Category: imidazoles-derivatives

Synthetic Route of 17325-26-7, 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 17325-26-7 as follows.

To a mixture of methyl 1H-imidazole-4-carboxylate (2.0 g, 15.9 mmol) in DMF (30 mL), were added DIPEA (4.1 g, 31.72 mmol), then SEM-Cl (4.0 g, 23.4 mmol) dropwise. The reaction mixture was stirred at RT for 16 h, then quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography over silica gel (EtOAc in PE 30~50%, v/v) to give methyl 1-((2- (trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate as a colorless oil (2.13 g, 52%). LC-MS (ESI): m/z (M+1)+ = 257.21.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REMEDY PLAN, INC.; CRIMMINS, Gregory, Thomas; DE JESUS DIAZ, Dennise, Alexandra; BHURRUTH-ALCOR, Yushma; (483 pag.)WO2019/213570; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, 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 1402838-08-7, category: imidazoles-derivatives

1-(2-Hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)ethyl-1-one (100 mg, 0.46 mmol),2-(1-Triphenylmethyl-1H-imidazol-4-yl)benzaldehyde (190 mg, 0.46 mmol) was dissolved in tetrahydrofuran (4.0 mL).The sodium ethoxide solution (31 mg, 21%/wt%) was added dropwise and stirred at room temperature overnight.After TLC monitoring, the reaction was completed, the solvent was evaporated under reduced pressure, and saturated ammonium chloride solution (10 mL) was added.Extracted with dichloromethane (20 mL), and the organic phase was evaporated to dryness.The residue was used directly in the next step.The residue obtained above was dissolved in a mixed solution of methanol (4 mL) and acetic acid (1 mL).After reacting at 90 C for 3 h, TLC detected the reaction completely.The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography.Obtained the target Compound114mg,The yield was 72%.

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, 2-(1-Trityl-4-imidazolyl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Suzhou Guokuang Pharmaceutical Technology Co., Ltd.; Hangzhou Anuo Bio-pharmaceutical Technology Co., Ltd.; Mei Desheng; Lu Yang; Yang Donghui; Li Pan; (50 pag.)CN108424415; (2018); A;,
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 641571-13-3 as follows. Computed Properties of C12H9F3N2O2

3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid (10 mg, 0.030 mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (22 mg, 0.058 mmol), and TEA (7.9 mg, 0.078 mmol) were dissolved in DMF (0.2 ml), the solution was stirred at 45 C. for 30 minutes, and then the compound F (10 mg, 0.030 mmol) was added, followed by stirring the solution at 45 C. for 12 hours. After the reaction was completed, ethyl acetate was added, and the reaction mixture was washed with a saturated aqueous NaCl solution. The organic layer was dried with sodium sulfate anhydrous and filtered, and then the solvent was removed under reduced pressure. The residue was crystallized to obtain a target compound 3-(4-methyl-1H-imidazol-1-yl)-N-(4-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)-5-(trifluoromethyl)benzamide (10.3 mg, 67%). 1H NMR (400 MHz, DMSO-d6) delta 10.77 (1H, s), 10.53 (1H, s), 8.49 (1H, s), 8.43 (1H, s), 8.27 (1H, s), 8.19 (1H, s), 8.09 (2H, d, J=8.8 Hz), 7.95 (2H, d, J=8.8 Hz), 7.75 (1H, s), 7.52 (1H, d, J=4.0 Hz), 7.02 (1H, d, J=3.6 Hz), 3.61 (2H, s), 2.19 (3H, s) (Exact mass 509.11, m/z 510.1193)

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Industry-University Cooperation Foundation Hanyang University ERICA Campus; HAH, Jung-Mi; LEE, Jung Hun; KIM, Minjung; (30 pag.)US2018/37589; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 20075-26-7,Some common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, 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.

A. Preparation of alpha-(2,4-dichlorophenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol This compound was prepared by the procedure described in Example XXVII B, using the following materials: 9.8 g (0.088 mol) of 1-(methoxymethyl)imidazole, 10.4 g (0.09 mol) of N,N,N’,N’-tetramethylethylenediamine, 100 ml. of anhydrous tetrahydrofuran, 62 ml. (0.10 mol) of 15% butyl lithium in n-hexane, 22.6 g (0.09 mol) of 2,4-dichlorobenzophenone in 100 ml. of anhydrous tetrahydrofuran. The reaction mixture was decomposed with 75 ml. of water. The solid matter formed was filtered off and the aqueous phase of the filtrate was discarded. The organic phase was concentrated. The residue appeared to be identical to the solid matter filtered off. The combined solid substances were crystallized from isopropyl alcohol. alpha-(2,4-Dichlorophenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol was obtained. Melting point 161-161.5 C.

The synthetic route of 20075-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gist-Brocades N.V.; US4152441; (1979); 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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., Application In Synthesis of Imidazole-2-carboxaldehyde

To a solution of 4-fluoronitrobenzene (7.87 g) and 2-imidazole-carboxaldehyde (5.90 g) in DMF (60 mL) was added K2CO3 (9.26 g). The mixture was heated at 80 C. under N2 for 16 h. The mixture was poured into water, and the precipitate was filtered to give 6.70 g of yellow solid. The filtrate was then extracted with EtOAc, and the organic layer was washed brine, dried over MgSO4, and concentrated to a yellow solid (5.40 g). Both batch were identified as the 4-[(2′-carboxaldehyde)imidazol-1′-yl]nitrobenzene. ESI mass spectrum z (rel. intensity) 218 (M+H, 100).

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; DuPont Pharmaceuticals Company; US6339099; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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. SDS of cas: 41716-18-1

To a stirred solution of 11-3 (0.23g, 0.4mMol), HOBT (0.06g, 0.45mMol), and 1- methyl-lH-imidazole-4-carboxylic acid (0.06g, 0.45mMol) in anhydrous DMF (2mL) was added DIEA (0.13mL, 0.8mMol) followed by EDC (0.09g, 0.5mMol). The solution was heated in the microwave reactor for 15 minutes at 800C. Solution was then treated with 0.2mL of acetic acid and was heated to 800C in the microwave reactor for 20 minutes. Upon cooling to room temperature, the solution was passed through a syringe filter and purified on a C18 reverse phase HPLC to give 12-1 as a solid. Mass (M+l) calculated: 632.2742 observed: 632.274 EPO

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of I H-imidazole-4-carboxylic acid methyl ester (83.1 mg, 0.646 mmol) in anhydrous DMF (3 mL) was added sodium hydride (60% oil suspension, 28.4 mg, 0.71 mmol). The reaction mixture was stirred at ambient temperature for one hour, and then 6-[1-(6-chloro-[1 ,2,4]triazolo[4,3-b]pyridazin-3- yl)-ethyl]-quinoline (200.0 mg, 0.646 mmol) was added. The reaction was heated in an 850C oil bath under nitrogen for overnight. LC-MS showed the reaction was not complete, and additional portions of sodium hydride (14.2 mg, 0.35 mmol) and 1 H-imidazole-4-carboxylic acid methyl ester (41.5 mg, 0.323 mmol) were added. The reaction was continued for another 2 hours at 850C under nitrogen. After cooling, the reaction was quenched with an addition of saturated aqueous ammonium chloride solution, and a lot of precipitate was observed. The solid was filtered, washed with water, methanol and ether to provide 1 -[3-(1 -quinolin-6-yl-ethyl)-[1 ,2,4]triazolo[4,3-b]pyridazin-6-yl]-1 H-imidazole-4-carboxylic acid methyl ester (164.9 mg, 64% yield).

The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/138472; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 6775-40-2,Some common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, molecular formula is C9H9N3, 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.

dissolving 2-amino-4-phenyl-1H-imidazole and iodobenzene in anhydrous t-butanol,Reaction at 80 C for 16h under the action of a catalytic system, cooled to 50 C,The reaction solvent was drained under vacuum, and extracted with dichloromethane several times, and centrifuged.A green dichloromethane extract is obtained. After the extraction is complete, the extract is collected.And dried under vacuum to obtain a crude product, which was recrystallized from a toluene / n-hexane mixed solution,Light green crystal product1,4-diphenyl-1H-imidazol-2-amine,Yield 61%,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Phenyl-1H-imidazol-2-amine, its application will become more common.

Reference:
Patent; Donghua University; Cai Zhengguo; Li Yanqing; Xiao Ru; (35 pag.)CN110396116; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 614-97-1,Some common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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-methyl-1H-benzo[d]imidazole (2.0 g, 15.13 mmol), triethylamine (5.27 mL, 37.8 mmol) in dichloromethane (30 mL) was added di-tert-butyl dicarbonate (5.27 mL, 22.70 mmol). The reaction mixture was stirred overnight at room temperature, and the resulting solution was diluted with water (30 mL), extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried, filtered, and concentrated under vacuum to afford a mixture of tert-butyl 5-methyl- 1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-methyl-1H-benzo[d]imidazole-1- carboxylate (3.12 g) as a yellow oil. LCMS m/z = 177.1 [M+H-isobutylene]+. To a solution of a mixture of tert-Butyl 5-methyl-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6- methyl-1H-benzo[d]imidazole-1-carboxylate(1.0 g, 4.31 mmol) and NBS (0.766 g, 4.31 mmol) in CCl4 (30 mL) stirred under nitrogen at room temperature was added AIBN (0.071 g, 0.431 mmol). The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature, washed with water (3 x 50 mL), and concentrated to afford a mixture of tert-butyl 5-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6- (bromomethyl)-1H-benzo[d]imidazole-1-carboxylate (0.7 g) as a yellow oil. LCMS m/z = 211.0 [M+H-boc]+. To a solution of 4-ethyl-2-mercapto-6-(4-methyl-1,4-diazepan-1-yl)pyridine-3,5- dicarbonitrile (synthesis described in example 69 step 1, 581 mg, 1.93 mmol) and triethylamine (488 mg, 4.82 mmol) in DMF (20 mL) was added a mixture of tert-butyl 5- (bromomethyl)-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-(bromomethyl)-1H- benzo[d]imidazole-1-carboxylate (600 mg, 1.93 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into 20 mL of water. The resulting solution was extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, washed with brine and water, then dried and concentrated. The residue was purified by silica gel column (0-50% ethyl acetate in hexane) to afford a mixture of tert-butyl 5-(((3,5- dicyano-4-ethyl-6-(4-methyl-1,4-diazepan-1-yl)pyridin-2-yl)thio)methyl)-1H- benzo[d]imidazole-1-carboxylate and tert-butyl 6-(((3,5-dicyano-4-ethyl-6-(4-methyl-1,4- diazepan-1-yl)pyridin-2-yl)thio)methyl)-1H-benzo[d]imidazole-1-carboxylate (410 mg, 0.77 mmol) as a yellow solid. LCMS m/z = 532.1 [M+H]+. To a mixture of tert-butyl 5-(((3,5- , pan-1-yl)pyridin-2- yl)thio)methyl)-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-(((3,5-dicyano-4-ethyl- 6-(4-methyl-1,4-diazepan-1-yl)pyridin-2-yl)thio)methyl)-1H-benzo[d]imidazole-1- carboxylate (430 mg, 0.81 mmol) in DCM (5.0 mL) was added trifluoroacetic acid (5.0 mL), then the reaction mixture was stirred overnight at room temperature. The residue was diluted with water, then adjusted to pH 13 with Na2CO3. The resulting solution was extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried and concentrated under vacuum. The residue was purified by silica gel column (50% ethyl acetate n hexane) to afford 2-(((1H- benzo[d]imidazol-5-yl)methyl)thio)-4-ethyl-6-(4-methyl-1,4-diazepan-1-yl)pyridine-3,5- dicarbonitrile (310 mg, 0.71 mmol) as a yellow oil. LCMS m/z = 432.1 [M+H]+.1H NMR (400 MHz, MeOD) delta ppm 8.18 (s, 1H), 7.67 (s, 1H), 7.59 (d, J = 8.3 Hz, 1H), 7.34 (d, J = 8.3 Hz, 1H), 4.65 (s, 2H), 3.97 (d, J = 4.8 Hz, 4H), 2.95- 2.86 (m, 2H), 2.71- 2.63 (m, 2H), 2.62- 2.56 (m, 2H), 2.28 (s, 3H), 2.09-1.99 (m, 2H), 1.32 (t, J = 6.1 Hz, 3H).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 53710-78-4, 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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 60% NaH (9.6mg, 0.24mmol) was added to a solution of 5a (100mg, 0.24mmol) in dry DMF (10mL) at room temperature. After stirring for 30min, 1-(3-chloropropyl)-1H-imidazole (52mg, 0.36mmol) was added and the mixture was then stirred for 5h at 80C. After cooling, the mixture was poured into cold water (200mL) and extracted with EtOAc (3×50mL). The combined organic phase was washed with brine (3×150mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using dichloromethane/methanol/triethylamine (120:4:1, v/v/v) as eluent to afford 64.4mg (51.0%) 6a as a red solid.

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, 1-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiaoqi; Hu, Yuanyuan; Gao, Anhui; Xu, Meng; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Li, Jia; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 589 – 603;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem