Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, 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 89088-69-7, category: imidazoles-derivatives

A mixture of 4-benzenesulfonyl-2,6-dichloro-pyridine (0.40 g, 1.39 mmol), 1-methyl- lH-imidazole-4-amine hydrochloride (0.22 g, 1.67 mmol) and DIPEA (0.7 mL, 4.16 mmol) in anhydrous DMSO (4.6 mL) was flushed with nitrogen and heated at 120 C in a sealed microwave vial (plastic lid) for 2 h. The mixture was then partitioned between EtOAc (20 mL) and saturated aqueous ammonium chloride solution (10 mL) and the phases separated. The aqueous phase was extracted with EtOAc (2 x 10 mL) and the combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over MgS04, filtered and concentrated in vacuo. The crude material was purified by flash silica chromatography (eluting with 1-8% MeOH in DCM) to give the title compound as a yellow solid (0.14g, 82% purity, 24% yield). MS: m/z = 349.0 (M+H)+.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

58442-17-4, name is 1H-Benzimidazole-5-carbaldehyde, 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. SDS of cas: 58442-17-4

General procedure: 4.94g (56.7mmol) of MnO2 were added to a solution of 1.40g (9.45mmol) of 7 in 50mL of MeOH. After 48hat rt, the mixture was filtered over slica and by evaporation 1.24g (90%) of compound 8 was isolated.

The synthetic route of 58442-17-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alvarez, Raquel; Gajate, Consuelo; Puebla, Pilar; Mollinedo, Faustino; Medarde, Manuel; Pelaez, Rafael; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 167 – 183;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26530-93-8, name is 1-Methyl-1H-benzo[d]imidazol-6-amine, 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 26530-93-8, Formula: C8H9N3

Acetic anhydride (1.08 ml, 11.4 mmol) was added to a solution of 1-methyl-1H- benzo[d]imidazol-6-amine (800 mg, 5.44 mmol) in dioxane (20 mL) at 0 °C. The mixture was stirred at room temperature for 16 hours, concentrated in vacuo, and the residue was diluted with water. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried with Na2SO4, filtered, and concentrated in vacuo to provide the title compound; mass ion (ES+) of 190.4 [M+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, 1-Methyl-1H-benzo[d]imidazol-6-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 109012-23-9, 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. 109012-23-9 name is Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, 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.

To a solution of ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (500 mg, 2.20 mmol) in methanol (7.5 mL)-THF (15 mL) was added 2M aqueous sodium hydroxide solution (3.8 mL, 7.53 mmol) at room temperature. The mixture was stirred for 3 hr at 40C, neutralized with 1M hydrochloric acid, extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (200 mg) as a brown solid (yield 46%). 1H NMR (300 MHz, DMSO-d6) delta 3.96 (3H, s), 8.58 (1H, s). * The peak of “COOH group” was not observed.

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 6953-65-7,Some common heterocyclic compound, 6953-65-7, name is (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol, molecular formula is C8H7ClN2O, 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.

N-Methyl-2-methanol-5-chlorobenzimidazole 49 was prepared according to using the procedure by Harisha et al. [28] A solution of 5-chloro-(1H-benzimidazole-2-yl)-methanol 28 (1.50 g, 8.20 mmol), and sodium hydroxide (0.33 g, 8.2 mmol) were stirred in dry acetone (30 mL) for 30 min. Then, iodomethane (1.41 g, 8.20 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl to neutralize the excess potassium carbonate. The solid was washed with cold water (100 mL) and aqueous ethanol. The product was purified by column chromatography (9:1 chloroform/ethanol) to give the desired product 38 as bright orange crystals Yield 9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol, its application will become more common.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
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. 253453-91-7, name is 2-Chloro-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Chloro-1-methyl-1H-imidazole

Step A’: 2-Chloro-3-methyl-3H-imidazole-4-carbaldehyde. To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel is added 2-chloro-1-methyl-1H-imidazole (1 equiv.) and THF (0.5 M). The reaction mixture is cooled to -78 C. and n-BuLi (2.5 M in hexanes, 1.05 equiv.) is added. The resulting mixture is stirred for 1 h and a solution of DMF (1.05 eq) in THF (2.5 M) is then added dropwise. After the addition is complete, the cooling bath is removed and the reaction is allowed to warm to rt. The reaction mixture is quenched with satd. aq. NH4Cl, transferred to a separatory funnel, and extracted with EtOAc. The organic layer is washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents are evaporated under reduced pressure to yield the product. The material is purified by recrystallization or column chromatography

According to the analysis of related databases, 253453-91-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); 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. 865998-46-5, name is Ethyl 5-nitro-1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 865998-46-5

15 g (81 mmol) of 4-nitro-1H-imidazole-2-carboxylic acid ethyl ester is stirred under argon together with 13.13 g (97.2 mmol) of cyclopropyl methyl bromide and 22.4 g (162 mmol) of potassium carbonate in 165 ml of DMF for 1 hour at 80 C. After cooling, the reaction mixture is diluted with water and extracted four times with ethyl acetate. The combined organic phases are washed once with water and three times with saturated sodium chloride solution, dried with magnesium sulfate, and concentrated by evaporation in a vacuum. The crystalline residue is immediately reused for the next reaction. Yield: 17.59 g (70% of theory) LC-MS (Method 1): Rt=2.02 min. MS (EST+): m/z=240 [M+H]+ 1H-NMR (300 MHz, DMSO-d6): delta=8.2 (s, 1H), 4.4 (q, 2H), 4.3 (d, 2H), 1.4 (m, 4H), 0.55 (q, 2H), 0.45 (q, 2H) ppm.

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; AICURIS GMBH & CO. KG; Schwab, Wilfried; Schiffer, Guido; Voegtli, Kurt; Kyas, Andreas; Osswald, Gerd; US2014/315924; (2014); 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. 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8N2O2

[Step 2] Methyl 6-nitro-1H-benzimidazole-4-carboxylate Methyl 1H-benzimidazole-4-carboxylate (315 mg) was dissolved in conc. sulfuric acid (3 mL), and the solution was stirred on ice bath. A small amount of potassium nitrate (199 mg) was added portion-wise, the solution was stirred at room temperature for 4 hours. The reaction mixture was poured into ice, alkalified with 3N aqueous sodium hydroxide solution under stirring on ice bath, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate. The titled compound (334 mg) was obtained as colorless powder after distilling off a solvent under reduced pressure.

According to the analysis of related databases, 37619-25-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; OTSU, Hironori; EP2746265; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16405-79-1, 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. 16405-79-1, name is 2-Cyclopropyl-1H-benzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(R)-((2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)-6-(3-methylmorpholino)-pyrimidin-4-yl)imino)dimethyl-lambda6-sulfanone A reaction vial was charged with Int. D (120 mg, 0.39 mmol), 2-cyclopropyl-1H-benzo[d]imidazole (94 mg, 0.59 mmol), Pd2dba3 (18 mg, 0.02 mmol), XPhos (16 mg, 0.04 mmol), Cs2CO3 (380 mg, 1.17 mmol) and dioxane (6 mL). The vial was purged with N2 for 2 min., sealed and heated to 150 C. for 1 h in a microwave reactor. The reaction mixture was cooled to RT, filtered through CELITE, and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC (Mobile phase: A=10 mM NH4HCO3/H2O, B=MeCN; Gradient: B=40-70%; 15 min; Column: Agela C18, 10 mum, 150 A, 21.2 mm*250 mm) to afford the title compound (83.0 mg, 50% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) delta 8.10 (dd, J=6.8, 2.3 Hz, 1H), 7.53 (dd, J=6.5, 2.2 Hz, 1H), 7.24-7.14 (m, 2H), 5.93 (s, 1H), 4.36 (s, 1H), 3.94 (dd, J=16.4, 8.5 Hz, 2H), 3.72 (d, J=11.4 Hz, 1H), 3.61 (dd, J=11.4, 2.9 Hz, 1H), 3.50-3.44 (m, 1H), 3.42 (s, 6H), 3.17 (td, J=13.0, 3.9 Hz, 1H), 3.09-3.01 (m, 1H), 1.21 (d, J=6.7 Hz, 3H), 1.17-1.11 (m, 2H), 1.09-1.02 (m, 2H); MS (ES+) C18H22N6O2S requires: 426, found: 427 [M+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, 2-Cyclopropyl-1H-benzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Board of Regents, The University of Texas System; DI FRANCESCO, Maria Emilia; JONES, Philip; CARROLL, Christopher Lawrence; CROSS, Jason Bryant; RAMASWAMY, Suyambu Kesava Vijayan; JOHNSON, Michael Garrett; LIVELY, Sarah; LAPOINTE, David; US2019/16713; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4589-66-6, These common heterocyclic compound, 4589-66-6, name is (1,2-Dimethyl-1H-benzo[d]imidazol-5-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.

a) (1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol To a suspension of 1,2-Dimethyl-1H-benzo[d]imidazole-5-carboxylic acid (crude, 2.54 g, approx. 9.35 mmol) in MeOH (15.5 ml)/toluene (78 ml) Trimethylsilyldiazomethane (2 M solution in hexane, 7.0 ml, 14 mmol) was added at 0-10 C. The reaction mixture was stirred at it for 1 hour. The reaction mixture was evaporated under reduced pressure. The residue was taken up in DCM, Remaining insoluble solid was filtered off. The filtrate was evaporated again to dryness to afford crude Methyl 1,2-dimethyl-1H-benzo[d]imidazole-5-carboxylate

The synthetic route of 4589-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; US2012/35168; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem