Month: April 2021

Adding a certain compound to certain chemical reactions, such as: 2849-93-6, name is 1H-Benzimidazole-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 2849-93-6, category: imidazoles-derivatives

A mixture of tert-butyl 3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)azetidine-1-carboxylate (intermediate 55, 450 mg, 1.479 mmol), trifluoroacetic acid (3.29 mL, 44.4 mmol) and dichloromethane (3 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and dried under high vacuum. The crude 3-(azetidin-3-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (250 mg, 0.598 mmol), 1H-benzimidazole-2-carboxylic acid (97 mg, 0.598 mmol), HBTU (227 mg, 0.598 mmol), triethylamine (0.416 mL, 2.99 mmol) and dry dimethylformamide (2 mL) were added to a 50 mL round bottom flask. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with saturated ammonium chloride and dried over magnesium sulfate before concentrating in vacuo to give the crude material as a tan solid. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g, hexane to ethyl acetate gradient) to provide 3-(1-(1H-benzo[d]imidazole-2-carbonyl)azetidin-3-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (16 mg, 0.048 mmol, 8.01% yield) as off-white solid. M+1=335.1 1H NMR (400 MHz, DMSO-d6) delta ppm 4.42 (t, J=9.29 Hz, 1H) 4.66 (dd, J=10.27, 6.16 Hz, 1H) 4.97-5.03 (m, 1H) 5.21-5.36 (m, 2H) 6.92 (dd, J=7.82, 5.28 Hz, 1H) 7.12-7.18 (m, 1H) 7.18-7.25 (m, 2H) 7.44 (d, J=7.82 Hz, 1H) 7.62 (d, J=8.22 Hz, 1H) 7.84 (dd, J=5.28, 1.37 Hz, 1H) 11.13 (br. s., 1H) 13.16 (br. s., 1H)

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.

17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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. Recommanded Product: 17325-26-7

Step B: Sodium hydride (519 mg, 21.6 mmol) was added to a cooled (0 C.) solution of the compound prepared in Step A (4.03 g, 14.4 mmol) and methyl 4-imidazolecarboxylate (2.0 g, 16 mmol) in 100 mL of DMF. The reaction mixture was allowed to warm to rt. After 16 h at rt no desired product was observed, and the reaction mixture was heated to 50 C. for 163 h. Although a significant amount of the starting material (the mesyl intermediate) remained, the reaction mixture was diluted with 150 mL of diethyl ether, washed with water (5×150 mL) and brine (1×150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by MPLC (silica gel, 0-60% EtOAc/hexanes) afforded the desired product and recovered starting material. ESI-MS calculated for C15H23N3O4: 309.36. found 310 (M+H).

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

Synthetic Route of 16681-59-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16681-59-7 name is 2-Bromo-1-methyl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A flask was charged with tert-butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (1.90 g, 5.47 mmol, 1.1 eq), 2-bromo-1-methyl-imidazole (800 mg, 4.97 mmol, 1 eq), (1,1′-bis(diphenylphosphino)ferrocene) palladium(II) dichloride (181 mg, 0.24 mmol, 0.05 eq), sodium carbonate (1.05 g, 9.94 mmol, 2 eq), dioxane (18 mL) and water (3 mL). The mixture was purged with nitrogen for 5 mins and heated to 110 C. for 12 h. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL*3). The organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuum. The crude residue was purified by column chromatography (petroleum ether:ethyl acetate=1:0 to 3:1). Tert-butyl N-[(1S)-1-[4-(1-methylimidazol-2-yl)phenyl]ethyl]carbamate (850 mg, 2.82 mmol, 56% yield) was obtained as a grey solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Application of 89830-98-8, 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 89830-98-8 as follows.

Methyl 4-bromothiophene-2-carboxylate (3.32 g, 15.0 mmol),4-cyclopropyl-1H-imidazole (1.08 g, 10.0 mmol),Potassium carbonate (4.14g, 30.0mmol),Cuprous iodide (572 mg, 3.0 mmol),1,10-phenanthroline (720 mg, 3.63 mmol),It was added to 50 mL of toluene, and heated to 110 C under a nitrogen atmosphere for 48 hours. The system was cooled to 25 C, the solvent was removed by rotary evaporation, and the residue was applied to silica gel column chromatography (PE: EA = 3:1).The target product (120 mg, yield 4.8%) was obtained.

According to the analysis of related databases, 89830-98-8, the application of this compound in the production field has become more and more popular.

Reference of 10040-98-9, A common heterocyclic compound, 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, molecular formula is C10H8N2O, 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 mixture of malonitrile (60.0 mg, 0.9 mmol) and 4-(1H-imidazol-1-yl)benzaldehyde (155.0 mg, 0.9 mmol) in anhydrous ethanol ( 4.0 mL) was charged with N-methylmorpholine (0.1 mL, 0.9 mmol) for 2 minutes. To the mixture was added 1-methyl-3-(pyrazin-2-yl)-1H- pyrazol-5(4H)-one (159.0 mg, 0.9 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature for 48 hrs. The suspension was filtered under vacuum and off white solid was obtained. The solid was gently washed with hexanes (20 mL) and chilled ethanol (10 mL) and further dried under high vacuum to provide compound 23 as an off white solid (340 mg, 95%).1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.98 (s, 1H), 8.50-8.42 (m, 2H), 8.14 (s, 1H), 7.63 (s, 1H), 7.45 (d, J = 8.4 Hz, 2H), 7.28 (d, J = 8.4 Hz, 2H), 7.05 (s, 1H), 5.08 (s, 1H), 3.85 (s, 3H). MS (ESI): Calcd for C21H16N8O: 396, found: 397 (M+H)+.

The synthetic route of 10040-98-9 has been constantly updated, and we look forward to future research findings.

Electric Literature of 3034-50-2, The chemical industry reduces the impact on the environment during synthesis 3034-50-2, name is Imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

Example 10 : Ethyl 4-cyclohexyl-1-[(/?)-2-{3-[5-(1 H-imidazol-4-yl)pentyl]- ureido}-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate10-1-1 1-Trityl- 1 H-imidazole-4-carbaldehyde:To a solution containing 1 g (10.4 mmol) of 1 H-imidazole-4-carbaldehyde and 3.18 g (11.4 mmol) of trityl chloride suspended in 28 ml of acetonitrile are added dropwise 2.5 ml (17.7 mmol) of triethylamine. After stirring for 2 hours at room temperature, 30 ml of water are added and the crude reaction product is filtered. 3.2 g in the form of a beige-coloured powder are obtained and used in the following step without further purification.

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, Imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Some common heterocyclic compound, 3034-38-6, name is 5-Nitro-1H-imidazole, molecular formula is C3H3N3O2, 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: 3034-38-6

A solution of NaOH (1.6 g, 40 mmol) in MeOH (10 mL) was added dropwise to a stirred mixture of 4-nitroimidazole (4.5 g, 40 mmol) and MeOH (40 mL) at rt. After stirring (10min), a trace of insoluble material was filtered off, the clear yellow solution was evaporated under reduced pressure and the residue recrystallised from EtOH to give compound 13 (4.2 g, 79%) as yellow crystals. mp>300 C (lit.17, >300 C). 1H NMR (250.1 MHz, DMSO-d6): d 7.14 (s, 1H, CH), 7.75 (s, 1H, CH). 13C NMR (DMSO-d662.9 MHz): d 131.0 (CH), 145.6 (CH), not observed (CNO2). MS (CI) m/z (%) 112 (M-, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3034-38-6, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 15813-09-9, name is 4,5-Diiodo-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 15813-09-9, Safety of 4,5-Diiodo-1H-imidazole

1 (12.0 g, 37.5 mmol) was dissolved in a reaction system of ethanol (120 mL) and water (20 mL)Na2SO3 (23.6 g, 188.0 mmol),The reaction was refluxed for 72 hours,Ethanol was removed under reduced pressure,Ethyl acetate extraction,Dried over anhydrous magnesium sulfate,Remove the solvent,Methylene chloride was recrystallized to give a white solid,Yield 48.1%.

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, 4,5-Diiodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

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 3314-30-5 as follows. Quality Control of 1H-Benzo[d]imidazole-2-carbaldehyde

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°C, 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 using general procedure 3, (3S)-1-(2-aminoethyl)-N-[(3-fluoropyridin-2- yl)methyl]pyrrolidine-3-carboxamide (438) (150 mg, 0.56 mmol), 1H-1,3-benzodiazole-2-carbaldehyde (82 mg, 0.56 mmol) and DIPEA (196 muIota, 1.13 mmol) in MeCN (10 ml) at room temperature for 16 h, followed by the addition NaBH4 (31 mg, 0.81 mmol) gave the title compound (47 mg, 21percent) as a pale yellow film after purification by basic prep-HPLC. 1H-NMR (MeOD, 500 MHz): d[ppm]= 8.31 – 8.26 (m, 1 H), 7.54 – 7.48 (m, 3H), 7.32 – 7.27 (m, 1 H), 7.23 – 7.17 (m, 2H), 4.55 (d, J= 1.5 Hz, 2H), 4.03 (s, 2H), 3.05-2.97 (m, 1H), 2.83-2.76 (m, 3H), 2.75-2.60 (m, 5H), 2.15-2.06 (m, 1H), 2.06- 1.97 (m, 1H) HPLCMS (Method C): [m/z]: 397.2 [M+H]+

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Electric Literature of 641571-11-1, 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 641571-11-1 as follows.

Example 30[00103] Form A of the free base of 4-methyl-N-[3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-phenyl] -3 -(4-pyridin-3 -yl-pyrimidin-2-ylamino)-benzamide is made according to the following scheme:Eq.)10 EPO [00104] 14.5 g (60.0 mmol) of B6 and 20.8 g (64.8 mmol) of B5 are dissolved in 120 niL tetrahydrofuran absolute at room temperature under inert and water-free conditions. The suspension is cooled to IT 0-5C and 101.0 g (180 mmol) of potassium tert-butoxide solution 20% in tetrahydrofuran were added within 1 hour, maintaining the internal temperature at 0-5C. The reaction mixture is heated gradually to IT 5O0C within 1 hour and then stirred at this temperature for another 1 hour. The reaction mixture (yellow suspension) is quenched at IT 50C by the addition of 50 mL of water. Stirring is stopped, and the two phase system is let to separate. The aqueous (lower) phase is removed. Seeding crystals (0.2 g) of form A are added to the remaining organic phase, and the thin suspension is stirred for 1 hour at 500C during which time crystallization is initiated. Approximately 1.0 mL of acetic acid is added to the organic phase until a pH of ~10 is reached. Solvent (260 mL) is distilled off at 80-1000C (external temperature) under normal pressure, and simultaneously 260 mL ethanol 94% is added keeping the volume constant, i.e., solvent exchange from tetrahydrofuran to ethanol. The suspension is cooled to IT 0-50C within 1 hour, and agitation is continued for another 1 hour. Form A of the free base of 4-methyl-N-[3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-phenyl] -3 -(4-pyridin-3 -yl-pyrimidin-2-ylamino)-benzamide (crystalline solid) is collected by filtration and washed with 150 mL of cold ethanol 94%. The product is then dried at 500C in vacuo.

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.