Month: September 2021

These common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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: C11H12N2O2

Method A 4-Amino-3-benzimidazol-2-yl-6-(4-methylpiperazinyl)hydroquinolin-2-one Ethyl 2-benzimidazol-2-ylacetate (1.1 eq) and 2-amino-5-(4-methylpiperazinyl)benzenecarbonitrile (1.0 eq) were dissolved in 1,2-dichloroethane, and then SnCl4 (11 eq) was added. The mixture was heated at reflux overnight. Upon cooling, the mixture was concentrated in vacuo. NaOH (3 M) was added to the solid, and the mixture heated at 80 C. for 0.5 hours. The solid was filtered and washed sequentially with H2O, CH2Cl2, and acetone. LC/MS indicated that the product was present in the acetone layer and the solid. These fractions were combined and purified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N) to give the desired product. LC/MS m/z 375.4 (MH+), Rt 1.65 minutes.

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

Reference:
Patent; Chiron Coporation; US2003/28018; (2003); A1;; ; Patent; Renhowe, Paul A.; Pecchi, Sabina; Machajewski, Timothy D.; Shafer, Cynthia M.; Taylor, Clarke; McCrea JR., William R.; McBride, Christopher; Jazan, Elisa; US2002/107392; (2002); 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Chloro-1H-benzo[d]imidazole

To a solution of 2-Chloro-1- isopropyl-1H-benzoimidazole (167.5 mg, 1.00 mmol) in DMF (4 mL) was added NaH (60% in mineral oil, 36 mg, 1.2 mmol) at 0 oC. After stirring 30 minutes at r.t., 2-Bromo-propane (244 mg, 1.20 mmol) was added dropwise and the reaction mixture was stirred at 37 oC for 12 hours. Then the reaction was quenched by water (30 mL) and extracted with EtOAc (50 mL x 3). The combined organic layer was washed with brine and dried over Na2SO4. The mixture was filtered and the filtrate solvent was removed under reduced pressure. The residue was purified via silica gel column chromatography (Petroleum ether/EtOAc) to give the title compound (105 mg, 53.2% yield) as a white solid. LC-MS: Calculated exact mass = 194.1; Found [M+H]+ =195.2; 197.2.

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; KLUGE, Arthur F.; (282 pag.)WO2019/140387; (2019); 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

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

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

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

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

Related Products of 96797-15-8, These common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-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 4-IODO-1-TRITYL-LH-IMIDAZOLE (25 g, 57.2 mmoles) in THF (150 ML) at room temperature was added ethylmagnesium bromide (69 ml, 68. 7 mmoles) under dry conditions. After stirring for 90 minutes, zinc chloride (9.4 g, 68.6 mmoles) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (triphenylphosphine) palladium (6.6 g, 5.72 mmoles) and 5-BROMO-2-METHOXYPYRIDINE (8.9 ml, 68. 7 mmoles) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane (500 ml) and washed with a 30% NaOH solution containing an added 20 g of EDTA (3x 200 ML), with NaCl (sat. ) (200 ml), dried over MGS04, filtered, and concentrated. To the crude material was added dichloromethane (200 ml) and trifluoroactetic acid (40 ml, 410 mmoles). After standing for 6 hours, the reaction was concentrated and pumped on overnight. The crude material was purified by flash chromatography using 0-5% MEOH/CH2CL2 with 0.1% triethylamine yielding 5-imidazol-4-yl-2-methoxypyridine (7. 0g, 70%). MH (176)

The synthetic route of 96797-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; WO2004/96823; (2004); A2;,
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

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