Tag: M.W=100-200

614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, 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. Formula: C8H8N2

General procedure: A sealable reaction tube equipped with a magnetic stirrer barwas charged with 5,6-dimethyl-1H-benzo[d]imidazole (0.50 mmol,73 mg), benzaldehyde (1.0 mmol, 106 mg), di-tert-butyl-peroxide(1.0 mmol, 146 mg), 4 A molecular sieves (50 mg) and ethyl acetate(3.0 mL). The rubber septum was then replaced by a Teflon-coatedscrew cap, then the reaction must be under N2 and the reactionvessel placed in an oil bath at 110 C. After stirring the mixture atthis temperature for 15 h, it was cooled to room temperature anddiluted with ethyl acetate then washed with 0.5 mmol/L NaOHaqueous solution (5.0 mL3), dried over by MgSO4. After the solventwas removed under reduced pressure, the residue was purifiedby column chromatography on silica gel (hexane/EtOAc, 4:1 to6:1) to afford the desired product (5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone (3a, 116 mg, 93% yield).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Lin; Wang, Min; Wang, Lei; Tetrahedron; vol. 70; 35; (2014); p. 5391 – 5397;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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: 10 mL ethanol solution of 2.0 mmol metal salt was added into 10 mL ethanol solution of 2.0 mmol 4,5-imidazole dicarboxylic acid. Having blended the mixture under reflux for 1 h, methanol solution of 1.0 mmol NaOH was put into hot mixture drop by drop. After 5 h under reflux, solvent of the solution was removed, precipitate was filtered. The precipitates were washed with methanol 3 times and dried in 105 C. Molecular structures of complexes obtained from the reaction of 4,5-imidazole dicarboxylic acid ligand with metal salts were summarized in Fig. 2.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4,5-dicarboxylic acid, its application will become more common.

Reference:
Article; Erdem, Ozlem; Yildiz, Emel; Inorganica Chimica Acta; vol. 438; (2015); p. 1 – 4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 25676-75-9, 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 25676-75-9 as follows.

Step 1: A solution of 4-bromo-1-methyl-1H-imidazole (1.0 g, 6.2 mmol), (4-fluoro-3-methylphenyl)boronic acid (1.0 g, 6.5 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.6 g, 0.52 mmol) and aqueous Na2CO3 (2 M, 4 mL, 8.0 mmol) in a mixture of DME/EtOH/H2O (7:3:2, 10 mL) was evacuated and then refilled with nitrogen (three cycles). Resulting reaction mixture was then irradiated in the microwave at 150 C. for 50 min., dried (MgSO4), filtered and concentrated under reduced pressure to give a black residue, which was purified by column chromatography eluting with MeOH/DCM to provide 4-(4-fluoro-3-methylphenyl)-1-methyl-1H-imidazole (0.6 g, 51%). MS m/e: 191 (M+H)+.

According to the analysis of related databases, 25676-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; Bristol-Myers Squibb Company; Kinsella, Todd; Gelman, Marina; Hong, Hui; Darwish, Ihab S.; Singh, Rajinder; Yu, Jiaxin; Borzilleri, Robert M.; Velaparthi, Upender; Liu, Peiying; Darne, Chetan; Rahaman, Hasibur; Warrier, Jayakumar Sankara; (311 pag.)US2016/257690; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, 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. 4857-06-1 name is 2-Chloro-1H-benzo[d]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.

PREPARATION 2 (1-(4-Fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine Combine 2-chloro-1H-benzimidazole (17.75 g, 116 mmol) and 4-fluorobenzyl bromide (26.6 g, 141 mmol) in dimethylformamide (100 mL). Add a solution of sodium hydroxide (50 g) in water (75 mL). (Caution, exothermic). After 30 minutes, pour the reaction mixture into water (1800 mL) and stir to form a solid. After 1 hour, collect the solid by filtration, dissolve the solid in dichloromethane, and extract with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on a short column of silica gel eluding with 5% ethyl acetate/dichloromethane to give a solid. Recrystallize from chloroform/hexane to give, after drying, 1-(4-fluorobenzyl)-2-chloro-1H-benzimidazole.

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

Reference:
Patent; Aventis Pharmaceuticals Inc.; US6211199; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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: 934-32-7

In a 50 mL single-mouth eggplant bottle, 0.55 g (4.1 mmol) of 1H-benzo[d]imidazol-2-amineDissolve in 15 mL of acetone, add 0.70 g (12 mmol) of potassium hydroxide powder and 1.1 g (8.2 mmol) of potassium carbonate, stir at room temperature for 10 min, transfer to ice water bath, add 0.45 mL (4.5 mmol) 2-iodopropane dropwise, and move to Stir in a 65 C oil bath for 3 h.The reaction was detected by TLC, the reaction solution was diluted with EA, the solid was filtered off, the solvent was evaporated, the solvent was evaporated, 10 mL of water was added, and extracted with EA (8 mL*3, combined organic phase, dried over Na2SO4, concentrated, flash silica gel column chromatography (gradient wash) De DCM: MeOH = 100:1 to 30:1) to give 275 mg of pale yellow solid.Yield 38%

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Anyanren Pharmaceutical Technology Co., Ltd.; Xie Dexun; Li Quanwei; Xue Weicai; Liu Hui; (27 pag.)CN108912095; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 106429-59-8, The chemical industry reduces the impact on the environment during synthesis 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, I believe this compound will play a more active role in future production and life.

To the solution of the crude product from Step 6 in MeOH (2 mL) was added NaOAc (14 mg), and 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde (21 mg). The resulting mixture was stirred at RT for 15 min, at which point NaCNBH3 (15 mg) was added to the solution. The resulting mixture was heated at 50 oC overnight to give a clear solution, which was purified directly by preparative RP-HPLC method E to give 5- fluoro-N-isopropyl-N-methyl-2-(1-(1-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5- yl)methyl)piperidin-3-yl)-2-thioxo-1,2-dihydro-3H-imidazo[4,5-c]pyridin-3- yl)benzamide as a TFA salt (1.20 mg); LCMS method B: Rt = 0.54 min; (M+H)+ = 574.6; 1H NMR (MeOH-d4): delta 9.01 (br, 1 H), 8.51 (s, 1 H), 8.21 (s, 1 H), 7.74 (s, 1 H), 7.38- 7.04 (m, 5 H), 4.65 (m, 1 H), 4.48 (m, 1 H), 4.31 (m, 2 H), 3.83 (m, 4 H), 2.87 (m, 2 H), 2.52 (m, 1 H), 2.15 (m, 3 H), 1.99 (m, 1 H), 1.32-0.82 (m, 6 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-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 33543-78-1

Ethyl 1H-imidazole-2-carboxylate (4 g, 28.5 mmol), p-chlorobenzylchloride (4.38 mL, 34.3 mmol), and sodium carbonate (3.63 g, 34.3 mmol), was dissolved in DMF (8 mL).The solution was stirred at rt for 24 h, at which time water was added and material was extracted with EtOAc.The organic phase was collected, dried over magnesium sulfate, and decanted.Purification accomplished via silica gel flash chromatography (150 g silica, 10percent EtOAc/Hexanes to 80percent EtOAc/Hexanes.) The title compound was obtained as a clear, yellow-tinted oil. (Yield: 7.28 g, 27.5 mmol, 96percent) 1H NMR (400 MHz, CDCl3) 7.25, 7.15, 7.10-7.00, 5.55, 4.34, 1.36

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; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; US2012/252807; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 35445-32-0, 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 35445-32-0 as follows.

ethyl [2-BROM-1,] [4-DIMETHYL-1] H-imidazole-5-carboxylate To a solution of intermediate 93 (1.69 [G,] 0.01 mol) in CH3CN (60 mL) was added [NBS (2.15 G, 1.2 EQ. ) AND THE REACTION WAS STIRRED AT RT FOR 1 NIGHT. AFTER EVAPORATION] of the solvant, the residue was dissolved in DCM and washed with water. The organic layer was dried over [NA2SO4] and evaporated off. After purification by flash chromatography using DCM/MeOH 90/10 as eluent, the title compound was obtained as yellow crystals (0.645 g, 2.6 [MMOL)] in 26percent yield ;’H NMR [(CDC13,] 300 MHz) [S] 4.55 (q, 2H), 4.09 (s, 3H), 2.69 (s, 3H), 1.61 (t, 3H)

According to the analysis of related databases, 35445-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/6922; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. SDS of cas: 1849-01-0

A mixture of (±)-trans-N-(6-bromo-8-chloro-3-isoquinolyl)-2-cyano-cyclopropanecarboxamide (200 mg, 0.57 mmol), 1-methyl-2-benzimidazolinone (120 mg, 0.81 mmol), Pd3(dba)2 (100 mg, 0.11 mmol), Xantphos (130 mg, 0.22 mmol) and K3PO4 (360 mg, 1.7 mmol) in 1,4-dioxane (15 mL) was heated at 90 C. for 3 h under Ar. The mixture was concentrated and purified by silica-gel column chromatography (EA:PE=1:3 to 1:2) to give (±)-trans-N-[8-chloro-6-(3-methyl-2-oxo-benzimidazol-1-yl)-3-isoquinolyl]-2-cyano-cyclopropanecarboxamide (120 mg, 50% yield) as a yellow solid. LCMS (ESI) [M+H]+=418.1

The synthetic route of 1-Methyl-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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.

Example 135 (S,Z)-N-(1-(2-chloro-6-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)pyrrolidin-3-yl)-1-methyl-1H-imidazole-2-carboxamideTo a 50 mL vial charged with a magnetic stir bar was added (S,Z)-5-(2-(3-aminopyrrolidin-1-yl)-3-chlorobenzylidene)thiazolidine-2,4-dione (75 mg, 0.23 mmol) (Example 86), 1-methyl-1H-imidazole-2-carboxylic acid (87 mg, 0.69 mmol), HATU (220 mg, 0.58 mmol) and dichloromethane (5 mL). Hunig’s base (0.202 mL, 1.16 mmol) was then added and the mixture was stirred at rt for 4 h. The reaction was then diluted with dichloromethane and washed with water. The mixture was separated with a phase separator tube and the organic phase was evaporated to dryness. The residue was purified by reverse phase chromatography to afford the title compound as a yellow solid (21 mg, 21%). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.89 (s, 1H) 7.51 (dd, 1H) 7.41 (dd, 1H) 7.18-7.27 (m, 2H) 7.01 (s, 1H) 4.67-4.77 (m, 1H) 4.00 (s, 3H) 3.63-3.75 (m, 2H) 3.47-3.54 (m, 1H) 3.36-3.47 (m, 1H) 2.39-2.51 (m, 1H) 2.14 (dd, 1H); m/z 432.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2011/218182; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem