Category: imidazoles-derivatives

These common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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. HPLC of Formula: C12H12N2O2

Under ice-cooling, L-selectride (4.52 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (30 mL) solution containing (4R,6S)-6-(4-fluorophenyl)-1,1-dimethyltetrahydropyrrolo[2,1-c][1,4]oxazine-3,4-dione (1.03 g). Stirring was continued for 1 hour at the same temperature. A 5 N sodium hydroxide aqueous solution (686 muL) was added to the reaction solution, and stirring was continued for 20 minutes at 0 C., and next hydrogen peroxide solution (333 muL, 35% aqueous solution) was added, and stirring was continued for 20 minutes at 0 C. Sodium bisulfite (356 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine was added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (30 mL) and triphenyl phosphonium bromide (1.2 g) were added to the residue, and the resultant was heated under reflux for 1 hour. The resultant was cooled to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (817 mg) and triethylamine (951 muL) was added, and stirring was continued for 10 hours at room temperature. The solvent was removed under a vacuum, and ethyl acetate and brine were added, and the organic layer was partitioned. The resultant was dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum. Crude purification of the residue was conducted by silica gel column chromatography (carrier: Chromatrex NH, eluting solvent: hexane/ethyl acetate?ethyl acetate?ethyl acetate/methanol). The resulting solid was suspended in ethyl acetate, and diethyl ether was added, and the resultant was left overnight at 4 C. By filtering, the title compound (860 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 462 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.45 (s, 3H), 1.58 (s, 3H), 1.82-1.93 (m, 1H), 2.02-2.14 (m, 2H), 2.29 (s, 3H), 2.33-2.44 (m, 1H), 3.84 (s, 3H), 3*94 (dd, J=12.0, 5.2 Hz, 1H), 5.16 (d, J=9.6 Hz, 1H), 6.77 (s, 1H), 6.91 (dd, J=1.2, 1.2 Hz, 1H), 6.98-7.03 (m, 2H), 7.17 (d, J=8.4 Hz, 1H), 7.28-7.31 (m, 3H), 7.53 (d, J=2.0 Hz, 1H), 7.69 (d, J=1.2 Hz, 1H).

The synthetic route of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

The starting material was prepared as follows: Diethyl azodicarboxylate (160 mg, 1.4 mmol) was added to a solution of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (261 mg, 0.7 mmol), (prepared as described for the starting material in Example 22), triphenylphosphine (367 mg, 1.4 mmol) and 2-(imidazol-1-yl)ethanol (94 mg, 0.84 mmol), (J. Med. Chem. 1993, 25, 4052-4060), in methylene chloride (5 ml) and the mixture stirred for 1 hour at ambient temperature. Acetic acid (42 mg, 0.7 mmol) was added and the solvent was removed by evaporation. The residue was triturated with ether, the solid collected by filtration, dried under vacuum and purified by chromatography eluding with methylene chloride/methanol (9/1 followed by 8/2) to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (250 mg, 76%).

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

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-88-1, name is 5-Bromo-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. Formula: C7H5BrN2

[00586] A. tert-Buty 5-bromo-lH-benzo[d]imidazole-2-carboxyIate. A solution of 5-bromo-lH-benzimidazole (1.06 g, 5.38 mmol), di-tert-butyl dicarbonate (1.3 g, 5.91 mmol), triethylamine (0.9 mL, 6.45 mmol) and dimethylaminopyridine (few crystals) in anhydrous tetrahydrofuran (15 mL) was allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by Biotage chromatography (0-55% ethyl acetate in hexanes) to provide the desired product (0.85 g, 54%) as a white solid. MS (ESI) m/z 297.3 [M+l]+.

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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: (I) 1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose (3)(1.0 g; 4.0 mmol) was dissolved in DMF (20 ml), cooledat 0 C and under N2-atmosphere NaH (0.14 g; 6.0 mmol)was added to the solution. The suspension was stirred for30 min and cooled to -35 to -40 C. After N?,N-sulfonyldiimidazole(1.2 g; 6.0 mmol) in DMF (12 ml) was droppedto the reaction mixture and stirred for 30 min again at-40 C. MeOH was added (0.8 ml) to the solution andstirred for 30 min at -40 C. The solution was poured intoice-water (200 ml). The precipitate was filtered, washedwith cold water to get the white crystalline product 11(1.2 g; 80%). M.p.: 97-98 C; lit. m.p. (Vatle and Hanessian1996): 98-99 C; Rf = 0.70 (EtOAc-hexane 1:1).(II) From 3 (25.0 g; 96.0 mmol) the yield was 84% (31.5 g).

The synthetic route of 7189-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagy, Adrienn; Csordas, Barbara; Zsoldos-Mady, Virag; Pinter, Istvan; Farkas, Viktor; Perczel, Andras; Amino Acids; vol. 49; 2; (2017); p. 223 – 240;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, belongs to imidazoles-derivatives compound, 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 3304-70-9, COA of Formula: C7H8N2O4

1H-Imidazole-4,5-dicarboxylic acid dimethyl ester (1.5 g, 8.15 mmol, 1 equiv. ) was dissolved in MeOH (10 mL) and benzyl bromide (1.16 mL, 9.77 mmol, 1.1 equiv.) before sodium hydride (360 mg, 1.1 equiv., 60% dispersion) and sodium iodide (200 mg) was added. The reaction was stirred for 16 hours before being quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (2 x 30 mL) and the organic layer washed several times with water (4 x 30 mL), brine solution (50 mL). It was dried over Na2S04, filtered and concentrated in vacuo. 1-Benzyl-1H- imidazole-4,5-dicarboxylic acid dimethyl ester 254 (2.01 g, 90 %, 7.33 mmol). ¹H NMR (300 MHz) CDC13 No. 7.58 (s, 1 H), 7.33 – 7.42 (m, 3 H), 7.14 – 7.18 (m, 2 H), 5.41 (s, 2 H), 3.92 (s, 3 H), 3.84 (s, 3 H). MS: 275.1 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl 4,5-imidazoledicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong, R.; CHEN, Xiaowu; FARDIS, Maria; JABRI, Salman, Y.; JIN, Haolun; KIM, Choung, U.; METOBO, Sanuel, E.; MISH, Michael, R.; PASTOR, Richard, M.; WO2005/117904; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, 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. 288-32-4 name is 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.

To a mixture of 1H-Imidazole (50 g, 0.73 mol) in DMF (200 mL) was added NIS (328 g, 1.46 mol) portionwise, the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was poured in sat. Na2CO3 solution, filtered, the residue was washed with water and dried to give 150 g of 2,4,5-triiodo-1H-imidazole (Yield=46%).

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

Reference:
Patent; Genentech, Inc.; US2012/245144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, belongs to imidazoles-derivatives compound, 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 147403-65-4, Recommanded Product: Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Example 4Methyl 2-ethoxy- 1 -((2′-(5-oxo-4,5-dihydro- 1 (2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- 1H- benzo[< ]imidazole-7-carboxylate of formula la l ,8-Diazabicyclo[5.4.0.]undec-7-ene (DBU; 0.1 g, 0.65 mmol) was added dropwise to a mixture of methyl 2-methoxy- l -((2'-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)- lH- benzo[i ]imidazole-7-carboxylate (of formula Va; 0.22 g, 0.5 mmol), the corresponding solvent (3 ml) and carbonyldiimidazole (0.1 g, 0.6 mmol) in a reaction vial under stirring and the mixture was stirred at the room temperature for 3 hours. Then, the content of the vial was poured into water ( 10 ml) and, after acidification with acetic acid, the separated solids were aspirated and washed with water. The yields and purity of the products are summarized in Table I. Table I - Yield and purity of the product of Example 4* - Also contains 40.4 % of the starting compound of formula Va; ** - Carbonyl-di- 1 ,2,4- triazole was used instead of carbonyldiimidazole. 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, Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ZENTIVA, K.S.; RADL, Stanislav; WO2012/139536; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2851-13-0, name is N,N-Dimethyl-1H-benzo[d]imidazol-2-amine, molecular formula is C9H11N3, 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. Recommanded Product: 2851-13-0

Scheme 3 exemplifies a method of forming compounds of Formula I. Chloro purines (4) (1 mmol) can be coupled with R3-H (for example, wherein R3 is benzimidazol-1-yl) (1.03-1.30 mmol), under Buchwald conditions, for example tris(dibenzylideneacetone)-dipalladium(0) (0.02-0.05 mmol), XPhos (0.10-0.20 mmol), cesium carbonate (2 mmol) in DMF (7-10 mL) with heating under microwave at 140-150 C. for 30 minutes to form purines of Formula I. Formula I purines can be further purified by diluting with EtOAc, filtering the contents of the reaction, concentrating and purifying with flash chromatography or reverse phase HPLC. Formula I purines can be further derivatized in subsequent transformations to functionalize R1, for example by deprotecting any protected functional groups (for example deprotecting BOC-protected amine groups followed by additional steps, such as reductive amination, amide coupling or acylation to form additional compounds of Formula I.Example 131 1-(3-(2-(2-(dimethylamino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one 131 The compound was prepared from 1-(3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one and N,N-dimethyl-1H-benzo[d]imidazol-2-amine following General Procedure of Buchwald coupling shown in Scheme 3. 1H NMR (400 MHz, CDCl3) delta 8.29 (s, OH), 7.58 (d, J=7.5 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.15 (dd, J=11.0, 4.3 Hz, 1H), 7.01 (dd, J=10.1, 4.2 Hz, 1H), 5.58-5.45 (m, 1H), 4.60 (d, J=7.2 Hz, 2H), 4.53-4.39 (m, 2H), 4.31 (d, J=9.6 Hz, 1H), 4.19 (s, 5H), 3.88-3.74 (m, 4H), 3.65 (s, 2H), 3.60 (s, 1H), 3.17 (s, 1H), 2.98 (s, 4H), 2.56-2.42 (m, 1H), 1.14 (d, J=6.8 Hz, 5H). LCMS: M+H+=520.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2851-13-0, its application will become more common.

Reference:
Patent; Li, Jun; Safina, Brian; Sutherlin, Daniel P.; Sweeney, Zachary; US2012/15931; (2012); 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,1′-Thiocarbonyldiimidazole

A solution of (2R)-3-PHENYL-1-PIVALOYLOXY-2-PROPYL amine (19-1, LMMOL) and ET3N (1 mmol) in DMF (1 mL) was added dropwise into the pre-dissolved solution of 1,1- thiocarbonyl diimidazole (1.2 mmol) in DMF (2 mL) at 50 C over 1 min. The mixture was stirred for 1 min. at 50 C and then for 10 min. at room temperature. The mixture was directly purified by column chromatography using EtOAc: hexanes (1: 5) as eluant to afford (2R)-3-phenyl-1-pivaloyloxy-2-propyl isothiocyanate (19-3, SU-684). 89% yield, colorless oil. H NMR (CDC13) 5 7.15-7. 35 (M, 5 H), 4.22 (dd, 1 H, J= 2. 7,10 Hz), 4.02-4. 12 (m, 2 H), 2.94 (d, 2 H, J= 6. 3 HZ), 1.25 (s, 9 H)

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIGITALBIOTECH CO., LTD.; WO2005/3084; (2005); 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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 1-Decyl-1H-imidazole

General procedure: A solution of 1,3-propane sultone (1.34 g, 0.011 mol) in acetone (12 mL) was slowly added to the flask containing the akyl imidazole (0.012 mol) at 0 C. The reaction mixture was heated to the room temperature and, then, stirred for 5 days. After that, the reaction solution was filtrated giving the product as a solid. The solid was washed two times with a mixture of 1:1 hexane/dichloromethane and driedunder vacuum, giving the zwitterionic surfactant in 51% yield. The given product was characterized by 1H-NMR in CDCl3.

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:
Article; Modenez, Iago A.; Sastre, Diego E.; Moares, Fernando C.; Marques Netto, Caterina G.C.; Molecules; vol. 23; 9; (2018);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem