Category: imidazoles-derivatives

Synthetic Route 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 3-1 (1.55 g, 4.4 mmol), benzimidazolo[1,2-a]benzimidazole (960 mg, 4.6 mmol), and potassium phosphate (1.97 g, 9.3 mmol) were suspended in NMP (22 mL). The mixture was stirred at 190 Cfor 18.5 h. After the reaction mixture was cooled at roomtemperature, 44 mL of EtCH and 22 mL of water were added to the reaction mixture to give a solid. It was collected by filtration, and it was purifed by column chromatography on silica gel eluting with a mixed solvent of toluene and CHCI3.The product was further purified by recrystallization with toluene and cyclohexane to result in compound A-1O (yield: 1.55 g (65%)) as a white solid. LC-MS (mlz) 538.1HNMR (300 MHz, DMSO-c): 68.42-8.39 (m, 2H), 8.32-8.25 (m, 2H), 7.95-7.82 (m, 3H),7.72 (dd, J= 1.2, 7.6 Hz, 1H), 7.61-7.58 (m, 1H), 7.50-7.32 (m, 9H), 7.25 (t, J= 7.9 Hz,1H), 7.20-7.17 (m, 2H), 6.38 (dd, J= 1.1, 8.0 Hz, 1H)

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

Electric Literature of 2849-93-6, 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1H-benzo[djimidazole-2-carboxylic acid (161 mg, 990 imol, 1.2 eq) in 2 mL of DMF was added HATU (377 mg, 990imol, 1.2 eq) and TEA (167 mg, 1.6 mmol, 229 tL, 2.0 eq). The mixture was stirred at 15 Cfor 0.5 hour, then tert-butyl N-[(1R,3S)-3-(ethylamino)cyclohexylj carbamate, compound 2,(200 mg, 825 imol, 1.0 eq) was added and the resulting reaction mixture was stirred at 15 Cfor additional 15.5 hours. The reaction mixture was partitioned between 5 mL of water and 5 mL of ethyl acetate. The organic phase was separated, washed twice with 10 mL of brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give an oil. The oil was purified by prep-TLC (Si02, eluting with petroleum ether: ethyl acetate = 1:1) to give 150mg of compound 65 (388 imol, 47% yield) as a colorless gum.

The synthetic route of 1H-Benzimidazole-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17325-26-7, These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-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.

To a solution of 5-fluoro-indan-1-ol (0.293 g, 1.925 mmol) and methyl 4- imidazolecarboxylate (CASNo. 17325-26-7, 0.163 g, 1.290 mmol) in.THF (10 mL) at 0 0C is added pMe2NPhP(Ph)2 (0.619 g, 1.925 mmol) and diisopropyl azodicarboxylate (94%, 0.414 g, 1.925 mmol). After 1 hour the mixture is warmed to room temperature and after 18 hours it is diluted with ethyl acetate and extracted with 1M aqueous HCI. The extracts are cooled to 0 0C, and the pH is adjusted to ca. 9 with ice-cold 4M aqueous NaOH. The basic aqueous phase is extracted three times with dichloromethane, and the combined organic phases are dried over magnesium sulfate, filtered through a cotton plug, and concentrated. The resulting residue is purified by silica gel flash chromatography (elution with dichloromethane- methanol, 1 :0 to 99:1 to 49:1) to afford 3-(5-fluoro-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 261.0 (M+H) The HCI salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1 N HCI in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCI salt of 3-(5-fluoro-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; 1H NMR (400 MHz1 CDCI3) delta ppm 2.06 – 2.20 (m, 1 H), 2.71 – 2.85 (m, 1 H), 2.87 – 3.00 (m, 1 H), 3.00 – 3.14 (m, 1 H), 3.87 (s, 3 H)1 6.47 (dd, J=7.7, 4.7 Hz, 1 H), 6.88 – 6.97 (m, 1 H), 7.01 (dd, J=8.6, 2.3 Hz1 1 H), 7.16 (dd, J=8.6, 5.1 Hz, 1 H), 7.19 (s, 1 H)1 7.77 (s, 1 H).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33543-78-1, The chemical industry reduces the impact on the environment during synthesis 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, I believe this compound will play a more active role in future production and life.

a solution of 3.65 g of 1,8-diazabicyclo[5.4.0]undec-7-ene in 10 ml of chloroform is added dropwise over 20 minutes at a temperature close to 20¡ã C. to a solution of 2.8 g of ethyl imidazole-2-carboxylate and 6.1 g of 2-bromo-5-chloro-1-indanone. After stirring for 2 hours and adding 100 ml of distilled water, the mixture is extracted 3 times with a total of 75 ml of chloroform and the organic extracts are pooled, dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 50¡ã C. After silica gel chromatography with a dichloromethane-ethyl acetate mixture (70-30 by volume), 1 g of ethyl 1-(5-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate is obtained in the form of a thick yellow oil Rf=0.3, thin-layer chromatography on silica gel; solvent: dichloromethane-ethyl acetate (70-30 by[volume)]. The 2-bromo-5-chloro-1-indanone can be prepared as described in German Patent 2,640,358.

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, Ethyl 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (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. 15469-97-3, name is 1-Trityl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C22H18N2

EXAMPLE 54 STR84 Preparation of (+-)-trans-4-(2-(4-cyclopentylbut-1-ynyl)cyclopropyl)imidazole (54). (+-)-trans-4-(2-(4-Cyclopentylbut-1-ynyl)cyclopropyl)imidazole was prepared as described for the Example 38 except racemic mixture of 4-(2-ethylnylcyclopropyl)-1-(triphenylmethyl)imidazole was used. (+-)-trans-4-(2-(4-Cyclopentylbut-1-ynyl)cyclopropyl)imidazole (54). 1 H-NMR (300 MHz, CD3 OD): delta 7.51 (s, 1H), 6.81 (s, 1H), 2.14 (m, 2H), 2.04 (m, 1H), 1.88 (m, 1H), 1.80 (m, 2H), 1.65-1.39 (m, 7H), 1.17-1.02 (m, 4H); MS (Cl) m/e 229(M+1).

The synthetic route of 15469-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gliatech, Inc.; US6008240; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 312-73-2, A common heterocyclic compound, 312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H5F3N2, 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.

Compound II (60.00g, 0.322mol, 1.0eq.) And cesium carbonate (159.98g, 0.483mol, 1.5eq.) Were added to 600mL DMF, and ethyl iodide (75.33g, 0.483mol, 1.5) was added dropwise at 0 C. eq.), the reaction was completed at 25 C for 1h after the addition, TLC showed that the raw materials had reacted, the system was poured into 1L of ice water, washed with water (100mL * 2), filtered to obtain a white solid, washed with water (100mL * 2), white The solid was dissolved with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to obtain compound III-2 as a white solid 61.01g, yield: 88.5%.

The synthetic route of 312-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Yaoshi Technology Co., Ltd.; Wang Zhengjiang; Xia Aihua; (15 pag.)CN110903245; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 86604-86-6, A common heterocyclic compound, 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, molecular formula is C8H4ClF3N2, 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 2 N-(5-(Trifluoromethyl)-1H-benzo[d]imidazol-2-yl)quinolin-8-amine A mixture of 2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole (66 mg, 0.3 mol, prepared according to the procedure described in WO 2004/035549 A1) and 8-aminoquinoline (29 mg, 0.6 mmol, Aldrich) in EtOH (2 mL) was subjected to microwave irradiation at 170 C. with stirring for 30 min. The reaction mixture was allowed to cool to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel chromatography eluding with 3% MeOH/DCM to give the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 329 (M+1).

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; Norman, Mark H.; Ognyanov, Vassil I.; Wang, Xianghong; US2006/160872; (2006); 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. 13750-62-4, name is 1-Benzyl-2-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 13750-62-4

General procedure: A 16 mL vial with a PTFE/silicone septum and a nitrogen-bubbler line was charged with N-benzylbenzimidazole (208.1 mg, 1.0 mmol), Pd/C (10 wt %, dry powder, reduced) (20 mg) and THF (5 mL). The mixture was treated at rt with triethylsilane (320 muL, 2.0 mmol) and then stirred under nitrogen for 14 h at rt. The mixture was filtered through a 0.45 muM PTFE syringe filter and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (0 to 10% MeOH/ dichloromethane) to afford benzimidazole as a colorless solid (117.6 mg, 0.996 mmol 99%). The reactions generally exhibit an induction period of 5 to 30 min as indicated by the initiation of gas release (i.e., bubbling) from the reaction mixture. The use of Pd/C on a dry matrix is imperative as wet Pd/C results in decreased yield or no reaction.

The synthetic route of 13750-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Graham, Thomas H.; Tetrahedron Letters; vol. 56; 21; (2015); p. 2688 – 2690;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-91-4, These common heterocyclic compound, 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, 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 stirred suspension of NaH (68 mg, 1.71 mmol, 60% in mineral oil) in dry THF (5 mL) at 0 C was added a dry THF (6 mL) solution of 54 (268 mg, 1.14 mmol). After 30 min of stirring at 0 C, 2,4,5-tribromo-1-methyl-1H-imidazole [38] (399 mg, 1.10 mmol) was added. The reaction mixture was refluxed overnight, then cooled, and poured into ice water (?10 mL). The resulting mixture was extracted with EtOAc (2 * 10 mL). The combined organic phases were extracted with aq HCl solution (1M, 2 * 6 mL). The combined water phases were basified to pH 14 with a concentrated aq NaOH solution and extracted with EtOAc (3 * 10 mL). The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo. Purification by DCVC (DCM:MeOH:NH3/100:0:0 to 100:13:1) gave 1-((4,5-dibromo-1-methyl-1H-imidazol-2-yl)oxy-N,N-dimethyl-7-phenylheptan-3-amine as a yellow oil (155 mg, 29%). 1H NMR (CD3OD, 400 MHz) delta 7.26-7.20 (m, 3H), 7.18-7.10 (m, 3H), 4.41-4.29 (m, 2H), 3.36 (s, 3H), 2.62 (t, 3H, J = 7.5 Hz), 2.33 (s, 6H), 2.00 (dq, 1H, J = 14.4, 7.8 Hz), 1.81 (dq, 1H, J = 7.8, 6.8 Hz), 1.69-1.61 (m, 4H), 1.39-1.37 (m, 2H). 13C NMR (CD3OD, 101 MHz) delta 129.55 (2C), 129.44 (2C), 126.85, 110.88, 69.83, 62.27, 40.79 (2C), 36.88, 32.82, 31.03, 30.32, 27.78.

Statistics shows that 2,4,5-Tribromo-1-methylimidazole is playing an increasingly important role. we look forward to future research findings about 1003-91-4.

Reference:
Article; Bach, Tinna B.; Jensen, Anders A.; Petersen, Jette G.; S¡ãrensen, Troels E.; Della Volpe, Serena; Liu, Jun; Blaazer, Antoni R.; Van Muijlwijk-Koezen, Jacqueline E.; Balle, Thomas; Fr¡ãlund, Bente; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 425 – 444;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 641571-11-1, category: imidazoles-derivatives

To a solution of 13 (100 mg, 0.33 mmol) in NMP (2 mL) was added SOd2 (58 mg, 0.49 mmol). The reaction was heated at 90 C for 1 hour before 3 (80 mg, 0.33 mmol) was added. The resulting mixture was stirred at 90 C for 3 hours. The reaction was quenched with water and basified with aqueous NaOH. The mixture was extracted with EtOAc twice. The combined organic layers were washed with brine, dried overNa2SO4 and concentrated. The residue was purified by reverse prep-HPLC and then silica gel prep-TLC to give 4-methyl-N-(3-(4-methyl-1 H-imidazol-1 -yl)-5- (trifluoromethyl)phenyl)-3-((4-phenylpyrimidin-2-yl)amino)benzamide (22 mg, 13%) as a white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem