Category: imidazoles-derivatives

Application of 39021-62-0, 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 39021-62-0 as follows.

COMPOUND 12.1. 51: 4-{6,7-DIMETHOXY-3-METHYL-2-[(4-METHYL-1H- IMIDAZOL-5-YL) METHYL1-l, 2, 3, 4-TETRAHYDROISOQUINOLIN-l-YL}-N*N- DIETHYLBENZAMIDE; Methyl-imidazole-5-carboxyaldehyde (55.9 mg, 0.51 mmol) was added to a solution of INTERMEDIATE 5.1. 14 (97 mg, 0.25 mmol) in 1,2-dichloroethane (4 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (378 mg, 1.78 mmol) was added followed by N-methyl-2- pyrrolidinone (320 uL) and the reaction mixture stirred at RT for 22 h. 1 N NaOH (2.5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with DCM (3 x 10 mL) and the organic layer washed with water (10 mL). The organic layer was concentrated in vacuo and the residue purified by repeated flash chromatography on Si02 column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 51 as an oil (85.9 mg, 71%). 1H NMR (500 MHz, CDC13) : 6 1.10 (br s, 3H), 1.24 (br s, 3H), 1.45 (d, J6. 5 Hz, 3H), 2.30 (s, 3H), 3.15-3. 30 (m, 4H), 3.53 (m, 2H), 3.64 (s, 3H), 3.90 (s, 1H), 3.91 (s, 3H), 4. 49 (d, J 14.5 Hz, 1H), 4.62 (d, J 14.5 Hz, 1H), 5.59 (s, 1H), 6.26 (s, 1H), 6.74 (s, 1H), 7.21-7. 31 (m, 4H), 8.24 (s, 1H) ; 13C NMR (125 MHz, CDC13) : 8 9.28, 12.82, 14.11, 19.11, 32.83, 40.13, 43. 83, 46.93, 56.19, 56.25, 59.95, 67.61, 111. 10, 111. 24,119. 36,121. 66,123. 61, 127. 29,129. 60,132. 72, 134.35, 137.08, 137.66, 149.15, 150.07, 170.73 ; (+) LRESIMS m/z 477. 39 [M+H] +.

According to the analysis of related databases, 39021-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl-1H-imidazole-4-carboxylate (10.37 g, 74.0 mmol) in acetonitrile (200 mL) was added 2,4-dichloro-5-methylpyrimidine (10 g, 61.7 mmol) and potassium carbonate (25.5 g, 185.2 mmol), and then the mixture was stirred at RT for 16 h under an inert atmosphere. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by gradient column chromatography using ethyl acetate in hexane as eluent to afford methyl 1-(2-chloro-5-methylpyrimidin-4-yl)-1H-imidazole-4-carboxylate as a white solid (11 g, 75%). 1HNMR (400 MHz, DMSO-d6): delta 8.88 (s, 1H), 8.38 (s, 2H), 3.80 (s, 3H), 2.41 (s, 3H). LC-MS exact mass calcd 252.04, found m/z 253.2 [M+1-1]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 1H-imidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); 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. 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 106429-57-6

(b) 2,3-Dihydro-2-oxo-5-hydroxymethyl-1H-benzimidazole (20b) 24.6 g (0.128 mol) of 20a are suspended in THF and stirred with 624.8 ml (0.768 mol) of DIBAL (20% strength solution in toluene) at -70 C. overnight in analogy to Example 1a. Yield: 16.2 g (77%). C8 H8 N2 O2 (164.2). NMR (DMSO): delta=4.48 (s, 2H), 5.12 (broad s, 1H), 6.91 (s, 2H), 6.98 (s, 1H), 10.61 (broad s, 2H) ppm.

According to the analysis of related databases, 106429-57-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US4748163; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3012-80-4,Some common heterocyclic compound, 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, molecular formula is C9H8N2O, 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.

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).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, its application will become more common.

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. 3034-41-1, name is 1-Methyl-4-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-4-nitroimidazole

2, 5-Dichloro-Lambda/-(l -methyl- lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 500 mg, 3.93 mmol) was dissolved in ethanol (7.868 mL) and Pd/C (10 wt%, Degussa, 105 mg, 0.10 mmol) was added. The reaction mixture was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and 2,4,5-trichloropyrimidine (0.361 mL, 3.15 mmol) and TEA (1.097 mL, 7.87 mmol) were added. The reaction mixture was stirred overnight at rt. The reaction mixture was filtered providing the title compound as a pale yellow solid (538 mg). LCMS: 245 [M+Eta]+.

According to the analysis of related databases, 3034-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; ALMEIDA, Lynsie; CHUAQUI, Claudio, Edmundo; GUAN, Amy; IOANNIDIS, Stephanos; LAMB, Michelle; PENG, Bo; SU, Qibin; WO2010/20810; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 305790-48-1, 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. 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[000822j A stirred solution of compound 2 (0.1 g, 1 eq) in POC13 (3 mL) was heated at 110C for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was slowly basified to pH 8 using saturated sodium bicarbonate solution and extracted with ethyl acetate (2 X 25 mL). Combined organic extracts were washed with brine and dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 50% EtOAc-hexane to afford the title compound 3. LCMS (mlz): 244.95 (M + 1).

The synthetic route of 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
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 4238-71-5 as follows. Quality Control of 1-Benzyl-1H-imidazole

General procedure: Yield: 82%. Yellow oil. 1H NMR (400HMz, CDCl3, TMS) delta 10.61 (s, 1H), 7.49-7.47 (m, 2H), 7.43(s, 1H), 7.39(s, 1H), 7.34-7.32 (m, 3H), 5.59 (s, 2H), 4.27 (t, J = 6.0 Hz, 2H), 1.90-1.83 (m, 2H), 1.38-1.29 (m, 2H), 0.91(t, J = 6.0 Hz, 3H). 13C NMR (100HMz, CDCl3; TMS) delta 136.12, 134.49, 128.94, 128.68, 128.30, 122.78, 122.50, 51.79, 48.65, 31.23, 18.76, 13.24.

According to the analysis of related databases, 4238-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Shi; Wang, Binshen; Zhang, Yongya; Elageed, Elnazeer H.M.; Wu, Haihong; Gao, Guohua; Journal of Molecular Catalysis A: Chemical; vol. 418-419; (2016); p. 1 – 8;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1450-93-7, 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1) belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Aminoimidazole sulfate (659 mg) is dissolved in 0.42 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. To the solution is added 345 mg of NaNO2 in 1 mL of water dropwise so the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.0 g of 2,2,2-trifluoro-1-(4-pentyl-3,4-dihydroquinoxalin-1(2H)-yl)ethan-1-one, 0.82 g of sodium acetate and 3 mL of acetic acid is cooled to 0 C. To this slurry is added the diazonium solution slowly while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and brick red solid is collected. The crude (E)-1-(7-((1H-imidazol-2-yl)diazenyl)-4-pentyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethan-1-one is dried and used in the next step without further purification (0.94 g).

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, 1H-imidazol-2-amine sulfate(2:1), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1467-16-9,Some common heterocyclic compound, 1467-16-9, name is 1H-Imidazole hydrochloride, molecular formula is C3H5ClN2, 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.

K2CO3 (3.99 g, 28.8 mmol) and imidazole hydrochloride (1.00 g, 9.60mmol) were dissolved in MeCN (30 mL) in a round-bottomed flask. Benzyl bromide (1.25 mL, 10.6 mmol) was added dropwise to the stirred solution at r.t. After 70 h, the solution was concentrated and the materials redissolved in CH2Cl2 (i.e., CH2Cl2) and then extracted with H2O (3 × 30 mL). The organic layer was then dried (MgSO4). The product was collected as off-white coloured wax (0.63 g, 42% yield). 1H NMR spectrum is consistent with that previously reported.

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

Reference:
Article; Herasymchuk, Khrystyna; Huynh, Jennifer; Lough, Alan J.; Roces Fernandez, Laura; Gossage, Robert A.; Synthesis; vol. 48; 13; (2016); p. 2121 – 2129;,
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. 3034-38-6, name is 5-Nitro-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 5-Nitro-1H-imidazole

Example 20Preparation of 3-(4-fluorophenylsulfonyl)-N-Q-methyl-lH-imidazol-4- vDisoq uinolin- 1-amine[00277] Step A: To a mixture of 4-nitro-lH-imidazole (2.0 g, 17.7 mmol) andK2CO3 (3.67 g, 26.6 mmol) in acetonitrile (18 mL) was added iodomethane (1.32 mL, 21.2 mmol) and the mixture was heated in a sealed vial at 60 C overnight. The mixture was filtered washing with acetone. The filtrate was concentrated under reduced pressure, and the residue was diluted with hot isopropanol and cooled, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform and filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with propan-2-ol and collected by filtration to afford 1- methyl-4-nitro-lH-imidazole (1.03 g, 46%) as a tan solid. 1H NMR (300 MHz, DMSO-t/e) delta 8.37 (d, J= 1.1 Hz, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; FARAONI, Raffaella; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; SETTI, Eduardo; WO2012/30944; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem