Category: imidazoles-derivatives

Some common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, molecular formula is C8H12N2O, 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. SDS of cas: 714273-83-3

To a solution of compound 5 (50 g329 mmol) in EtOH (200 mL), NaBD4 (41 g, 979 mmol) was added portion wise under nitrogen. The mixture was stirred for 5 h at -20. The precipitate was removed by filtration. To the filtrate, 2 mol/L aqueous hydrochloric acid (250 ml) was added, and then filtrated. The filtrate was evaporated in vacuo, and then dissolving in water, the pH of the solution was adjusted to 8-9 using saturated potassium carbonate. The crude product was gain by filtration to get 44g compound 6 with a yield at 85%, and was used for next step without further purification. 1H NMR (500 MHz, CDCl3) delta 7.72 (s, 1H), 1.48 (s, 9H). MS (ESI): m/z = 157.22 [M + H] +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 714273-83-3, its application will become more common.

Reference:
Article; Ding, Zhongpeng; Cheng, Hejuan; Wang, Shixiao; Hou, Yingwei; Zhao, Jianchun; Guan, Huashi; Li, Wenbao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1416 – 1419;,
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Imidazole | C3H4N2 – PubChem

Reference of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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 4-iodo-1H-imidazole (2.05 g, CAS: 7 1759-89-2) and trityl chloride (4.4 g, CAS: 76-83-5) in DMF (35 mL) was added triethylamine (3.04 mL, CAS: 121-44-8) at 0 C. The reaction mixture was slowly warmed to rt and was stuffed for 48 hours. The reaction mixturewas then poured into H20 (150 mL). The solid was filtered, washed with H20 (60 mL) and dried under reduced pressure. The resulting crude material was purified by flash chromatography using silica gel (EtOAc) to give the title compound as a white solid (4.3 g, 93%). Rf= 0.50 (10% EtOAc/hexane).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, 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 33016-47-6, Recommanded Product: 33016-47-6

Under argon atmosphere, 5.6 ML (2.96 mmol, 1 equivalent) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise to a solution of 1 g (2.96 mmol) of 1-trityl-1H-imidazol-4-carbaldehyde in 10 ML of THF at 3?6C. The mixture was stirred at 0?5C for 1 hour and 25 minutes. 5.6 ML (2.96 mmol, 1 equivalent) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise at 0?3C. The mixture was stirred at 2?3C for 5 hours and 30 minutes. 5 ML of 1N hydrochloric acid was added dropwise at 20C or lower, followed by dilution with 30 ML of ethyl acetate.. Then, the layers were separated.. The organic layer was washed successively with 5 ML of 1N hydrochloric acid, 5 ML of water, 5 ML (*2) of an aqueous saturated sodium bicarbonate solution, and 5 ML (*2) of an aqueous saturated sodium chloride solution.. After washing, the organic layer was dried with anhydrous magnesium sulfate.. After concentration under reduced pressure, recrystallization with 3 ML of IPE afforded 1.16 g of the desired product (yield 92%).1H NMR (CDCl3): delta 1.22 (3H, t, J=7.1 Hz), 2.83-2.86 (2H, m), 4.13 (2H, q, J=7.1 Hz), 5.09-5.13 (1H, m), 6.78 (1H, s), 7.10-7.15 (6H, m), 7.26-7.39 (10, m).

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-Trityl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1471056; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, molecular formula is C8H12N2O2, 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. Quality Control of Ethyl 3-(1H-imidazol-2-yl)propanoate

To 3-(1H-imidazol-2-yl)propanoic acid ethyl ester [37] (68 mg, 0.40 mmol) in EtOH (0.5 mL) NaOH (2 M, 1.5 mmol, 0.75 mL) was added. The mixture was stirred for 48 h at rt before a pH-value of 1-2 with HCl (0.5 M) was adjusted. After concentration, the crude product was purified using a strong basic ion exchange resin.Colourless crystals; Yield: 61 mg (86%); mp 221 C. IR (KBr) nu cm-1: 3085, 2968, 2727, 1725, 1619, 1507, 1429, 1212, 1188; 500 MHz 1H NMR (CD3OD): delta = 3.21 (m, 2H, CH2COO), 3.30 (m, 2H, CH2CH2COO), 7.41 (s, 2H, CH[4H-Imid.], CH[5H-Imid.]); 126 MHz 13C NMR (CD3OD): delta = 23.6 (CH2CH2COO), 31.0 (CH2CH2COO), 119.0 (CH[4C-Imid.], CH[5C-Imid.]), 147.7 (C[2C-Imid.]), 173.7 (COO); MS (EI, 70 eV): m/z (%) = 140 (16) [M+], 95 (100); MS (CI, CH5+): m/z (%) = 141 (100) [M++1]; HMRS (EI) calcd. for C6H8N2O2: 140.0586; found 140.0583.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 172499-76-2, its application will become more common.

Reference:
Article; Hack, Silke; Woerlein, Babette; Hoefner, Georg; Pabel, Joerg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1483 – 1498;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 288-32-4, name is 1H-Imidazole, 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. SDS of cas: 288-32-4

To a DMF (20 mL) solution of 3-chloro-4-fluorobenzaldehyde (500 mg), potassium carbonate (1.20 g) and imidazole (275 mg) were added one by one, and the reaction solution was agitated at 80 C. overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (elution solvent:ethyl acetate?ethyl acetate_methanol=10:1), and 548 mg of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 10.0 (s, 1H), 8.09 (d, J=2.0 Hz, 1H), 7.91 (dd, J=2.0, 8.0 Hz, 1H), 7.80 (s, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.24-7.27 (m, 2H).

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

Reference:
Patent; Eisai Co., Ltd.; US2006/4013; (2006); 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1-methyl-1H-imidazole

To a flask containing 5-bromo-1-methyl-1H-imidazole (345 mg, 2.14 mmol) was added THF (8 mL) and the solution was cooled to 0 C. To this clear homogeneous solution was added isopropylmagnesium chloride-LiCl complex (1.3 M, 2.0 mL, 2.6 mmol) which resulted in a white suspension. The reaction was stirred at 0 C. for 30 min, then a THF (2 mL) solution of N-methoxy-N,2-dimethylthiazole-4-carboxamide (250 mg, 1.34 mmol, Intermediate 38, step a) was introduced and the mixture became more viscous and was allowed to warm to room temperature. After 3 hours the mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (20-40% EtOAc-DCM increasing gradient to 5% MeOH-DCM) provided the title compound as an off-white solid.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
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Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4, These common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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 3-((2-hydroxy-3-nitrobenzyl)(methyl)amino)-N,N-dimethylpropanamide (KR-400450) (3.70 mmol, 1.04 g) in methanol (125 mL), PtO2 (0.18 mmol, 0.04 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring.The reaction was then stirred under hydrogen atmosphere at ordinary pressure (15 psi) for three hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (90 mL). The filtrate was concentrated in vacuo yielding a brown oil. The oil was quickly re-dissolved in acetonitrile (175 mL) and di(imidazole-1-yl)methanimine (7.39 mmol, 1.19 g)was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (10:1 chloroform/methanol) provided a faint orange oil in a 64% yield. The product ofthe reduction (3-((3-amino-2-hydroxybenzyl)(methyl)amino)-N,N-dimethylpropanamide) is air sensitive and appropriate measures should be taken to minimize air exposure. An analytical sample of the title compound was isolated by reverse-phase HPLC utilizing a gradient from 3.0-20% acetonitrile in water.

Statistics shows that Di(1H-imidazol-1-yl)methanimine is playing an increasingly important role. we look forward to future research findings about 104619-51-4.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]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 405173-97-9, SDS of cas: 405173-97-9

The crude isoquinuclidine hydroiodide (106 mg, 0.40 mmol) , obtained by TMSI deprotection of 8 and triethylamine (0.17 mL, 121 mg, 1.2 mmol) in anhydrous DMF (1.5 mL) was stirred under argon at room temperature for 10 min. 2-(2′- chloroethyl ) benzimidazole (72 mg, 0.40 mmol) was then added to the above mixture and the resulting solution was allowed to stir at room temperature overnight. After the workup, the crude mixture was purified by RP-HPLC to afford a pale yellow oil (48 mg, 43% yield) . 1R NMR (300 MHz, CD3OD) delta 7.68 (2H, dd, J= 6.2, 3.2 Hz), 7.48 (2H, dd, J= 6.2, 3.1 Hz), 6.75 (1H, dd, J= 7.7, 7.7 Hz), 6.25 (1H, dd, J= 7.7, 7.7 Hz), 4.25 (1H, d, J= 5.2 Hz), 3.60 (3H, m) , 3.45 (2H, m) , 2.93 (1H, m) , 2.80 (1H, d, J= 10.5 Hz), 2.14 (1H, m) , 1.94 (1H, ddd, J= 12.6, 9.1, 2.9 Hz), 1.25 (1H, m) , 1.04 (1H, m) , 0.94 (1H, dddd, J= 7.9, 5.2, 2.6, 2.6 Hz), 0.85 (3H, t, J= 7.4 Hz); 13C NMR (75 MHz, CD3OD) delta 150.5, 140.4, 133.5, 133.5, 127.1, 127.1, 126.0, 115.1, 115.1, 59.9, 53.6, 53.3, 37.1, 30.8, 29.1, 28.9, 23.5, 11.3; m/z calcd for C18H23N3 281.19, found 281.73.

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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; SAMES, Dalibor; LI, Xiaoguang; LI, Shu; KRUEGEL, Andrew; KARPOWICZ, Richard; CARRERA, Ignacio; RAKSHIT, Souvik; WO2013/28999; (2013); A1;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 1467-16-9, A common heterocyclic compound, 1467-16-9, name is 1H-Imidazole hydrochloride, molecular formula is C3H5ClN2, 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.

Solutions of [H(imidazolium)][Cl] (0.048 g, 45 mmol) in 2 mL CH3CN and K2B12F12 (0.10 mg, 0.22 mmol) in 2 mL CH3CN were mixed at room temperature, affording 0.10 g of salt 3 (93% yield). Single-crystal X-ray diffraction analysis confirmed the composition of this salt.

The synthetic route of 1467-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Belletire, John L.; Schneider, Stefan; Shackelford, Scott A.; Peryshkov, Dmitry V.; Strauss, Steven H.; Journal of Fluorine Chemistry; vol. 132; 11; (2011); p. 925 – 936;,
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Imidazole | C3H4N2 – PubChem

Application of 39021-62-0, 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.

Under N2 at -78 100 mL 3-neck round bottom flask at nBuLi (hexane of 2.5 M, 0.52 mL, 1.3 mmol) to dry THF (10 mL) of 6-bromo-2,4-dichloro-3 – phenyl quinoline (353 mg, 1 mmol, intermediate 1: step c) was added dropwise to a solution of. Continuous stirring for 30 minutes, was added a solution of dry THF (10 mL) of 1-methyl -1H- imidazole-5-carbaldehyde (110 mg, 1 mmol) at -78 . The cooling bath was removed and was gradually The mixture was warmed to RT, stirred for 2 hours. The mixture was then quenched by the addition of H2O (10 mL), extracted with CH2Cl2 (2 × 50 mL). Dry the combined organic phases with Na2SO4 and concentrated to dryness, prep-TLC: Purification of (CH3OH / CH2Cl2 1 evolves to 5) to give the title compound as a white solid.

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem