Month: May 2021

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. 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, A new synthetic method of this compound is introduced below., Product Details of 29518-68-1

General procedure: To a 50-ml glass round-bottom flask was added sequentially the primary amine 2 (1.0 mmol; aliphatic, aromatic or heteroaromatic; as free naked amine or as HCl, MsOH, TsOH or tartrate salt), FSO2N3 solution (containing 1.0 mmol FSO2N3, approximately 200 mM in DMF/MTBE 1:1, v/v, approximately 5 ml, volume adjusted according to the concentration; prepared according to the above procedure and diluted with equal volume of DMF) and aqueous KHCO3 solution (3.0 M, 1.33 ml, containing 4.0 mmol KHCO3). The reaction mixture was stirred for 5 min at room temperature, while monitoring by LC-MS. After completion, EtOAc (40 ml) was added and the mixture was washed sequentially with brine (60 ml × 6), water (60 ml × 2) and brine (60 ml), dried over Na2SO4, concentrated by rotary evaporation and dried under vacuum to afford the azide product 3. For products containing acidic functional groups, this extraction process was modified with acidified aqueous phase (acidified with aqueous HCl). Detailed procedures and the various modifications, as well as the characterization data for each compound, can be found in Supplementary Information 1.

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; Meng, Genyi; Guo, Taijie; Ma, Tiancheng; Zhang, Jiong; Shen, Yucheng; Sharpless, Karl Barry; Dong, Jiajia; Nature; vol. 574; 7776; (2019); p. 86 – 89;,
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Imidazole | C3H4N2 – PubChem

Related Products of 149520-94-5, A common heterocyclic compound, 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate, molecular formula is C6H9N3O2, 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.

The mixture of 2-amino-lH-imidazole-4-carboxylic acid ethyl ester (220 mg, 1.42 mmol, 1.0 eq), 3-chloro-6-chloromethyl-quinoline (301 mg, 1.42 mmol, 1.0 eq) and K2C03 ( 294 mg, 2.13 mmol, 1.5 eq) in DMF ( 8 mL) was stirred at 50 C overnight. The reaction mixture was diluted with water and extracted with EA. The combined organic layers was dried and concentrated. The resulting residue was purified by chromatography on a silica gel column (DCM/MeOH = 20/1, v/v) to give 2-amino-l-(3-chloro-quinolin-6- ylmethyl)-lH-imidazole-4-carboxylic acid ethyl ester (100 mg, 21%) and 2-amino-3-(3- chloro-quinolin-6-ylmethyl)-3H-imidazole-4-carboxylic acid ethyl ester (120 mg, 26%) as a yellow solid.

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; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, 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. COA of Formula: C4H8ClN3

Intermediate 69; 6-Chloro-iV-( 1 -methyl- lH-imidazol-4-vO- 1 -(tetrahvdro-2H-pyran-2-vO- 1 H-pyrazolo [3 A- dlpyrimidin-4-amineTo a solution of 4,6-dichloro-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4-d]pyrimidine(Intermediate 70, 3.168 g, 11.60 mmol) in ethanol (60 mL), was added TEA (4.04 mL, 29.00 mmol) followed by 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 1.549 g,11.60 mmol). The resulting mixture was heated at 600C for 2 hours. Evaporation of the volatiles under reduced pressure gave a residue, which was purified utilizing ISCO (EtOAc/hexanes0->80%) to give the title product (1.56g).LCMS: 334 [M+Eta]+.

The synthetic route of 1-Methyl-1H-imidazol-4-amine hydrochloride 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

Reference of 29518-68-1,Some common heterocyclic compound, 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, molecular formula is C9H11N3, 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.

Under argon protection, [RuCl2(C6H6)] 28.2 mg (0.0164 mmol) and (S)-SEGPHOS 20 mg (0.0328 mmol) was suspended in 2 ml of argon gas degassed DMF.Stir at 100 C for 1 hour; The solvent was removed under vacuum at 50 C. Obtained a brown solid; Then, add beta-bimaH 5.3 mg (0.0328 mmol) and2.6 ml of argon gas degassed DCM (dichloromethane)-methanol mixed solvent (DCM:methanol = 10:3),Then add Et3N9.9mg (0.0984mmol),Stir at room temperature for 12 hours under argon protection; The solvent was removed in vacuo, 3 mL DCM was added and filtered.The filtrate was concentrated under reduced pressure to about 0.5 ml.Add 3 ml of n-hexane to precipitate, filter, wash twice with 3 mL of diethyl ether, and dry in vacuo.The product was obtained in 23.3 mg (yield 76%).

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

Reference:
Patent; Zhongshanyi Antai Pharmaceutical Technology Co., Ltd.; Ke Lisidian·A·shanduofu; Xu Liang; Pa Telike·boermate; A Shenli·woke; (18 pag.)CN103889995; (2016); B;,
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

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

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

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. 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

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