Category: imidazoles-derivatives

Related Products of 3012-80-4, 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 3012-80-4 as follows.

To a mixture of thiazolidinedione (6a, 0.5mmol), 1-methyl-1H-benzo[d]imidazole-2-carbaldehydes (10a, 0.55mmol) in ethanol (4mL) was added catalytic amount of piperidine. The reaction mixture was refluxed until complete conversion as observed by TLC. After cooling, the precipitates were filtered, washed and recrystalized with ethanol, to obtain pure (Z)-5-((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)thiazolidine-2,4-dione derivative 11a as yellow solids. All the other compounds 11b?t were obtained in a similar reaction procedure of 11a in moderate to high yields. 5.1.1 (Z)-5-((1-Methyl-1H-benzo[d]imidazol-2-yl)methylene)-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)thiazolidine-2,4-dione (11a) Yellow solid, Yield 82percent; mp: 264?266°C; FT-IR: (cm?1): 2985, 2964, 1740, 1679, 1659, 1385, 1220, 750; 1H NMR (500MHz, DMSO-d6): delta 7.99 (s, 1H), 7.78 (d, J=8.1Hz, 1H), 7.69 (d, J=8.1Hz, 1H), 7.39 (t, J=7.9Hz, 1H), 7.32 (t, J=7.5Hz, 1H), 4.50 (s, 2H), 4.02 (s, 3H), 3.55 (t, J=6.6Hz, 2H), 3.31 (t, J=7.3Hz, 2H), 1.97?1.89 (m, 2H), 1.84?1.77 (m, 2H); 13C NMR (125MHz, DMSO-d6): delta 169.6, 164.8, 162.6, 147.3, 142.6, 135.8, 128.1, 124.2, 123.1, 119.6, 116.7, 111.0, 45.7, 45.0, 42.7, 29.8, 25.8, 23.6; HRMS (ESI): m/z calcd for [M+H]+ C18H19N4O3S 371.1178; found 371.1171.

According to the analysis of related databases, 3012-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sharma, Pankaj; Srinivasa Reddy; Thummuri, Dinesh; Senwar, Kishna Ram; Praveen Kumar, Niggula; Naidu; Bhargava, Suresh K.; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 608 – 621;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 124750-92-1, 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 124750-92-1 as follows.

460 grams of free acid was dissolved in 5 liters of acetic acid, glacial. The solution was filtered through a glass frit. The filtrate was added to 6 liters of 1.1 N HCl in acetic acid, glacial over 1 hour. Crystallization began just prior to the end of filtrate addition, and the resulting material was aged for 1 hour. An ice and water bath was added to cool the batch, and the batch was aged 1 hour. 12.5 liters of isopropyl acetate was added over 1 hour, and the resulting material was aged at 3-4C for 1 hour.Resulting material was filtered and washed with 1 liter isopropyl acetate displacement wash, 2 x 1 liter isopropyl acetate slurry wash, and 2.5 liter isopropyl acetate displacement wash. Resulting material was air dried 45 minutes, then dried by pulling nitrogen through filter cake overnight followed by drying at 350C in a vacuum oven until constant weight. The resulting hydrochloric acid salt was 2-butyl~4-chloro- l-[(2′-(l-H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxylic acid hydrochloride Form I. The solid was then analyzed by X-ray Powder Diffraction. The diffractogram for 2-butyl-4-chloro-l-[(2′-(l- H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxylic acid hydrochloride Form I is characterized by principal d-spacings of 12.96, 4.75, 3.97, 3.79, 3.77, 3.71, and 3.44A, more specifically 12.96, 8.32, 8.13, 7.06, 5.18, 4.75, 4.64, 4.45, 4.41, 4.33, 4.19, 3.97, 3.86, 3.79, 3.77, 3.71, 3.59, 3.44, 3.15, and 2.92A.

According to the analysis of related databases, 124750-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/115834; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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. Application In Synthesis of 1-Methyl-1H-imidazole-4-carboxylic acid

To a solution of (+/-) -cis-N1- (2-chloro-6- (furan-2-yl) pyrimidin-4-yl) cyclohexane -1, 3-diamine (150 mg, 0.51 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) were added N, N-diisopropylethylamine (0.26 mL, 1.54 mmol) and 1-methyl-1H-imidazole-4-carboxylic acid (129 mg, 1.03 mmol) . The mixture was stirred at rt for 10 minitues, and then HATU (389 mg, 1.03 mmol) was added. The resulting mixture was stirred at rt for 3 h. The reaction mixture was diluted with water (20 mL) , and the resulting mixture was extracted with EtOAc (20 mL× 3) . The combined organic layers were washed with saturated brine (50 mL) , dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (150 mg, 73percent) .[0587]MS (ESI, pos. ion) m/z: 401.2 [M+H]+.

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (0 pag.)WO2018/157830; (2018); A1;,
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 1003-21-0 as follows. Product Details of 1003-21-0

intermediate 15: step b(1-methyl-1H-imidazol-5-yl)(pyrimidin-2-yl)methanone5-Bromo-l -methyl- IH-imidazole (6.66 g, 41.4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N? atmosphere. The contents were cooled to 0 C in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0CC and a solution of iV”niethoxy~A,;-methylpyriniidine-2~carboxa.mide (3,09 g, 15.9 mmol, Intermediate 15: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C, then slowly warmed to room temperature, then heated to 40 C in an oil bath and heated with stirring at that temperature for approximately 36 hours. The contents were then cooled to 0 C, quenched with a saturated aqueous NH4C1 solution, diluted with ethyl acetate and transferred to a separatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgS04, filtered, then distilled under reduced pressure to afford an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM / (10% of a 2 M N3 MeOH in DCM)) to provide the title compound.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; 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.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

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-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

73746-45-9, name is 5-Iodo-2-methyl-1H-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. Application In Synthesis of 5-Iodo-2-methyl-1H-imidazole

4-IODO-2-METHYL-LH-IMIDAZOLE (200 mg, 1.0 mmol), 4-fluorophenylboronic acid (215 mg, 1.6 mmol), copper (II) acetate (210 mg, 1.2 mmol) and ET3N (0.16 ml, 1.2 mmol) were sus- pended in 10 ml THF and oxygen was bubbled through the reaction mixture for 40 min. The reaction mixture was stirred for 48 hours at RT and then filtrated over DICALIT. The filtrate was concentrated and then purified by flash chromatography to yield 1- (4-FLUORO- PHENYL)-4-IODO-2-METHYL-LH-IMIDAZOLE (120 mg, 0.40 mmol, 41 %).

The synthetic route of 73746-45-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/80998; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1,Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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 275A 2-chloro-1-methyl-1H-benzo[d]imidazole To a solution of 2-chloro-1H-benzo[d]imidazole (2.0 g, 13.1 mmol) in DMF (10 mL) was added NaH (0.63 g, 15.7 mmol) at 0 C. under N2. After stirring for 30 min at 0 C., iodomethane (5.58 g, 39.3 mmol) was added and the mixture was stirred at room temperature for additional 1 hour. The reaction mixture was quenched with water (100 mL). The aqueous layer was extracted with EtOAc (3*20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the title compound (1.9 mg, 8.9 mmol, 67.9% yield) as a white solid. MS: MS (M+H)+; 1H NMR (400 MHz, CDCl3): delta 7.71-7.68 (m, 1H), 7.31-7.27 (m, 3H), 3.79 (s, 3H).

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2302-25-2, A common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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.

[00622] To a solution of 197-2c (1.0 g, 6.8 mmol, 1.0 eq) in DMF (10.0 mL) was added K2C03 (1.4 g, 10.2 mmol, 1.5 eq) and 197-2b (1.2 g, 7.4 mmol, 0.8 mL, 1.1 eq). The mixture was stirred at 80 C for 2 h. TLC indicated 20% of 197-1 was remained, and one major new spot with lower polarity was detected. The reaction mixture was diluted with H20 (20.0 mL), extracted with EtOAc (10.0 mL * 3). The combined organic layers were washed with brine (30.0 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02) to give 197-2a (500.0 mg, 2.1 mmol, 31% yield). 1HNMR (400 MHz, CDC13) 7.38 (s, 1H), 6.94 (s, 1H), 4.69-4.61 (m, 2H), 4.30-4.20 (m, 3H), 1.35-1.26 (m, 3H).

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; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
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 33543-78-1 as follows. category: imidazoles-derivatives

4-Benzylcarbamoyl-2-(ethoxycarbonylimidazolyl)-1-indanone can be prepared in the following way: a mixture of 0.5 g of 4-benzylcarbamoyl-2-bromo-1-indanone, 0.37 g of 2-ethoxycarbonylimidazole and 10 ml of toluene is heated at reflux for 12 hours. The reaction mixture is concentrated on a rotary evaporator. Dichloromethane is added to the evaporation residue, filtration is carried out and the filtrate is washed with distilled water, dried over sodium sulphate and evaporated on a rotary evaporator. The brown oil obtained (0.26 g) is purified by chromatography on a silica column (diameter: 1.5 cm, height: 30 cm), elution being carried out with a dichloromethane/methanol (95/5 by volume) mixture. The foamy product obtained is triturated with 5 ml of ethyl acetate, filtered and the solid is washed with ethyl acetate (2*5 ml) and dried at 50° C. under vacuum (1 mm Hg; 0.13 kPa). 0.07 g of 4-benzylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone is obtained in the form of an orange solid melting at 218° C. 4-Benzylcarbamoyl-2-bromo-1-indanone can be prepared in the following way:

According to the analysis of related databases, 33543-78-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); 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 492-98-8 as follows. Formula: C6H6N4

A mixture of CuCl22H2O (0.068 g, 0.40 mmol), K3[Fe(CN)6](0.099 g, 0.30 mmol) and 2,20-biimidazole (0.101 g, 0.75 mmol)in H2O (7 ml) was stirred for 15 min at room temperature,then sealed in a 15 ml Teflon-lined stainless steel containerand heated to 433 K for 6 d. After it had been cooled to roomtemperature at a rate of 10 K h1, red block-shaped crystalswere obtained in 40% yield (based on Cu). Analysis calculated(%) for C4H3CuN3, (I): C 30.67, H 1.93, N 26.82; found: C 30.46, H 1.85, N 26.95. IR (KBr, pellet, cm1): (N-H) 3448(w), (C-H) 3318 (w), (C N) 2108, 2042 (s), (C C andC N) 1526 (m).

According to the analysis of related databases, 492-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Qin, Ying-Lian; Sun, Hong; Jing, Yan; Jiang, Xiu-Ping; Wang, Gao-Feng; Qin, Jian-Fang; Acta Crystallographica Section C: Structural Chemistry; vol. 75; (2019); p. 1517 – 1523;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem