue was purified by silicagel column chromatography (ethyl acetate:methanol = 10:1).. The fractions containing the titled compound were collected, which was washed with water, was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain the titled compound as a solid. 102 mg (36.7%) 1H-NMR (CDCl3) delta; 0.96 (6H, d, J = 7.0 Hz), 3.39 to 3.46 (1H, m), 6.07 (1H, s), 6.63 to 6.77 (2H, m), 7.18 to 7.46 (15H, m), 8.16 (2H, bs)

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1437344; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1977-72-6, 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. 1977-72-6, name is 5-Fluoro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-fluoro-1H-benzoimidazole (0.50 g, 0.00367 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60percent dispersion in oil, 0.44 g, 0.011 mol). After addition, the resulting mixture was stirred for 2 h. (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide (1.29 g, 0.00367 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at room temperature under argon. The reaction was quenched by water, extracted with ethyl acetate. The organic layer was dried with MgSO4, filtered, and concentrated under vacuum. The product was purified by a silicon gel column using methylene chloride and methanol (19:1) as eluent to afford 0.17 g of the desired compound as white solid. 1H NMR (400 MHz, DMSO-d6)^10.37 (s, 1H, NH), 8.31 (d, J = 17.2 Hz, 1H, ArH), 8.16-8.05 (m, 3H, ArH), 7.62-7.56 (m, 1H, ArH), 7.44 (dd, J = 9.60 Hz, J = 2.4 Hz, 1H, ArH), 7.04 (dd, J = 9.60 Hz, J = 2.4 Hz, 1H, ArH), 6.49 (s, 1H, OH), 4.65 (d, J = 5.6 Hz, 1H, CH), 4.62 (d, J = 5.6 Hz, 1H, CH), 1.47 (s, 3H, CH3). Mass (ESI, Negative): 404.8[M-H]-; (ESI, Positive): 429.0[M+Na]+.

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

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; PAGADALA, Jayaprakash; DUKE, Charles B.; COSS, Christopher C.; DALTON, James T.; (296 pag.)WO2016/172358; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10394-38-4, 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. 10394-38-4, name is 1-Methylbenzoimidazol-5-amine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

12.5 N-(1-methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide; 0.18 g (1.23 mmol) of 5-amino-1-methylbenzimidazole and 10 ml of dry toluene are placed, while flushing with nitrogen, in a 100 ml three-necked flask cooled to 0 C. and equipped with a magnetic stirrer. To this solution is then added slowly 0.95 ml (1.90 mmol) of a 2M solution of trimethylaluminum in toluene. The reaction mixture obtained is maintained under a nitrogen atmosphere and stirred, while allowing the temperature to rise gradually to 70 C. A solution of 0.3 g (0.95 mmol) of product obtained in step 12.4 in 10 ml of dry toluene is then added dropwise over 5 minutes using an addition funnel. The reaction mixture is then refluxed for 5 hours and stirred at room temperature overnight. 20 ml of cold water are then added to the solution cooled to 0 C., followed by addition of 10 ml of 1N hydrochloric acid. After stirring for 1 hour, the precipitate is recovered by filtration, rinsed with water and dried under reduced pressure. 0.22 g (0.53 mmol) of the expected product is obtained in the form of a white solid.Melting point: 266-268 C.1H NMR (DMSO D6), delta (ppm): 9.5 (s, 1H); 8.5 (s, 1H); 7.9 (s, 2H); 7.5 (m, 3H); 7.3-6.8 (m, 5H); 5.9 (s, 2H); 3.95 (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, 1-Methylbenzoimidazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2008/125459; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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. Computed Properties of C4H3F3N2

To a solution of a tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (0.5 g, 1.8 mmol, CASRN: 15 8407-04-6) in dry DMF (4 mL) was added 4-(trifluoromethyl)-1H-imidazole (293 mg,2.16 mmol) and Cs2CO3 (1.17 g, 3.59 mmol). The reaction mixture was then stirred at 80 C for14 h. Insolubles were removed by filtration, and the filtrate was concentrated in vacuo. Thecrude residue was suspended in DCM and filtered through a pad of Celite to give a yellow oil,which was purified by flash chromatography with a 5i02 column, using an eluent mixture of nheptane and EtOAc (10% to 90%). This yielded the first fraction (301 mg) of the desired product as a colorless oil, and a second fraction (261 mg) of a mixture of the desired product with impurities. The second fraction was submitted for SFC purification, and the purified product was combined with the first fraction to yield 430 mg of the desired product as a colorless oil. MS(ESI): m/z = 334.2 [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 33468-69-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ANSELM, Lilli; BENZ, Joerg; GRETHER, Uwe; GROEBKE ZBINDEN, Katrin; HEER, Dominik; HORNSPERGER, Benoit; KROLL, Carsten; KUHN, Bernd; O`HARA, Fionn; RICHTER, Hans; (268 pag.)WO2020/35425; (2020); 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1,2-dimethyl-1H-imidazole

General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

According to the analysis of related databases, 24134-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Step 2: Intermediate 34-c To a solution of (l-methyl-lH-imidazol-5-yl) methanol (3.1 g, 27.6 mmol) and intermediate 34-b (4.01 g, 23.04 mmol) in toluene (25.0 ml) and DMPU (25.0 ml) was added sodium 2-methylpropan-2-olate (4.43 g, 46.1 mmol). The reaction was stirred overnight at 80 °C and then cooled to room temperature. A saturated aqueous solution of ammonium chloride and ethyl acetate were added, the organic layer was separated, washed twice with a saturated aqueous solution of ammonium chloride and brine, dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 34-c as beige oil.

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; PHARMASCIENCE, INC.; LAURENT, Alain; ROSE, Yannick; JAQUITH, James B.; WO2013/177668; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-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 71759-89-2, Recommanded Product: 5-Iodo-1H-imidazole

Step 1:To a 000 mixture of 4-iodoimidazole AlOa (5.0 g, 25.8 mmol) (Synthonix) in anhydrous THF (100 mL) is added NaH (60% in oil, 1 .24 g, 30.9 mmol). The resulting mixture is stirred for 10 mm before the addition of 4-methoxybenzyl chloride (4.37 mL, 32.2 mmol) (Aldrich). This mixture is allowed to warm to RT and is stirred overnight. An aqueous solution of saturated NH4CI (50 mL) is added and this mixture is stirred for 10 mm. The mixture is extracted with EtOAc (3x) and the layers are separated. The organic layer is washed with water and brine, dried with Mg504 and concentrated to provide crude material that is purified by Combif lash (20:80 to 80:20, EtOAc/hexanes) to provide AlOb.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; BILODEAU, Francois; POIRIER, Maude; PARISIEN, Mathieu; KUHN, Cyrille; THIBEAULT, Carl; TRINH, Thao; WO2014/70978; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Recommanded Product: (1-Methyl-1H-imidazol-2-yl)methanol

Synthesis of 2-(Chloromethyl)-1-methyl-1H-imidazole Hydrochloride (BB7) To a solution of (BB6) (35.5 g, 316.96 mmol) in DCM (1500 mL) was added SOCl2 (330 mL, 4436 mmol) at 0 C. The reaction was warmed to ambient temperature and stirred for 5 h. The reaction mixture was concentrated, the residue was washed with DCM (2*500 mL), followed by Et2O (2*200 mL) to obtain (BB7) (50 g, 95%) as an off-white solid. Rf: 0.4 (EtOAc). 1H NMR (400 MHz, DMSO-d6): delta 7.76 (1H, app d), 7.70 (1H, app d), 5.17 (2H, s), 3.87 (3H, s); ink 131 (MH)+.

The synthetic route of (1-Methyl-1H-imidazol-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF MANCHESTER; ST GEORGE’S HOSPITAL MEDICAL SCHOOL; US2012/322722; (2012); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 17325-26-7

1H-Imidazole-4-carboxlic acid methyl ester (293.8mg, 2.33mmol), 4-bromo-6- cyclohexyl-pyrane-2-one (300mg, 1. 17mmol) and potassium carbonate (483. 8mg, 3. 50MMOL) were introduced into a 50ML flask, and the flask was then filled with nitrogen gas. After acetonitrile (LOML) was added thereto, the reaction solution was refluxed for 2 hours and then cooled down to room temperature. The precipitate was filtered off, and the filtrate was distilled under reduced pressure. The residue was purified by column chromatography on silica gel using MC: MEOH (20: 1) as eluent. The fractions containing the product were combined and evaporated to give a white solid (290mg, 82.2%). ‘H-NMR (CDCI3) ; 8 =7.99 (2H, m), 6.19 (2H, m), 3.98 (3H, s), 2.52 (1H, m), 1.99 (5H, M), 1.40 (5H, m).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C & C RESEARCH LABORATORIES; WO2004/50624; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem