Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, 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 19225-92-4, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-imidazole

[1-[3-(1-Methyl-1H-imidazol-2-ylmethoxymethyl)-phenyl]-1 H-imidazole-4- carboxylic acid ethyl ester] (14a)To a suspension of NaH (308 mg, 7.7 mmol, 60% in mineral oil) in dry THF (6 ml_) under N2 atmosphere was added a solution of alcohol 7 (410 mg, 1.38 mmol) in THF (2 ml_) while stirring for 30 min at room temperature. The reaction mixture was cooled to O0C and the compound 14 (crude 200 mg, 1.53 mmol) in THF (1 ml_) was added dropwise and allowed to come to room temperature during a period of 30 min after which it was refluxed for 12 h. The mixture was quenched with ice water (5 ml_), acidified to pH 2-3 by adding aqueous HCI solution (2N). The reaction mixture was extracted with CH2CI2 (3 x 20 ml_), washed with brine, dried over Na2SO4 and concentrated. The crude mass was taken in ethanol (10 ml_), purged HCI gas for 30 min. and stirred at room temperature for 3 h. After evaporation of solvent, the crude mass was purified by column chromatography using 28% ethylacetate in hexane to furnish 14a (150 mg, 25%) as a white solid, mp-83.8-88.6C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Chloromethyl)-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; NEUROSEARCH A/S; WO2007/42545; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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 14741-71-0, Quality Control of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

General procedure: To the dry solid of compound 3 (2.04 g, 0.01 mol) ammonium acetate (0.50 g) eithercyclophentanone (0.78 g, 0.01 mol) or cyclohexanone (0.92 g, 0.01 mol) were added. Thereaction mixture was heated in an oil bath at 120 oC for 1 h then left to cool. The product wastriturated with ethanol and the formed solid product was collected by filtration

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, and friends who are interested can also refer to it.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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 492-98-8, Formula: C6H6N4

General procedure: 2,2′-Biimidazole (0.4 g, 3 mmol) was added to a 100mLthree-necked flask charged with 3-chloropropionic acid (1.3 g,12 mmol), KOH (0.336 g, 6 mmol), and water (10 mL) at roomtemperature. The reaction mixture was adjusted to a pH level of10 to 12 with a 5M aqueous solution of KOH and the reactionmixture was heated slowly to reflux for 8 h. The product mixturewas acidified to pH2-3 with hydrochloric acid (1 M), and thenconcentrated under reduced pressure. The concentrated mixturewas diluted with ethanol and filtered to remove the undissolvedsalt. The final filtrate was concentrated to give a brown viscousliquid (85.1% yield). The product was dried overnight undervacuum before use and analysis.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H,1’H-2,2′-Biimidazole, and friends who are interested can also refer to it.

Reference:
Article; Feng, Miaona; Zhao, Guoying; Gao, Hongling; Zhang, Suojiang; Australian Journal of Chemistry; vol. 68; 10; (2015); p. 1513 – 1517;,
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. Formula: C5H6N2O

3-Methyl-3H-imidazole-4- carbaldehyde (10) (4.0 g, 15 mmol) was suspended in THF (10 mL), and the resulting solution cooled to 0C. Lithium aluminum hydride (300 mg, 32.0 mmol) was added portion wise over 10 minutes, and the resulting suspension stirred for a further 10 minutes. Excess hydride was quenched by the addition of solid Na2SO4-IOH2O (~1 g) in large portions with vigorous stirring. Additional THF was added as needed to prevent solidification of the resulting slurry. The resulting suspension was stirred for a further hour, and then filtered to remove the sulfate salts, and the solvent was removed under reduced pressure to provide the title alcohol (1.3 g, 80%). 1H NMR (400 MHz, ^-MeOH): delta 7.57 (s, IH), 6.89 (s, IH), 4.58 (s, 2H), 372 (s, 3H). 13C NMR (100 MHz, ^-MeOH): delta 140.1, 132.7, 128.1, 31.9, 31.0.

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

Reference:
Patent; YALE UNIVERSITY; UNIVERSITY OF SOUTH FLORIDA; UNIVERSITY OF WASHINGTON; SEBTI, Said; WO2006/102159; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10597-52-1, 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. 10597-52-1 name is 7-Nitro-1H-benzo[d]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.

Step B: Preparation of tert-butyl 4-nitro-1H-benzo[d]imidazole-1-carboxylate: Triethylamine (1.03 mL, 7.36 mmol) was added to a suspension of 4-nitro-1H-benzo[d]imidazole (1.0 g, 6.13 mmol) in dichloromethane (50 mL), followed by addition of Boc2O (1.61 g, 7.36 mmol). The reaction was stirred at room temperature for 16 hours and then quenched with water (20 mL). The aqueous layer was extracted with dichloromethane (50 mL*3), and the combined organics were dried, filtered and concentrated. The crude product was purified by flash column chromatography, eluding with hexanes/ethyl acetate (4:1) to give the desired product (1.50 g, 93%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Nitro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); 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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H3BrN2

Intermediate E-0 (13.6 g) was dissolved in 80 mL of NMP and compound 275-4 (6.5 g) and Na2C03 (4.6 g) were added. The solution was stirred at 90 C for 6 h, then NMP was removed under reduced pressure. The residue was dissolved in EtOAc, washed with water and purified by silica gel flash chromatography (PE: EA= 2: 1) to give compound 275-5 as a yellow oil.

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; ELAN PHARMACEUTICALS, INC.; NEITZ, R., Jeffrey; TROUNG, Anh, P.; GALEMMO, Robert, A.; YE, Xiaocong, Michael; SEALY, Jennifer; ADLER, Marc; BOWERS, Simeon; BEROZA, Paul; ANDERSON, John, P.; AUBELE, Danielle, L.; ARTIS, Dean, Richard; HOM, Roy, K.; ZHU, Yong-liang; WO2012/48129; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, 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 17228-38-5, name: N-Methyl-1H-benzo[d]imidazol-2-amine

(5R,8aS)-3-Chloro-1 -(1 -methanesulfonyl-1 -methyl-ethyl)-5-methyl-5,6,8a,9- tetrahydro-8H-7,1 0-dioxa-2,4,4b-triaza-phenanthrene (1 .85 g), benzimidazole2-yl-methylamine (719 mg), tris(dibenzylideneacetone)dipalladium(0) (895 mg; 0.2 eq.) and dicyclohexyl-(2?,4?,6?-triisopropyl-biphenyl-2-yl)-phosphane (932 mg) were dissolved in dioxane (10 ml), lithium tert-butoxide (1,0 M solution in tetrahydrofuran) (6.8 ml, 1.4 eq) was added and the mixture was stirred for 1 h at 80 00. The reaction mixture was purified by chromatography(dichloromethane I methanol) to afford {1 -[(5R,8aS)-1 -(1 -Methanesulfonyl-1 -methyl-ethyl )-5-methyl -5,6 ,8a ,9-tetrahyd ro-8 H-7, 1 0-d ioxa-2 ,4 ,4b-triaza-phenanthren-3-yl]-1 H-benzimidazol-2-yl}-methyl-amine as a yellow solid (1 .18g); LCMS (method E): 0.50 mm (purity 98%); [MH+] 473.3 mlz; 1H NMR (500MHz, DMSO-d6) 6 8.19 (q, J = 4.8 Hz, 1 H), 8.00 (d, J = 7.6 Hz, 1 H), 7.28 -7.21 (m, 1 H), 7.07 (td, J = 7.6, 1 .2 Hz, 1 H), 6.97 (td, J = 7.7, 1 .3 Hz, 1 H), 4.63 (qd, J = 6.8, 2.9 Hz, 1 H), 4.43 (dd, J = 11 .0, 3.4 Hz, 1 H), 4.04 – 3.94 (m, 2H),3.88 (d, J= 11.6 Hz, 1H), 3.83 (dd, J= 11.1,9.2Hz, 1H), 3.70 (dd, J 11.6,3.2 Hz, 1 H), 3.22 -3.15 (m, 1 H), 3.05-3.01 (m, 6H), 1.84 (5, 3H), 1.81(s, 3H), 1 .35 (d, J = 6.8 Hz, 3H)and (1 H-Benzimidazol-2-yl)-[(5R,8aS)-1 -(1 -methanesulfonyl-1 -methyl-ethyl)-5- methyl-5,6,8a,9-tetrahydro-8H-7, 1 0-dioxa-2,4,4b-triaza-phenanthren-3-yl]-methyl-amine as a beige solid (722 mg); LCMS (method E): 0.53 mm (purity94%);[MH+]473.3m/z; 1H NMR (400 MHz, DMSO-d6)o 12.40(s, 1H),7.45-7.38 (m, 1 H), 7.34 – 7.27 (m, 1 H), 7.11 – 7.00 (m, 2H), 4.67 (qd, J = 6.5, 2.7Hz, 1 H), 4.38 (dd, J = 11 .0, 3.5 Hz, 1 H), 3.99 – 3.89 (m, 2H), 3.82 (d, J = 11.5Hz, 1 H), 3.76 (dd, J = 11 .0, 8.8 Hz, 1 H), 3.72 (s, 3H), 3.65 (dd, J = 11.7, 3.3 Hz, 1H), 3.15 (t, J= 11.8 Hz, 1H), 3.04 (s, 3H), 1.83 (s, 3H), 1.81 (s, 3H), 1.29(d, J = 6.8 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Methyl-1H-benzo[d]imidazol-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; BURGDORF, Lars; DORSCH, Dieter; TSAKLAKIDIS, Christos; (189 pag.)WO2017/202748; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-13-3, These common heterocyclic compound, 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, 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.

Example 17; N- 3 -(2, 5 ‘-Bipyrimidin-4-ylamino”)-4-methylphenyll -3 -(4-methy 1- 1 iZ-imidazol- 1 -vD-5- (trifluoromethyDbenzamide; A solution of 3 -(4-methy 1- 1 H-imidazol- 1 -y l)-5 -(trifluoromethyl)benzoic acid (Method27; 100 mg5 0.36 mmol), N3-255’-bipyrimidin-4-yl-4-methylbenzene-l53-diamine (Method 20; 97 mg5 0.36 mmol) and DIEA (0.25 ml, 1.08 mmol) in DMF (5 ml) was treated with HATU (205 mg, 0.40 mmol). The reaction mixture was stirred for 15 h at 25 C. The reaction was quenched with 10% NaOH and extracted with EtOAc. The organics were dried with NaCl(sat) and then Na2SO4(S) and removed under reduced pressure. The residue was purified by reverse phase semi-preparative chromatography to give the title compound. NMR (300 MHz): 10.75 (s, IH)5 9.75 (s, IH), 9.45 (s, 2H)5 9.41 (s, IH), 9.21 (s, IH)5 8.66 (s, IH), 8.33 – 8.45 (m, 3H), 8.17 – 8.22 (m, 2H), 7.52 (d, IH), 7.27 (d, IH)5 6.73 (d, IH)5 2.31 (s, 3H)5 2.19 (s, 3H); m/z 531.

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid is playing an increasingly important role. we look forward to future research findings about 641571-13-3.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/79791; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10597-52-1, A common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, 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.

4-Nitro-1-(3-nitrophenyl)benzimidazole was prepared analogueously to 3 g from 4-nitrobenzimidazole and 1-fluoro-3-nitrobenzene. Mp 260-262 C. 1-(3-Aminophenyl)-4-nitrobenzimidazole was prepared from 4-nitro-1-(3-nitrophenyl)benzimidazole as described in Example 3a. Mp 159-161 C.

The synthetic route of 10597-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NeuroSearch A/S; Meiji Seika Kaisha, Ltd.; US5554630; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1243204-92-3, A common heterocyclic compound, 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, molecular formula is C12H11N3O, 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.

b) Preparation of intermediate 2 and 2a. A stirred sol. of intermediate 1 (1.40 g, 6.57 mmol) in anhydrous EtOH (1.4 ml) and Et2O (28 ml) was cooled at 0 0C. HCl gas was bubbled through the contents for 20 min, then the ensuing r.m. left to stir overnight at r.t. The precipitated product was collected by filtration and dried to give the HCl salt of the desired product as an off-white solid. Yield: 1.72 g of intermediate 2 (78.9%). Intermediate 2 was used as such in the next reaction step, or was converted into the free base by dissolving it in water, basifying the solution via addition of Na2Ctheta3, and extraction of the resulting suspension with DCM. The organic layer was dried (MgSO4), filtered and cone, in vacuo to yield intermediate 2a (quantitative yield).

The synthetic route of 1243204-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem