Category: imidazoles-derivatives

Application of 28890-99-5,Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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.

b) Compound 7-1 (3.0 g, 7.0 mmol), benzimidazolo[1,2-a]benzimidazole (1.8 g, 8.4 mmol), and potassium phosphate (3.6 g, 29.8 mmol) were added to NMP (35 mL). The mixture was stirred at 190 C for 8 h. After reaction mixture was cooled at room temperature, it was diluted with 40 mL of water to give a solid. The solid was collected by filtration, and it was washed with 100 mL of water. The crude product was purified by by column chromatog20 raphy on silica gel eluting with toluene to yield 2.5 g (58%) of compound B-17 as a whitesolid. LC-MS (mlz) 615 [M+H]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; NISHIMAE, Yuichi; KOHLSTEDT, Julia; SCHAeFER, Thomas; NAGASHIMA, Hideaki; (114 pag.)WO2016/97983; (2016); 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 2034-22-2 as follows. Safety of 2,4,5-Tribromoimidazole

Step 1: N-(2.4.5-tribromo-l-(r2-(trimethylsilv?ethoxy1methyl|-lH-imidazole (A1); To a solution of 2,4,5-tribromo-imidazole in THF was added portionwise sodium hydride (1 eq.). The mixture was stirred for 20 min at RT and SEM-Cl (1 eq.) was added. The mixture was left stirring for 16 h at RT. After dilution with Et2O the suspension was filtered and the clear solution was concentrated to dryness under reduced pressure. The oily residue was dissolved in PE/ 5% EtOAc and applied on a silicagel column. After washing with PE/ 5% EtOAc the product was eluted with PE/ 10% EtOAc. The solvents were removed under vacuum to afford the title compound as a white solid. 1U NMR (400 MHz, CDCl3) delta: 5.31 (s, 2H), 3.59 (t, J=7.8 Hz, 2H), 0.92 (t, J=7.8 Hz, 2H), 0.01 (s, 9H).

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; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2008/56187; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 137049-00-4, 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. 137049-00-4 name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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.

To methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate (Step 6, Example 1) (1.0 equiv) and Et3N (3.0 equiv) or pyridine (3.0 equiv) in CH2Cl2 (0.05 M) was added 1-methylimidazole-4-sulfonyl chloride (1.2 equiv). The reaction was monitored by TLC (10% MeOH-CH2Cl2) and was heated if necessary. After 30 min the mixture was poured into saturated sodium bicarbonate and extracted with CH2Cl2. The combined organic phase was washed with brine, dried over sodium sulfate and purified by column chromatography to afford 92% of the desired product.

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

Reference:
Patent; Wyeth; US2008/9485; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-methyl-2-n-propyl-1H-benzimidazole-6-carboxylic (1, 2.18g, 10mmol) and thionyl chloride (20mL, 280mmol) was refluxed for 3h, then the excess thionyl chloride was removed under reduced pressure to obtain the crude acyl chloride (2) as an off-white solid. It was used for the next step directly.

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jun; Wang, Jin-Liang; Yu, Wei-Fa; Zhou, Zhi-Ming; Tao, Wen-Chang; Wang, Yi-Cheng; Xue, Wei-Zhe; Xu, Di; Hao, Li-Ping; Han, Xiao-Feng; Fei, Fan; Liu, Ting; Liang, Ai-Hua; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 44 – 54;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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

Synthetic Route of 52099-72-6,Some common heterocyclic compound, 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C10H10N2O, 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.

Compound III-1 (1.74 g, 10 mmol) represented by the following structural formulaPotassium carbonate (2.74 g), 1,4-dibromopropane (6.07 g, 30 mmol) was added to a solution of (20 ml) in DMF for 3 hours,Stir at 60 C. Water was added to the reaction solution, and extracted with ethyl acetate.The organic layer was washed with brine and dried over Na 2 SO 4. Filtration,After evaporation of the solvent, the residue is subjected to silica gel column chromatographyPurification by (AcOEt / n-hexane 1: 4) gave compound III-2 (1.961 g, 66%) as a colorless oil.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Medical and Dental University; Hata, Yutaka; Kagechika, Hiroyuki; Ito, Shigeru; Tsuemoto, Nozomi; kodaka, Manami; Dilihumaer, Ainiwaer; (24 pag.)JP2019/89720; (2019); A;,
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. 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, A new synthetic method of this compound is introduced below., Formula: C7H8N2O4

lH-Imidazole-4,5-dicarboxylic acid dimethyl ester (592 mg, 3.21 mmol) is combined with hydrazine (600 mg, 18.8 mmol) and MeOH (10 mL). The reaction mixture is heated to 115C for 30 min. Cool and filter off the resulting precipitate. Wash with additional water. Combine the precipitate with hydrazine (1.38 mL) and reflux for 4 h. Pour the reaction mixture into ice water and adjust the to pH 2 with HCl (12 N). The new precipitate is isolated by filtration to afford the title product (293 mg, 60%) 1H NMR (400 MHz, DMSO-^6) delta 11.41 (br. s., 1.47 H), 8.27 (s, 1 H), 3.37 (br. s., 6.2 2H).

The synthetic route of 3304-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-18-6, The chemical industry reduces the impact on the environment during synthesis 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, I believe this compound will play a more active role in future production and life.

Synthesis of (Z)-(S)-4-[(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]-2-[1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene]-6-methylmorpholin-3-one In nitrogen atmosphere, an acetonitrile solution (4 mL) of (S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methyl-morpholin-3-one (92 mg) and triphenylphosphine hydrobromide (68 mg) was heated under reflux for 1 hr. The solvent of the reaction solution was evaporated under reduced pressure. To an ethanol solution (4 mL) of the obtained residue, 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (40 mg) and TEA (0.12 mL) were added. The resulting reaction solution was stirred in nitrogen atmosphere at room temperature overnight and then concentrated under reduced pressure. To the obtained residue, trifluoroacetic acid (1 mL) was added. The resulting reaction solution was stirred at room temperature for 2 hr and then poured into a saturated sodium hydrogencarbonate aqueous solution. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and then with saturated saline and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluding solvent; heptane:ethyl acetate=1:1 to 0:1) to give 61.9 mg of the title compound. The physical property values of this compound were as follows: ESI-MS; m/z 502 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.33 (d, J=6.0 Hz, 3H), 1.42 (d, J=6.0 Hz, 3H), 2.34 (s, 3H), 3.20 (dd, J=9.6, 12.8 Hz, 1H), 3.61 (dd, J=2.4, 12.8 Hz, 1H), 3.85 (s, 3H), 4.42-4.52 (m, 2H), 5.35 (d, J=6.8 Hz, 1H), 6.85 (s, 1H), 6.95 (s, 1H), 7.06-7.15 (m, 2H), 7.22 (d, J=8.0 Hz, 1H), 7.33 (dd, J=1.6, 8.0 Hz, 1H), 7.53 (d, J=1.6 Hz, 1H), 7.86 (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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2009/48213; (2009); 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. 1072-62-4, name is 2-Ethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1072-62-4

In an argon stream, 2-ethylimidazole (1.92 g, 20 mmol) and sodium hydride (0.84 g, 21 mmol) were suspended in tetrahydrofuran (30 mL) and cooled to 0 C. 1-Iodohexane (4.67 g, 22 mmol) was added to the suspension, and the mixture was stirred at room temperature for 30 minutes and then at 75 C. for 24 hours. After standing to cool, diethyl ether and water were added to the reaction mixture, the organic layer was extracted, and the organic layer was washed with brine. After adding sodium sulfate to the organic layer and stirring, the solid was filtered off and the solvent was distilled off. The resulting oily substance was purified by silica gel column chromatography (chloroform / methanol = 10: 1) to obtain 1-hexyl-2-ethylimidazole as a yellow oily substance (2.93 g, 81%).

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 1072-62-4.

Reference:
Patent; Tosoh Corporation; Sagami Chemical Research Institute; Aihara, Hidenori; Yamagata, Takuya; Hachiya, Hitoshi; Watanabe, Makoto; Fukuda, Takashi; Ueda, Saori; Miyashita, Masato; (64 pag.)JP2018/168149; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1615-14-1, These common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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.

Synthesis of 10-(2-(1H-Imidazol-1-yl)ethyl) 2-benzyl (25,4a5,6a5,6bR,8a5, 105, 12a5, l2bR, l4bR)-2,4a,6a,6b,9,9, 12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9, 10, 11, 12, 12a, 1 2b, 13,1 4b-icosahydropicene-2, 1 0-dicarboxylate (7-1). Into a 25 -mL round-bottom flask, wasplaced 1-7 (137 mg, 0.23 mmol, 1.00 equiv.), DCM (10 mL), 2-(1H-imidazol-1-yl)ethan-1-ol (51 mg, 0.45 mmol, 2.00 equiv.), DMAP (3 mg, 0.02 mmol, 0.10 equiv.), TEA (0.047 mL, 1.50 equiv.). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with DCMIMeOH(20:1). This resulted in 140mg (91%) of 7-1 as a white solid.

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem