Category: imidazoles-derivatives

Electric Literature of 3012-80-4, 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

The synthetic route of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
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. 3034-62-6, name is 2-Iodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H3IN2

To a stirred solution of 2-iodo-1H-imidazole (174 mg, 896 pmol) and cyclopropyl{4-[(2-{[6- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yI)-1 H-benzimidazol-2-yI]amino}pyridin-4-yl)methyl]piperazin-1-yl}methanone (150 mg, 299 jjmol) in dioxane (2.0 mL) and water (0.5 mL) was added sodium carbonate (130 mg, 1.22 mmol) and Pd(dppf)C12 . CHCI (48.8 mg, 59.7 pmol) and Tetrakis(triphenylphosphin)palladium (69.0 mg, 59.7 ljmol). The mixture washeated to reflux for 36 h. Further 2-iodo-1H-imidazole (174 mg, 896 pmol) Pd(dppf)C12. CH2CI2 (48.8 mg, 59.7 jjmol) and Tetrakis(triphenylphosphin)palladium (69.0 mg, 59.7 pmol). were added and the mixture was heated to reflux for 7 h. Methanol was added, the mixture was filtered and the solvent was removed in vacuum. Silicagel chromatography gave a solid that was crystallized from ethanol to give 20.0 mg (14 % yield) of the title compound.LC-MS (Method 5): R1 = 2.17 mm; MS (ESIpos): m/z = 443 [M+H]1H-NMR (400 MHz, DMSO-d6) [ppm]: 2.490 (1.57), 2.495 (3.44), 2.500 (4.85), 2.505 (3.44),2.509 (1.55), 3.303 (16.00).

According to the analysis of related databases, 3034-62-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 693-98-1, name is 2-Methyl-1H-imidazole, molecular formula is C4H6N2, 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. COA of Formula: C4H6N2

General procedure: To a stirred solution of aryl halide (1.2mmol) and [Pd(pp3S4)(dba)] (1mol percent) in isopropanol (2.5ml) was added nitrogen/oxygen nucleophile (1mmol) followed by Cs2CO3 (2mol percent) in the atmosphere of air. The mixture was heated to 80°C and the progress of the reaction was monitored by TLC. After completion, the solvent was evaporated through rotavapour and the crude mixture was washed with dichloromethane-H2O and the organic phase was separated and dried over Na2SO4. The dichloromethane was evaporated followed by flash column purification on silica gel of the crude to obtain the pure products. The products were characterized using 1H, 13C NMR spectroscopy and GC?MS spectroscopy. The characterization data were in good agreement with those described in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 693-98-1, its application will become more common.

Reference:
Article; Majumder, Arpi; Gupta, Ragini; Mandal, Mrinmay; Babu, Madhu; Chakraborty, Debashis; Journal of Organometallic Chemistry; vol. 781; (2015); p. 23 – 34;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 84946-20-3, 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 84946-20-3 as follows.

1.2. 1-{1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-yl}-N-methyl-4-piperidinamine (method B) 8.7 g (0.05 mole) of 4-methylaminopiperidine (in the form of acetate), 13 g (0.05 mole) of 1-(4-fluorobenzyl)-2-chlorobenzimidazole and 13.8 g (0.1 mole) of potassium carbonate in 250 ml of isoamyl alcohol are brought to reflux temperature for 192 h. The mixture is cooled and evaporated to dryness. The residue is taken up with a mixture of water and ether and agitated until crystallization occurs. The compound (V) obtained in hydrate form is filtered off. The precipitate is taken up with toluene and agitated until dissolution has occurred, and the solution is dried with magnesium sulphate, filtered and evaporated. The residual oil is ground in petroleum ether. The solid product is filtered off and dried. The compound thereby obtained melts at 77-80 C.

According to the analysis of related databases, 84946-20-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Synthelabo; US4820710; (1989); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 137049-00-4, 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 137049-00-4 as follows.

Sodium hydride (33mg, 2eq) Soluble in 5mL anhydrous tetrahydrofuran, Compound Ib (190 mg, 1 eq) was added in portions with stirring. After stirring at room temperature for 30 minutes, Methylpyrazolesulfonyl chloride (157 mg, 1.3 eq) Dropped into the reaction solution, Stir at room temperature for 6 h, After the reaction is complete, Concentrate to tetrahydrofuran, Add 100mL of water, Adjust PH to nearly 7, Extracted with ethyl acetate three times, The organic layer was dried over anhydrous sodium sulfate and concentrated. The title compound 101 (219 mg, yield: 76%) was obtained.

According to the analysis of related databases, 137049-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shen Jingkang; Ding Jian; Geng Meiyu; Xiong Bing; Ai Jing; Ma Yuchi; Dai Yang; (77 pag.)CN108570052; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, 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 72-40-2, COA of Formula: C4H7ClN4O

[0161] Synthesis of 2-methyl-N-(naphthalen-2-yl)-9H-purin-6-amine.; [0162] This compound is synthesized according the scheme above and is characterized as follows: melting point: 85 0C. 1H NMR (300 MHz, DMSO-d6): d 10.45 (brs, NH, exchangeable), 8.65 (s, IH), 8.57 (s, IH), 7.91-7.99 (m, 4H), 7.46-7.56 (m, 2H), 2.71 (s, 3H); MS m/z : 276.1 (M + H+).

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; BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEM; UNIVERSITY OF WASHINGTON; WO2009/82691; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15469-97-3, name is 1-Trityl-1H-imidazole, 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. Recommanded Product: 15469-97-3

n-butyllithium (1.6M hexane solution, 6.9ml) was added dropwise to a solution of 1-tritylimidazole (3.10g) in THF (80mL) under ice-cooling in the argon atmosphere. After stirred at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52mL) was added. After stirred for 1.5 hours under ice-cooling and at room temperature for 1 hour, water was added to the reaction solution, followed by ethyl acetate. The extract was washed with water and a brine, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by subjecting to the silica column gel chromatography (eluent; ethyl acetate_hexane= 1:1) to obtain the title compound (1.402g) as a pale yellow oil. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J = 2.8Hz, 18.0Hz), 3.08 (1H, dd, J = 5.4Hz, 9.8Hz), 3.21 (1H, dd, J = 5.4Hz, 9.8Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J = 1.4Hz), 6.93 (1H, d, J = 1.4Hz), 7.0-7.4 (20H, m).

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1350792; (2003); A1;,
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, Quality Control of 2-(2-Chloroethyl)-1H-benzo[d]imidazole

Similarly, using 2-(2-chloroethyl)benzimidazole, the product is N-methyl-N’-[2-(2-(2-benzimidazolyl)ethylamino)-ethyl]thiourea.

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-(2-Chloroethyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smith Kline & French Laboratories Limited; US3950353; (1976); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 89830-98-8, 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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Potassium hydroxide (73.9 mg, 1.3 177 mmol%) and tert-butyl N-[(2R)-2-bromopropyl]carbamate (230.1mg, 0.96634 mmol) are added to a solution of 4-cyclopropyl-1H-imidazole (100 mg, 0.087849 mmol) in DMSO (2 mL) at 0 C. The mixture is stirred at room temperature for 65 hours. The reaction is quenched with water and extracted with EtOAc (3x). The organic extracts are washed with saturated NaC1 (3x), dried over Na2SO4, filtered, and concentrated to dryness. The residue is purified bysilica gel flash chromatography with 4% MeOH in DCM to give the title compounds as a mixture of 2 regioisomers (112 mg, 22.82%) and as a yellow oil. ES/MS (m/z): 266 (M+ 1). TFA (2 mL, 26.45 mmol) is added to racemic tert-butyl N-[2-(4-cyclopropylimidazol- i-yl)-i -methyl-ethyl] carbamate and to racemic tert-butyl N- [2-(5 -cyclopropylimidazol-1-yl)-1-methyl-ethyl]carbamate (112 mg, 0.2005 mmol) in DCM(10 mL) at room temperature. The mixture is stirred at room temperature for 1 hour andis concentrated to give the crude title compounds as a mixture of regioisomers (69.8 mg,100%) as a yellow oil. ES/MS (m/z): 166 (M+1). Sodium triacetoxyborohydride (56.9 mg, 0.260 mmol) is added to a solution of racemi c-i -(4-cyclopropylimidazol -1 -yl)propan-2-amine and racemic- 1 -(5- cyclopropylimidazol- 1 -yl)propan-2-amine (69.7 mg, 0.200 mmol) and tert-butyl N-(2- oxoethyl)carbamate (33.6 mg, 0.200 mmol) in DCM (5 mL) and acetic acid (15.6 mg, 0.260 mmol) at room temperature. The mixture is stirred at room temperature for 18 hours. The reaction is quenched by the addition of saturated NaHCO3. The mixture is extracted with DCM (3x), the organic extracts are dried over Na2SO4, filtered, and concentrated to give the crude title compound as a mixture of regioisomers (130 mg, 100%) as a yellow oil. ES/MS (m/z): 309 (M+1).

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

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; LIU, Lian Zhu; WANG, Xiaoqing; WILEY, Michael Robert; (34 pag.)WO2019/50794; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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.

Synthesis of 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (1.5 g, 79.78 mmol) in DMSO (15 mL) under an argon atmosphere were added potassium carbonate (4.4 g, 31.91 mmol) and 1H-imidazole-4-carbonitrile (890 mg, 9.57 mmol) at room temperature. The reaction mixture was stirred at 50° C. for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to obtain 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile (1.1 g, 56percent) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.86 (s, 1H), 8.67 (s, 1H), 8.47 (s, 1H), 4.11 (s, 3H); LCMS: 245.8 (M+1); (column; X-Select CSH C-18 (50*3.0 mm, 3.5 m); RT 2.96 min. 0.05percent aq TFA: ACN; 0.80 mL/min); TLC: 40percent EtOAc:hexane (Rf: 0.4).

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem