Category: imidazoles-derivatives

32673-41-9, A common compound: 32673-41-9, name is 4-Imidazolemethanol hydrochloride, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 29 5-chloro-N-((1-(3-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (40) A mixture of 2,5-diiodofluorobenzene II-4 (2.50 g, 7.18 mmol), 4-hydroxymethylimidazole hydrochloride (0.967 g, 7.18 mmol), 8-hydroxyquinoline (0.104 g, 0.717 mmol) and K2CO3 (2.00 g, 14.5 mmol) in DMSO (12 mL) was degassed with Ar before being charged with CuI (0.136 g, 0.716 mmol). The mixture in a sealed tube was heated at 130 C. overnight. After being cooled to room temperature, H2O and EtOAc were added. It was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with MeOH in CH2Cl2 (0-5% MeOH) to give (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol (0.39 g).

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, 4-Imidazolemethanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2007/259924; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 761426-65-7, name is 2-Cyclopropyl-5-iodo-1H-imidazole, molecular formula is C21H29N3O6, 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. 761426-65-7

Example 8 (E-8, Co. No. 25) Pd(PPh3)4 (23.2 mg, 20.1 mmol) was added to a stirred suspension of I-20b (150 mg, – 0.40 mmol) and 2-cyclopropyl-5-iodo-lH-imidazole (112.8 mg, 0.48 mmol) in a sat. sol. of NaHC03 (2 mL) and 1,4-dioxane (1 mL). The mixture was stirred at 120 C for 10 min under microwave irradiation. The mixture was concentrated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH/ DCM 0/100 to 6/94). The desired fractions were collected and evaporated in vacuo. The product was purified by RP HPLC (Stationary phase: C18 XBridge 30 x 100 mm 5 muiotaeta; mobile phase: gradient from 60% 0.1 %> NH4C03H/NH4OH pH 9 solution in water, 40% CH3CN to 43% 0.1% NH4C03H/NH4OH pH 9 solution in water, 57% CH3CN) , to yield Co. No. 25 (90 mg, 51%) as a light yellow fluffy solid. 1H NMR (400 MHz, CDC13) delta ppm 0.91 – 1.02 (m, 4 H) 1.72 (d, J=6.7 Hz, 3 H) 1.90 – 2.00 (m, 1 H) 3.98 (dd, J=12.5, 7.4 Hz, 1 H) 4.24 (dd, J=12.7, 4.2 Hz, 1 H) 4.68 – 4.79 (m, 1 H) 7.28 (s, 1 H) 7.42 (dd, J=8.3, 1.4 Hz, 1 H) 7.60 (d, J=2.1 Hz, 1 H) 7.82 (d, J=8.6 Hz, 1 H) 7.88 (s, 1 H) 11.88 (br s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 761426-65-7, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN GOOL, Michiel, Luc, Maria; ALCAZAR-VACA, Manuel, Jesus; ALONSO-DE DIEGO, Sergio-Alvar; DE LUCAS OLIVARES, Ana, Isabel; (105 pag.)WO2016/87487; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, A common compound: 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

STEP 7: N-(CIS-3-(7,7-DIMETHYL-6-OXO-6,7-DIHYDRO-5H-PYRROLO[2,3-B]PYRAZIN-5-YL)CYCLOBUTYL)-1H-BENZO[D]IMIDAZOLE-2-CARBOXAMIDE To a round bottomed flask was added 5-(cis-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.1518 g, 0.497 mmol), 1H-benzimidazole-2-carboxylic acid (0.097 g, 0.597 mmol, ChemBridge Corporation), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.246 g, 0.647 mmol, GenScript) and triethylamine (0.277 ml, 1.989 mmol, Sigma-Aldrich Chemical Company, Inc.) in DCM (1.658 ml) to stir at room temperature for 5 h. Solvent was evaporated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (50 g), eluting with a gradient of 10% to 100% EtOAc in hexane. LCMS showed product was not isolated at ?95%. The crude product was taken up in DCM and loaded onto an AccuBond SCX cartridge. The cartridge was rinsed with DCM followed by MeOH to remove impurities. The column was then rinsed with 2.0 ammonia in MeOH. The fractions were evaporated in vacuo. The residue was taken up in MeOH at which time a precipitate was noted to form. The round bottomed flask was placed in the freezer overnight. The solid was filtered from the filtrate and washed with cold MeOH to give the title compound (17.1 mg, 0.045 mmol, 9.13% yield). LCMS showed product peak at 1.757 min (m+1=377.0). 1H NMR (400 MHz, DMSO-d) delta ppm 1.35 (s, 6H) 2.71-2.85 (m, 2H) 2.95-3.11 (m, 2H) 4.35 (sxt, J=7.94 Hz, 1H) 4.59 (quin, J=8.46 Hz, 1H) 7.31 (br. s., 2H) 7.55 (d, J=6.26 Hz, 1H) 7.77 (d, J=6.65 Hz, 1H) 8.20 (d, J=3.13 Hz, 1H) 8.27 (d, J=3.13 Hz, 1H) 9.28 (d, J=7.83 Hz, 1H) 13.27 (s, 1H)

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, 1H-Benzimidazole-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 60-56-0 name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. 60-56-0

3-methoxy salicylaldehyde 5 (1 mmol), malononitrile 6 (2.2 mmol), 2-mercaptoimidazole 7 (1.2 mmol), compound4 (20 mol%) and ethanol (5 mL) were sequentially added to a 50 mL round bottom flask, and fully reacted to completion at 80 C (TLC tracking supervision) Measurement). After cooling to room temperature, suction filtration, the product was washed with a small amount of water, dissolved in N,N-dimethylformamide, filtered, and evaporated. The distilled water was precipitated as a solid, suction filtered, and recrystallized (DMSO) to give compound 8j in a yield of 80%. The structural formula of compound 8j is:The formula is: C18H15N6OSChinese name: 2,4-diamino-9-methyl-5-(1-methyl-1H-imidazol-2-ylthio)-5H-chromene[2,3-b]pyridine-3-carbonitrileThe English name is: 2,4-diamino-9-methyl-5-(1-methyl-1H-imidazol-2-ylthio)-5H-Chromeno[2,3-b]pyridine-3-carbonitrile

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-imidazole-2(3H)-thione, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Normal University; Wu Hui; Yuan Rui; Ren Xuanxuan; Fang Yue; Chen Wen; Zhou Shengliang; Zhang Peng; Wan Yu; (15 pag.)CN108610348; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 2034-22-2 as follows. 2034-22-2

2,4,5-tribromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole To a solution of 2,4,5-tribromoimidazole (3.05 g, 10 mmol) in anhydrous DMF (50 mL) was added powdered K2CO3 (19 g, 137 mmol), and the resulting suspension was stirred vigorously and treated dropwise with SEMCl (2.3 g, 13.8 mmol). The suspension was then stirred vigorously overnight. The solid was filtered off and washed with fresh DMF (20 mL). The combined filtrates were then evaporated under reduced pressure. Methylene chloride (30 mL) was then added and the solution washed with 0.1 N Na2CO3 (3*50 mL), dried (Na2SO4), filtered and evaporated to give a residue, which was passed through a silica gel pad (CH2Cl2) and evaporated to give 3.6 g (83%) of the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) delta 0.01 (s, 9H), 0.93 (t, 2H, J=8.0 Hz), 3.60 (t, 2H, J=8.0 Hz), 5.32 (s, 3H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hudyma, Thomas W.; Zheng, Xiaofan; He, Feng; Ding, Min; Bergstrom, Carl P.; Hewawasam, Piyasena; Martin, Scott W.; Gentles, Robert G.; US2006/46983; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-32-7, Name is 1H-Benzo[d]imidazol-2-amine, 934-32-7, 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.

General procedure: A mixture of aldehyde (1 mmol), 2-aminobenzimidazole (1 mmol), malononitrile (1.1 mmol), RHA-[pmim]HSO4 (10 mg, 0.8 mol %) was heated in an oil bath at 100 C under solvent-free conditions for the appropriate time. After completion of the reaction (monitored by TLC), EtOH was added and the catalyst was separated by filtration. Then water was added, and the precipitated product was separated by filtration in high purity. The spectral data of the new compound are as follows:

Statistics shows that 1H-Benzo[d]imidazol-2-amine is playing an increasingly important role. we look forward to future research findings about 934-32-7.

Reference:
Article; Shirini, Farhad; Seddighi, Mohadeseh; Goli-Jolodar, Omid; Journal of the Iranian Chemical Society; vol. 13; 11; (2016); p. 2013 – 2018;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, 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 24134-09-6. 24134-09-6

Intermediate 11: bis(1,2-dimethyl-1H-imidazol-5-yl)methanone A solution of -RuLi (2.66 M in hexane, 19.5 mL, 51.9 mmol) in THF (100 mL) was stirred under argon at-70 C while a solution of 5-bromo-l ,2-dimethyI-lH-imidazole (9.13 g, 52.2 mmol) in TFIF [60 mL; containing 3A molecular sieves (18 g)] was added dropwise over 8 minutes via cannula. After stirring for another 4 minutes at ~-70 C, neat ethyl metboxy(methyl)carbamate (2.96 mL, 22.7 mmol) was added dropwise over 3 minutes. This mixture was stirred at-70 C for an additional 5 minutes, and the cold bath was then removed and the slurry was allowed to warm to room temperature with stirring for 1.5 hours. The reaction was then quenched with 5 aqueous NH4C1 (15 mL), dried (Na2S04), filtered, and concentrated under high vacuum at 80 C, The resulting orange gummy residue was triturated with hot heptane (-40 mL) and the decanted supernatant was allowed to crystallize to provide impure title compound. This was recrystallized from toluene (-30 niL) to provide, after washing the off-white crystalline filter cake with toluene (2 x ~3 mL), the title compound as an off-white crystalline solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5-Bromo-1,2-dimethyl-1H-imidazole.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10111-08-7, 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 10111-08-7 as follows.

General procedure: A typical procedure involves, in a round-bottom flask equipped with a refluxcondenser, in which a mixture of 4-hydroxycoumarin (2 mmol), arylaldehyde(1 mmol), PIL catalyst (10 mol%) and 5 mL of ethanol was stirred at 80 C.The reaction was monitored by TLC. After completion of the reaction, a solidproduct is obtained which is filtered and recrystallized with ethanol(Scheme 2).

According to the analysis of related databases, Imidazole-2-carboxaldehyde, the application of this compound in the production field has become more and more popular.

Reference:
Article; Patil, Sandip K.; Awale, Deepak V.; Vadiyar, Madagonda M.; Patil, Suryakant A.; Bhise, Sagar C.; Kolekar, Sanjay S.; Research on Chemical Intermediates; vol. 43; 10; (2017); p. 5365 – 5376;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-80-3, name is 5-Methoxy-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. 4887-80-3

General procedure: An excess of 5-substituted benzoimidazoles 4a-d (1.5 equiv.) were dissolved in 8 mL of anhydrous acetonitrile and 1.7 equiv. NaH 95% were added portionwise under stirring in a Schlenk tube at room temperature, applying mechanical vacuum until complete evolution of hydrogen gas. After 15 minutes, 1 g (7.14 mmol) of the 4-hydroxy-2-cyclopentenone acetate (¡À)-1 was dissolved in the minimum amount of anhydrous acetonitrile and added to the solution under stirring. The reactions are left under stirring at room temperature overnight. The reactions were quenched with ice mixed with NaCl/NH4Cl 1:3 and the water phase extracted with DCM. The organic phases were dried over Na2SO4 and, upon evaporation of the solvent, the residues were submitted to chromatographic separation to isolate the purified products 5/6a-d

Statistics shows that 4887-80-3 is playing an increasingly important role. we look forward to future research findings about 5-Methoxy-1H-benzo[d]imidazole.

Reference:
Article; Hameed, Karzan Khaleel; Dezaye, Ahmed Anwar; Hussain, Faiq Hamasaid; Basile, Teresa; Memeo, Misal Giuseppe; Quadrelli, Paolo; Arkivoc; vol. 2018; 7; (2018); p. 201 – 213;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem