Category: imidazoles-derivatives

These common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, 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. Application In Synthesis of Imidazole-4-carbaldehyde

In the step (1) the resulting 1 H – imidazole -4 – formaldehyde reaction solution (0.229 muM) stirring cooling to 25 C, slowly adding hydroxylamine hydrochloride 19.1 g (0.275 muM), 1 H – imidazole -4 – formaldehyde, hydroxylamine hydrochloride in a molar ratio of 1: 1.2, temperature control 30 C, room temperature thermal insulation 2 hours, through the desolvation, shall be viscous […] 4 – a hydroxyimino imidazole (0.227 muM), yield 99%, direct synthesis of the next step.

The synthetic route of Imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian Qikai Pharmaceutical Technology Co., Ltd.; Han Xiaodong; Zhang Hongxue; Jiang Dianping; (6 pag.)CN109336820; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 693-98-1, These common heterocyclic compound, 693-98-1, name is 2-Methyl-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.

2-Methylimidazole (21) (925 mg, 11.27 mmol) was dissolved in THF (40 mL), cooled to 0 C and sodium hydride 60% in mineral oil (500 mg, 12.50 mmol) was added portion wise over 5 min. After 30 min of stirring at 0 C, 2-(trimethylsilyl)ethoxymethyl chloride (2.00 mL, 11.30 mmol) was added dropwise and the mixture was stirred at rt for 18 h. Purification by flash chromatography (SiO2, n-hexane/EtOAc 90:10 to 60:40) afforded 22 as a clear oil (2.30 g, 96%). 1H NMR (300 MHz, CDCl3) delta 0.02 (s, 9H),0.82e0.95 (m, 2H), 2.43 (s, 3H), 3.39-3.53 (m, 2H), 5.18 (s, 2H), 6.90(s, 2H).

The synthetic route of 693-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Heider, Fabian; Ansideri, Francesco; Tesch, Roberta; Pantsar, Tatu; Haun, Urs; Doering, Eva; Kudolo, Mark; Poso, Antti; Albrecht, Wolfgang; Laufer, Stefan A.; Koch, Pierre; European Journal of Medicinal Chemistry; vol. 175; (2019); p. 309 – 329;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89830-98-8, These common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-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 suspension of 7-iodo-6-methyl-3,4-dihydro-2H-isoquinolin-1-one (446.0 mg, 1.476 mmol), 4-cyclopropyl-1H-imidazole (218.4 mg, 1.919 mmol) in DMSO (2.5 mL) is added K2C03 (0.408 g, 2.952 mmol). The mixture is degassed with a stream of N2 for 5minutes. L-Proline (0.034 g, 0.295 mmol) and CuT (0.0562 g, 0.295 mmol) are added sequentially and the resulting mixture is stirred at 130 C for 5 hours under microwave conditions. The reaction mixture is slowly quenched with water (30 mL). The aqueous phase is extracted with EtOAc (2×80 mL) and washed with saturated brine (25 mL). The organic extracts are dried over Na2 SO4, filtered, and evaporated to dryness. The crude product is purified by silica gel flash chromatography, eluting with a gradient of 0% to 4% MeOH in DCM to give the title compound (0.198 g, 47.68%) as a white solid. ES/MS (m/z):268.0 (M+H).

Statistics shows that 5-Cyclopropyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 89830-98-8.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD; LEI, Hui; LIU, Gang; TIAN, Yuan; ZHANG, Haizhen; (0 pag.)WO2018/160406; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 96797-15-8,Some common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, molecular formula is C22H17IN2, 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.

A solution of 4-iodo-l-tritylimidazole (commercially available, 5.1 g, 1 1.8 mmol) in dichloromethane (40 ?iL) at -10 0C was treated with ethyl magnesium bromide (3.9 mL, 1 1.8 mmol, 3M in ether) and allowed to react for 45 m. A solution of 3-chloro-2-fluoro-benzaldehyde, (Intermediate 1) (1.5 g, 9.4 mmol) in dichloromethane was added via syringe at -10 0C and stirred for 16 hours at room temperature. The mixture was quenched with water (50 mL) and a saturated solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by MPLC with 3 to 5 % MeOHiCH2Cl2 to give (3-chloro-2-fluorophenyl)(l-trityl-l H-imidazol-4-yl) methanol, (Intermediate 2) as a solid, (3.5 g 78

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

Reference:
Patent; ALLERGAN, INC.; WO2008/141312; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 714273-83-3, A common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, molecular formula is C8H12N2O, 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.

1 g (6.5 mmol)5- (tert-Butyl) -1H-imidazole-4-carbaldehyde was added to 7 mL DMF followed by 2.59 g (13 mmol)N, N-diacetylpiperazine-2,5-dione nitrogen protection row of the third gas,3.19g (9.8mmol) of cesium carbonate was added and the atmosphere was purged with nitrogen for three times. The mixture was stirred for 20h at room temperature without light.The reaction mixture was poured into (100 mL) ice-water, suction filtered, the filter cake was washed with water (100mL * 2), petroleum ether:Ethyl acetate = 8: 1 (90 mL). The filter cake was ultrasonically dispersed with ethanol and methylene chloride. The insoluble material was filtered off and concentrated under reduced pressure. Absolute ethanol was taken in water.Further beating with ethyl acetate (50 mL).0.89g of a tan solid was obtained(Z) -1 -acetyl-3 – ((5- (tert-butyl) -1H-imidazol-4-yl) methylene) piperazine-2,5-dione in 46% yield.

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; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Li Wenbao; Wang Shixiao; Ding Zhongpeng; Hou Yingwei; Guan Huashi; (21 pag.)CN107011331; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 150058-27-8, These common heterocyclic compound, 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, 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.

Step 4. Under nitrogen atmosphere, bromide (1.0 mmol, 1.0 equiv.), methyl 2-ethoxy-1Hbenzo[d]imidazole-7-carboxylate (1.02 mmol, 1.02 equiv.), potassium carbonate (2.1 mmol, 2.1 equiv.)and a stirring bar were added into a 15 mL sealed glass tube. Then the Schlenk was sealed and DMF(6 mL) was injected by a syringe. The reaction was stired for 24 hr at room temperature. After thereaction was finished, the mixture was diluted with DCM (20 mL) and washed with water, and then thesolvent was removed under vacuum. The residue was purified with flash chromatography on silica gel(gradient eluent of petroleum ether/ ethyl acetate: 5:1) to give the methyl 1-((2′-(cyano-13C-15N)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate in 64% yield.

The synthetic route of 150058-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Hua; Dong, Yanan; Zheng, Chaonan; Sandoval, Christian A.; Wang, Xue; Makha, Mohamed; Li, Yuehui; Chem; vol. 4; 12; (2018); p. 2883 – 2893;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2034-22-2,Some common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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.

A mixture of 2,4,5-tribromo-1H-imidazole (120 g, 393.75 mmol, 1 equiv.), 1-(bromomethyl)-4-chlorobenzene (100 g, 486.67 mmol, 1.236 equiv.) and Cs2CO3 (200 g, 613.84 mmol, 1.559 equiv.) in DMF (1000 mL) was stirred at room temperature for 16 hours. To the reaction mixture was added EtOAc (500 mL) and H2O (300 mL). The organic layer was washed with H2O (2 X 300mL) and brine (300 mL), dried over anhydrous Na2SO4, filtered. The filtrate was concentrated to afford 2,4,5-tribromo-1-[(4-chlorophenyl)methyl]-1H-imidazole (170 g, crude) as a light yellow solid.

The synthetic route of 2034-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOLDFINCH BIO, INC.; DANIELS, Matthew, H.; YU, Maolin; HARMANGE, Jean-Christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; CASTLE, Neil, A.; MALOJCIC, Goran; (0 pag.)WO2019/173327; (2019); A1;,
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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Methyl-1H-imidazole-5-carbaldehyde

Example 18 rac-(3aR,14bR)-10-CyclohexyI-N7-(dimethylsulfamoyl)-13-methoxy-N3a,N3a- dimethyl-2-((l-methyl-lH-imidazol-5-yl)methyl)-l,2,3,14b-tetrahydroindolo[2,l~ a]pyrrolo[3,4-d][2]benzazepine-3a,7(4H)-dicarboxamide. 1 -Methyl- 1H-imidazole- 5-carbaldehyde (16.3 mg, 0.15 mmol) and then NaCNBH3 (9.3 mg, 0.15 mmol) were added to a slurry of rac-(3aR,14bR)- 10-cyclohexyl-N7-(dimethylsulfamoyl)- 13- methoxy-N3a,N3a-dimethyl-l,2,3,14b-tetrahydroindolo[2,1-alpha]pyrrolo[3,4-d][2]benzazepine-3a,7(4H)-dicarboxamide (30 mg, 0.049 mmol) in MeOH (2 mL). The reaction mixture was stirred at rt for 4h, diluted with THF (1 mL) and treated with additional 1 -methyl- 1H-imidazole-5-carbaldehyde (25 mg). The reaction mixture was stirred at rt for 16h, diluted with DMF (1 mL) and treated with additional NaCNBH3 (10 mg). The reaction mixture was stirred at rt for Id, diluted with MeOH, and purified by preparative HPLC (H2O/MeOH with 0.1% TFA buffer) to yield rac-(3aR,14bR)- 10-cyclohexyl-N7-(dimethylsulfamoyl)- 13-methoxy-N3a,N3a- dimethyl-2-((l -methyl- lH-imidazol-5-yl)methyl)-l ,2,3 , 14b-tetrahydroindolo[2, 1 – alpha]pyrrolo[3,4-d] [2]benzazepine-3a,7(4H)-dicarboxamide (20.2 mg, 0.029 mmol, 58% yield) as a white solid. 1H NMR (300 MHz, CD3OD) delta 1.25 – 1.65 (m, 4H), 1.77 – 2.23 (m, 7H), 2.66 (d, J= 10.6 Hz, IH), 2.94 – 3.07 (m, 2H), 3.05 (s, 6H), 3.10 – 3.35 (m, 6H), 3.51 (d, J= 15.0 Hz, IH), 3.58 (d, J= 15.0 Hz, IH), 3.64 (s, 3H), 3.79 (d,J = 10.6 Hz, IH), 3.91 (s, 3H), 4.04 (d, J= 15.0 Hz, IH), 4.15 (dd, J= 10.6, 7.7 Hz, IH), 4.52 (d, J= 15.0 Hz, IH), 7.06 – 7.15 (m, 3H), 7.41 (d, J= 8.4 Hz, IH), 7.65 (dd, J= 8.4, 1.5 Hz, IH), 7.95 (d, J= 8.4 Hz, IH), 8.03 (d, J= 1.5 Hz, IH), 8.55 (br s, IH). LCMS: m/e 702 (M+H)+, ret time 3.16 min, 4 minute gradient.

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/120733; (2009); 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 1122-28-7 as follows. name: 4,5-Dicyanoimidazole

Example 19 2-Bromo-4,5-dicyanoimidazole (21) To 1.18 g (10 mmol) 4,5-dicyanoimidazole and 25 ml 0.1 M NaOH was added 1.8 ml Br2 (35 mmol). The mixture was stirred overnight at room temperature and then acidified with dilute HCl. The solid was filtered, rinsed with water and recrystallized from water to give 1.5 g of dicyanobromoimidazole 21 (yield 76.4%).: m.p. 147-149 C.(lit. 141-143 C.); Rf=0.65 (ethyl acetate_methanol=4:1); MS(EI): 198([M+2], 96%), 196 ([M+], 100%),171 (28.5), 169 (29.2), 117 (27.4), 91 (19.0), 64 (20.6), 53 (22.4), 38 (18.8).

According to the analysis of related databases, 1122-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; McGill University; US6476216; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 muM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H2O (1.0 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into an oil bath, which was preheated to 70 C (90 C for alkyl amine, 120 C for imidazole). The reaction mixture was stirred for another 16 h (8 h for imidazole). After allowing the mixture to cool to room temperature, the reaction mixture was filtrated, the precipitates were washed with water and ethyl acetate thoroughly. The filtrate was extracted with ethyl acetate (3¡Á25 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel to afford the desired products.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Liye; Yu, Ruina; Zhu, Xinhai; Wan, Yiqian; Tetrahedron; vol. 69; 42; (2013); p. 8974 – 8977;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem