Tag: M.W=100-200

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. 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Intermediate 158 Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-((1-methyl-1H-imidazol-2-yl)methoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate [0988] Methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (Intermediate 28-29) (46.3 mg) and 2-(chloromethyl)-1-methyl-1H-imidazole (39.2 mg) were suspended in dimethylformamide (1.8 mL) and potassium carbonate (62 mg) was added. The reaction mixture was shaken for 24 h at 60 C. Another portion of 2-(chloromethyl)-1-methyl-1H-imidazole (39.2 mg) and potassium carbonate (62 mg) was added and the mixture was shaken again for 24 h at 60 C. and than directly chromatographed by HPLC on reversed phase. The product fractions are collected and lyophilized to give the title compound. Yield: 31.5 mg; LC (method 23): tR=1.54 min; Mass spectrum (ESI+): m/z=557 [M+H]+.

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; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

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

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

These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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. Recommanded Product: 39021-62-0

3-Methyl-3H-imidazole-4- carbaldehyde (10) (4.0 g, 15 mmol) was suspended in THF (10 mL), and the resulting solution cooled to 0°C. 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, 80percent). 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 1-Methyl-1H-imidazole-5-carbaldehyde 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

Adding a certain compound to certain chemical reactions, such as: 13739-48-5, name is 2-Methyl-4-phenyl-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 13739-48-5, Computed Properties of C10H10N2

5.86 3-{4-[4-(2-METHYL-4-PHENYL-IMIDAZOL-1-YLMETHYL)-BENZYLOXY]-1-OXO-1,3-DIHYDRO-ISOINDOL-2-YL}-PIPERIDINE-2,6-DIONE To the stirred solution of 2-methyl-4-phenyl-1H-imidazole (157 mg, 0.99 mmol) in Acetonitrile (15 mL) was added 3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (400 mg, 0.9 mmol) and DIPEA (0.24 ml, 1.35 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 days before the reaction mixture was diluted by EtOAc (40 mL) and NaHCO3 (aq, sat., 20 mL). The mixture was extracted. Some solid was formed and the mixture was filtered. And the solid was dissolved in DCM (20 mL) and MeOH (5 mL). All organic layers were combined and dried by MgSO4 and concentrated. The residue was purified by ISCO to give 3-{4-[4-(2-Methyl-4-phenyl-imidazol-1-ylmethyl)-benzyloxy]-1-oxo-1,3-dihydro-isoindol-2-yl}-piperidine-2,6-dione as a white solid (310 mg, 66% yield). HPLC: Waters Symmetry C-18, 3.9*150 mm, 5 mum, 1 mL/min, 240 nm, 25/75, (CH3CN/0.1% H3PO4), 5.26 min (99.6%); mp: 270-272 C.; 1H NMR (DMSO-d6) delta 1.91-2.03 (m, 1H, CHH), 2.30 (s, 3H, CH3), 2.43 (dd, J=4.3, 13.0 Hz, 1H, CHH), 2.53-2.63 (m, 1H, CHH), 2.82-2.97 (m, 1H, CHH), 4.23 (d, J=17.6 Hz, 1H, CHH), 4.39 (d, J=17.6 Hz, 1H, CHH), 5.04-5.16 (m, 1H, CHH), 5.18 (s, 2H, CH2), 5.23 (s, 2H, CH2), 7.10-7.20 (m, 1H, Ar), 7.20-7.26 (m, J=8.1 Hz, 2H, Ar), 7.26-7.36 (m, 4H, Ar), 7.42-7.54 (m, 314, Ar), 7.62 (s, 1H, NH), 7.64-7.75 (m, 2H, Ar), 10.96 (s, 1H, NH); 13C NMR (DMSO-d6) delta 12.76, 22.31, 31.16, 45.04, 48.59, 51.55, 69.17, 114.93, 115.25, 116.49, 123.92, 125.88, 127.15, 128.14, 128.36, 129.78, 129.95, 133.30, 134.58, 135.98, 137.15, 138.50, 144.57, 153.39, 167.97, 170.93, 172.80; LCMS MH=521; Anal. Calcd for C31H28N4O4+0.3 H2O: C, 70.79; H, 5.48; N, 10.65; Found: C, 70.68; H, 5.21; N, 10.52. The regio isomeric structure was confirmed by ROESY.

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; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem