Tag: M.W=100-200

Synthetic Route of 10394-39-5, These common heterocyclic compound, 10394-39-5, name is 5-Methoxy-1-methyl-1H-benzo[d]imidazole, 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 a solution of 198 5-methoxy-1-methyl-1H-benzo[d]imidazole (500 mg, 3.08 mmol) in 200 CH2Cl2 (6 ml) was added 201 BBr3 (3.1 g, 12.33 mmol) dropwise at 0 C. After addition, the mixture was stirred for 2 h at 0 C. The mixture was then quenched by slow addition to 202 ice water (50 mL). The resulting mixture was extracted with CH2Cl2 (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the 203 title compound (100 mg, 21.9%) as a white solid which was used in next step without further purification. LCMS (m/z): 149.1 (M+1).

The synthetic route of 10394-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Duncan, Kenneth W.; Chesworth, Richard; Boriack-Sjodin, Paula Ann; Munchhof, Michael John; Jin, Lei; (118 pag.)US2019/83482; (2019); 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. 16931-35-4, name is 7-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 16931-35-4

General procedure: To a solution of aryl halide (1.0 equivalence) and boronic acid (1.1 equivalence) in 1,4-Dioxane (1.0 M), was added potassium carbonate (2.0 equivalence, 2.0 M aqueous solution) followed by palladium catalyst [1,1?-bis(diphenylphoshphino)ferrocene]-dichloropalladium (II) 1:1 complex with dichloromethane (0.10 equivalence). The reaction mixture was degassed for 5 minutes by bubbling nitrogen gas directly into the solution using syringe needle. The reaction vessel was closed tightly and stirred at 100 oC for overnight or until the completion of reaction as judged by TLC. The reaction mixture was filtered through a pad of silica/celite to remove the catalyst, poured into water (25 mL) and extracted with ethyl acetate (3 x 25 mL), the organic layer was washed with water (20 mL), dried over Na2SO4 and concentrated and purified by chromatography.

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; Kashyap, Sudhir; Sandler, Joel; Peters, Ulf; Martinez, Eduardo J.; Kapoor, Tarun M.; Bioorganic and Medicinal Chemistry; vol. 22; 7; (2014); p. 2253 – 2260;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89088-69-7,Some common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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.

Intermediate 23; 2-Chloro-Lambda/-(l-methyl-lH-imidazol-4-yl)pyridor2,3-dlpyrimidin-4-amine1 -Methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 167 mg, 1.72 mmol), 2,4- dichloropyrido[2,3-d]pyrimidine (500 mg, 2.50 mmol) were suspended in ethanol (10 mL) and TEA (0.24mL, 1.72 mmol) was added. The reaction mixture was heated at 700C overnight and the title product was obtained after filtration (421mg).1H NMR (300 MHz, DMSO-d6) delta ppm 11.33 (s, 1 H) 9.16 (d, 1 H) 9.01 (s, 1 H) 7.54-7.72(m, 3H) 3.75 (s, 3 H). 103496-1PLCMS: 261 [M+H]4

The synthetic route of 89088-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19485-38-2, name is 1-Methylimidazole-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 19485-38-2, category: imidazoles-derivatives

In a 100 mL round bottom flask was added 1 mmol4,5-dicarboxy-1-methyl-1H-imidazole,1 mmol HOBT, dissolved in 20 mL ethyl acetate and stirred at 0 C for 30 min. Join 1mmol DCC, 0 reaction 2.5h, magnetic stirring.Dropping 1mmol dehydroabiety amine ethyl acetate solution 5mL,Reaction overnight. TLC followed the reaction until the reaction was complete. Then ice bath for half an hour, making DCU precipitation. DCU was removed by filtration and the filtrate was diluted to 200 mL and washed with 5% NaHCO3 (10 mL * 3), 10% citric acid (10 mL * 3) 2-3 times and saturated brine (10 mL * 3). The ethyl acetate layer was dried over anhydrous sodium sulfate. Filtration, the filtrate point plate, two points, the two points separated by the column to give compound L1 and compound L2, respectively, characterized.The L1 yield was 34.7% and the L2 yield was 35.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylimidazole-4,5-dicarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Forestry University; Xu Li; Zhao Fengyi; Lu Wen; Xu Yuanyuan; Wang Luna; Xue Huayu; Cao Fuliang; (9 pag.)CN106220570; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 380177-22-0, The chemical industry reduces the impact on the environment during synthesis 380177-22-0, name is (5-Chloro-1-methyl-1H-benzo[d]imidazol-2-yl)methanol, I believe this compound will play a more active role in future production and life.

A solution of (5-CHLORO-1-METHYL-1H-BENZIMIDAZOL-2-YL) METHANOL (1.5 g, 7.7 mmol) dissolved in CH2CI2 at room temperature was treated with Dess-Martin periodinane (4.9 g, 11.5 mmol). The reaction was stirred for 15 hours before the solvent was removed. The residue was purified by flash column chromatography (0-3% MeOH in CH2CI2) to give the product (1.0 g, 66% YIELD). 1H NMR (300 MHz, CDCI3) 6 : 4.16 (s, 3 H), 7.40-7. 47 (m, 2 H), 7.90-7. 93 (m, 1 H), 10.11 (s, 1 H).

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-Chloro-1-methyl-1H-benzo[d]imidazol-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 149520-94-5, name is Ethyl 2-amino-1H-imidazole-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 149520-94-5, HPLC of Formula: C6H9N3O2

a) Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylate Ethyl 2-amino-1H-imidazole-4-carboxylate (6.45 mmol, 1 g) and triethylamine (10.04 mmol, 1.016 g) were suspended in dry ACN (30 ml) and cooled to 0 C. Acryloyl chloride (9.67 mmol, 0.875 g) dissolved in dry ACN (4 ml) was added dropwise. The resulting mixture was slowly warmed to RT and subsequently heated to 50 C. for 16 h. The solvent was evaporated and the residue purified by flash chromatography. 0.358 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): delta 1.37 (t, 3H), 2.92 (t, 2H), 4.18 (t, 2H), 4.37 (q, 2H), 7.40 (s, 1H), 8.78 (bs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-amino-1H-imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; Toermakaengas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja; US2014/94474; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-52-0, 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. 68282-52-0 name is 2,4-Dimethyl-1H-imidazole-5-carbaldehyde, 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.

94a) 2-(2-(1-benzyl-4-piperidinyl)ethyl)-5,7-dimethyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one To a solution of 2-(1-benzyl-4-piperidinyl)ethanamine (2.2 g), 2,5-dimethylimidazole-4-carbaldehyde (1.2 g) and acetic acid (0.3 ml) in 1,2-dichloroethane (25 ml) was added sodium triacetoxyborohydride (8.1 g) under ice-cooling. The reaction mixture was mixed at room temperature for 2 days, and then the reaction solution was washed with an aqueous potassium carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was dissolved in THF (50 ml). To the reaction solution were added N,N’-carbonyldiimidazole (1.6 g) and DBU (1.6 ml), and mixed at room temperature for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in chloroform. The reaction mixture was then washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate/methanol = 10/1). The product was recrystallized from ethyl acetate-hexane to obtain the title compound as colorless powder (1.3 g, 32%). NMR (CDCl3) delta:1.26-1.35 (2H, m), 1.53-1.59 (2H, m), 1.67-1.74 (2H, m), 1.88-1.97 (1H, m), 1.97 (2H, t, J=10.5), 2.15 (3H, s), 2.56 (3H, s), 2.84-2.90 (2H, m), 3.44-3.49 (2H, m), 3.48 (2H, s), 4.21 (2H, s), 7.20-7.30 (5H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dimethyl-1H-imidazole-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1695961; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 68282-52-0, name is 2,4-Dimethyl-1H-imidazole-5-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H8N2O

88a) tert-butyl 4-(((2,5-dimethyl-1H-imidazol-4-yl)methyl)amino)-1-piperidinecarboxylate N-(tert-butoxycarbonyl-4-piperidinyl)amine (4.8 g), 2,5-dimethylimidazole-4-carbaldehyde (3.0 g) and acetic acid (1.7 ml) were dissolved in 1,2-dichloroethane (50 ml), under ice-cooling, sodium triacetoxyborohydride (7.7 g) was added thereto, and mixed at room temperature for 15 hours. The reaction solution was poured into an aqueous potassium carbonate solution, and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and then the residue was purified with silica gel column to obtain a pale yellow oily title compound (8.0 g, quantitative). NMR (CDCl3) delta:1.27-1.40 (2H, m), 1.45 (9H, s), 1.85-1.90 (2H, m), 2.15 (3H, s), 2.31 (3H, s), 2.66-2.80 (3H, m), 3.71 (2H, s), 4.00-4.18 (2H, m), 6.06 (2H, brs).

The synthetic route of 68282-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1695961; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 29518-68-1, These common heterocyclic compound, 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, 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: Starting amino compound (0.238 mmol) was dissolved in THF (25 mL) and triethylamine (10 drops) was added to the stirred solution. Acyl halide (0.149 mmol) was added dropwise to the stirred solution, which was then heated under reflux for 3h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc and washed with aq. K2CO3 solution followed by brine. The organic layer was then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 1-5 methanol/DCM v/v.

Statistics shows that 2-(1H-Benzo[d]imidazol-2-yl)ethanamine is playing an increasingly important role. we look forward to future research findings about 29518-68-1.

Reference:
Article; Elshihawy, Hosam; Helal, Mohamed A.; Said, Mohamed; Hammad, Mohamed A.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 550 – 558;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 40828-54-4, name is 1H-Benzo[d]imidazole-2-sulfonic acid, molecular formula is C7H6N2O3S, 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. SDS of cas: 40828-54-4

STEP A 2-(3-Hydroxypropylamino)benzimidazole Heat at 145-150 C. for two hours a mixture of 5 g (25 mmol) of 2-benzimidazolesulfonic acid and 5.7 ml (75 mmol) of 3-aminopropanol. Cool to 90 C. and add 15 ml of cold water, with vigorous stirring, until a precipitate is formed. Maintain at a temperature of approximately 4 C. for one night, filter the title compound precipitate, wash with cold water and dry. Yield: 95% Melting point: 139-140 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40828-54-4, its application will become more common.

Reference:
Patent; Adir Et Compagnie; US5623073; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem