Category: imidazoles-derivatives

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 3034-41-1 as follows. name: 1-Methyl-4-nitroimidazole

To the suspension of 1-methyl-4-nitro-1H-imidazole (128 mg, 1.012 mmol) in ethanol (5 mL) 5% palladium on carbon (10 mg, 0.053 mmol) was added. The reaction mixture was degassed under reduced pressure and stirred under hydrogen atmosphere at roomtemperature for 3 hours. The reaction mixture was filtered over celite layer and washed with ethanol. The filtrate was concentrated under reduced pressure, dissolved in toluene, transferred to a Schlenk flask and again concentrated under reduced pressure. 4-(5-Chloro- 3 -(4-chloro-2-fluorobenzyl)-2-methylpyrazolo [1, 5-a]pirymidyn-7-yl)morpholine obtained in Example 1, Step F (200 mg, 0.506 mmol), tris(dibenzylideneacetone)dipalladium(0)(23.2 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene (29,3 mg, 0,05 1 mmol) and sodium carbonate (107 mg, 1.012 mmol) were added and the mixture was degassed under reduced pressure. Under argon atmosphere degassed toluene (5 mL) was added and the mixture was purged with argon for 15 minutes. Reaction mixture was heated to 100 C for 24 hours. The mixture was cooled to room temperature, diluted with ethylacetate (10 mL), filtered through celite layer and washed with ethyl acetate (25 mL). The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silicagel, eluent: AcOEt 100% to AcOEt:methanol = 9:1, v/v). The product was hot-crystallized from AcOEt:heptan to obtain white crystals with a yield of 27% (63 mg, 0.138 mmol).

According to the analysis of related databases, 3034-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELON PHARMA S.A.; MROCZKIEWICZ, Michal; LIPNER, Joanna; GUNERKA, Pawel; DUBIEL, Krzysztof; WIECZOREK, Maciej; ZDZALIK, Daria; STANCZAK, Aleksandra; LAMPARSKA-PRZYBYSZ, Monika; STYPIK, Bartosz; WO2015/118434; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 103057-10-9, 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. 103057-10-9 name is 4-(Chloromethyl)-1-trityl-1H-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.

REFERENCE EXAMPLE 34 Ethyl 5,6-Dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-carboxylate In 5000 ml of dimethyl sulfoxide was suspended 250.2 g of ethyl 5,6-dimethoxyindazole-3-carboxylate, and 40.2 g of lithium methoxide was added to the suspension, followed by stirring at room temperature for 1 hour. A solution of 447.8 g of 4-chloromethyl-1-tritylimidazole in 2000 ml of dimethyl sulfoxide was added dropwise thereto at room temperature over 10 minutes. After stirring at room temperature for 2 hours, 4.2 g of lithium methoxide and 44.8 g of 4-chloromethyl-1-tritylimidazole were further added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into 30000 ml of ice-water while stirring. A precipitated crystal was collected, washed with three 2000 ml portions of water, and dried. The solid was dissolved in 10000 ml of chloroform, and the solution was dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform:ethanol=50:1) and recrystallized from chloroform/isopropyl alcohol to yield 222.0 g of the title compound as a colorless prism crystal. Melting point: 184-186 C.; IR (KBr) cm-1: 1704, 1496, 1268, 1146, 1132, 1092, 748, 700; 1 H-NMR (CDCl3) delta ppm: 1.21 (6H, d, J=5.9 Hz, Me of iso-PrOH), 1.46 (3H, t, J=7.3 Hz), 3.93 (3H, s), 3.97 (3H, s), 4.01 (1H, m, CH of iso-PrOH), 4.49 (2H, q, J=7.3 Hz), 5.61 (2H, s), 6.79 (1H, s), 7.03 (5H, m), 7.13 (1H, s), 7.28 (10H, m), 7.47 (1H, s), 7.51 (1H, s); Elementary analysis for C35 H32 N4 O4.C3 H8 O: Calcd. (%): C 72.13; H 6.37; N 8.85; Found (%): C 71.53; H 6.37; N 8.70.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Chloromethyl)-1-trityl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Pharmaceutical Co., Ltd.; US5681954; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 131020-36-5, name is Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate

The methyl 1-methyl-1H-benzimidazole-5-carbonate (500 mg) obtained above was dissolved in methanol (10 ml). 1 N Sodium hydroxide solution (8 ml) was added thereto, and the mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture which was then acidified by formic acid. Precipitates were collected by filtration and dried under reduced pressure to give the title compound (367 mg, Y.: 79%). 1H NMR; (DMSO-d6) delta (ppm): 3.8 (s, 3H), 7.6 (d, 1H), 7.8 (dd, 1H), 8.2 (d, 1H), 8.3 (s, 1H).

The synthetic route of 131020-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; EP1595866; (2005); 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 24134-09-6 as follows. COA of Formula: C5H7BrN2

n-BuLi (2.66 M in hexanes, 0.963 mL, 2.56 mmol) was added dropwise to a stirred slurry of 5-bromo-1,2-dimethyl-1H-imidazole (470 mg, 2.68 mmol) in THF (7 mL) at ?-70 C. under argon. After stirring for another 7 minutes, the slurry was treated dropwise over 5 minutes with a solution of methyl 4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline-6-carboxylate (500 mg, 1.22 mmol, Intermediate 75) in THF (6 mL). The reaction was stirred in the dry ice/acetone bath for another 10 minutes, then removed from the cold bath and stirred for 6 minutes, then stirred in an ice bath for 2 minutes, then quenched with 5 M aqueous NH4Cl (0.77 mL, 3.85 mmol) to give an orange solution. The reaction mixture was dried (Na2SO4), filtered, and concentrated to dryness. The residue was purified by silica flash column chromatography (0-10% MeOH/DCM) to provide the title compound.

According to the analysis of related databases, 24134-09-6, the application of this compound in the production field has become more and more popular.

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; US2015/105366; (2015); 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Example 1[51] Synthesis of 4-methyl-N-[3-(4-methylimidazole-l-yl)-5-trifluoromethyl-phenyl] -3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzamide [52][53] Method A[54] In a reactor, potassium tert-butoxide (20.9g, 186.56mmol) was dissolved in tetrahydrofuran (167ml), and then was cooled to -20+50C. To the resultant product, 3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) dissolved in tetrahydrofuran (80ml) was added and stirred for 30 minutes. When the stirring was completed, 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester (15.5g, 45.60mmol) dissolved in tetrahydrofuran (90ml) was slowly added to the resultant product. After the addition, the temperature of the mixture was slowly elevated to room temperature, and stirring was carried out until the reaction was completed. When the reaction was completed, the reaction mixture was cooled to 5-1O0C, and then 15% sodium chloride aqueous solution (337ml) was slowly added to the reaction mixture. After the addition, the temperature of the reaction mixture was slowly elevated to room temperature again, and then water (170ml) was added thereto and an organic layer was extracted and separated.[55] To the organic layer, ethyl acetate (400ml) was added. Then, the layer was washed with water (200ml), separated and was subjected to vacuum concentration. When the concentration was completed, methanol (220ml) was added thereto. Then, the resultant layer was subjected to reflux- stirring for 1 hour, cooled to room temperature, and then stirred for 2 hours.[56] The obtained solid was filtered, sufficiently washed with methanol (100ml), and then dried to provide a pale yellow solid final compound (17.51g, yield 81%).[57] 1H-NMR(DMSOd6, delta= 2.19(s,3H), 2.36(s,3H), 7.24(s,lH), 7.35(m,2H), 7.47 (s,lH),7.64(d,lH), 7.71(d,lH), 7.92(d,lH), 8.01(s,lH), 8.11(s,lH), 8.30(s,2H), 8.47(d,lH), 9.00(s, IH), 10.49(s,lH)

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; KIM, Dong Yeon; CHO, Dae Jin; LEE, Gong Yeal; KIM, Hong Youb; WOO, Seok Hun; WO2010/18895; (2010); 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. 1849-02-1, name is 2-Chloro-1-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1849-02-1

EXAMPLE 39; CYCLOHEXYL-ETHYL- {2- [4- (1-METHYL-1 H-BENZOIMIDAZOL-2-YLOXY)-PHENYL]-ETHYL}- amine; A mixture of 4- [2- (cyclohexyl-ethyl-amino)-ethyl]-phenol (247 mg, 1.0 MMOL), N- methyl benzimidazole (EXAMPLE 8 ; 200 mg, 1.2 MMOL), and CS2CO3 (652 mg, 2.0 MMOL) in DMF (3 mL) was stirred at 100 C for 16 h. The reaction mixture was cooled and filtered through diatomaceous earth, which was then washed with ethyl acetate (30 mL). The combined filtrates were washed with H20 (3 x 10 mL) then brine (10 mL), dried (NA2SO4), filtered, and concentrated under reduced pressure. The crude material was purified on SI02 (10 g; 0-100% 10% [2 M NH3 in CH30H] in CH2CI2/CH2C12) to provide 105 mg (28% yield) of a brown oil. MS (ESI) : mass calculated for C24H3INSO, 377.53 ; M/Z FOUND, 378.4 [M+H] +. H NMR (400 MHz, CDC13) : 7.52 (d, J =7. 2, 1 H), 7.63-7. 58 (m, 1 H), 7.33-7. 18 (m, 7H), 3.75 (s, 3H), 2.81-2. 70, m, 4H), 2.68 (q, J = 7.1, 2H), 2.60- 2.50 (m, 1H), 1. 90-1. 80 (m, 4H), 1.67 (d, J : = 12.3, 1 H), 1.35-1. 18 (m, 4H), 1.15-1. 05 (m, 1H), 1.12 (t, J=7. 1, 3H)

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 1849-02-1.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/12296; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24134-09-6, 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 163: 4-(1 ,2-dimethyl-1 H-imidazol-5-yl)aniline; [00335] Tetrakis(triphenylphosphine)palladium (0.053g, 0.046mmol) was added to a solution of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (0.1 g, 0.456mmol), 5- bromo-1 ,2-dimethyl-1 /-/-imidazole (0.088g, 0.502mmol) and cesium fluoride (0.208g, 1 .369mmol) in DME/MeOH (2/1 , 2.9ml_). The reaction mixture was heated for 10 minutes at ~ 50 C under microwave irradiation. The reaction was diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified using Biotage silica gel column chromatography eluting with 1 to 5% MeOH/aq. NH3 (10/1 ) in DCM followed by filtration through a SCX-2 column to afford the title product as a white solid (48mg, 56%).1 H NMR (500MHz, CDCI3): delta 2.42 (s, 3H), 3.46 (s, 3H), 3.81 (br s, 2H), 6.71 -6.74 (m, 1 H), 6.85 (s, 1 H), 7.12-7.14 (m, 1 H).LC (Method B)-MS (ESI, m/z) fR 0.24 min, 188 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1,2-dimethyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 113775-47-6, name is Dexmedetomidine, 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. Computed Properties of C13H16N2

L- (+) – tartaric acid (9 g, 60 mmol)Was added to a solution of metomidol (12 g, 60 mmol) in ethanol (250 ml).The suspension was heated to reflux until complete dissolution,Followed by stirring at room temperature overnight,Filtration gave a white solid (9 g).The resulting solid was heated to reflux in isopropanol (200 ml)Followed by stirring at room temperature overnight,Filtration gave (13.5 g).The obtained solid was purified once more in the same manner,To obtain a solid 8. lg, purity 99.9%, yield 77.1%.

The synthetic route of Dexmedetomidine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co; Hou, Xianshan; Wang, Junyan; Wang, Zhian; Zhong, Xinguang; (11 pag.)CN106083724; (2016); 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 1403474-70-3 as follows. Application In Synthesis of Ethyl 2-ethoxy-1-((2′-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Example 2 Preparation of the product 2-Ethoxy-3- [2 ‘- (5-oxo-4,5-dihydro- [1,2,4] oxadiazol-3-yl) 4-ylmethyl] -3H-benzimidazole-4-carboxylate 55.1 g,0.4 MN NaOH into the reaction bottle,75 C stirring reaction to the raw material reaction is completed. The reaction solution was cooled to room temperature. The filtrate was added with 820ml of absolute ethanol, filtered and kept at 20 C. The pH was adjusted to 1 with 2M HC1 solution. A large amount of solid was precipitated, stirred for 1 hour, filtered and washed with water. 50.6 g,HPL (^ i ^ S 98.6%

According to the analysis of related databases, 1403474-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hunan Xianjin Xiangjiang Pharmaceutical co., LTD; YUAN, XIUJU; YAO, LIANGYUAN; ZONG, AIJUN; DENG, MENGRU; (12 pag.)CN103664921; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1467-16-9, 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. 1467-16-9, name is 1H-Imidazole hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 7 11beta-fluoro-17-(5-fluoropyridin-3-yl)oestra-1,3,5(10),16-tetraene-3-carboxamide 100 mg of (11beta)-11-fluoro-17-(5-fluoropyridin-3-yl)oestra-1,3,5(10),16-tetraene-3-carboxylic acid were initially charged in 3 ml of 2-methyltetrahydrofuran, then 62 mg (1.5 equiv.) of 1,1′-carbonyldiimidazole and 13 mg of imidazole hydrochloride were added and the mixture was stirred at room temp. for 18 h. Then 597 mul of 25% aqueous ammonia solution were added and the mixture was stirred at room temp. for 3 hours, admixed with 10 ml of 1M hydrochloric acid solution, extracted three times with ethyl acetate, concentrated and purified by preparative HPLC. Yield: 51 mg of the title compound. C24H24F2N2O UPLC analysis (Method 1) Rt=1.22 mass found ESI(+) 394.19. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.14 (s, 3H), 1.40-1.55 (m, 1H), 1.73-2.03 (m, 4H), 2.13-2.25 (m, 1H), 2.27-2.38 (m, 1H), 2.50-2.60 (m, 1H), 2.67 (dd, 1H), 2.80-2.97 (m, 2H), 5.60-5.81 (1H), 6.30 (br. s., 1H), 7.22 (br. s., 1H), 7.40 (d, 1H), 7.55-7.63 (m, 2H), 7.71 (dt, 1H), 7.85 (s, 1H), 8.45 (d, 1H), 8.48-8.55 (m, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BOTHE, Ulrich; BUSEMANN, Matthias; BARAK, Naomi; ROTGERI, Andrea; FISCHER, Oliver Martin; MARQUARDT, Tobias; (41 pag.)US2016/24142; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem