Tag: M.W=100-200

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. 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 705-09-9

A solution of cyanuric chloride (922 mg, 5 mmol) in acetone (5 mL) was added to ice. A solution of 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (750 mg, 5 mmol) and triethylamine (2.1 mL, 15 mmol) in aqueous acetone was then added. After 20 min the precipitate was collected to give 1.0 g of a white powder which was a 7:3 mixture of 3-(4,6-dichloro-1,3,5-triazine-2,4-diyl)-8-oxa-3-azabicyclo[3.2.1]octane and 3,3?-(6-chloro-1,3,5-triazine-2,4-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane). Treatment of the mixture (400 mg) with 2-(difluoromethyl)-1H-benzo[d]imidazole (146 mg, 0.87 mmol) and K2CO3 (967 mg, 7 mmol) in DMF (2.5 mL) for 18 hours, followed by addition of 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (150 mg) gave, after 1 h, 3,3?-(6-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane) after purification by HPLC. (M+H) 475.

The synthetic route of 705-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH LLC; VENKATESAN, Aranapakam Mudumbai; CHEN, Zecheng; DEHNHARDT, Christoph Martin; DOS SANTOS, Osvaldo; DELOS SANTOS, Efren Guillermo; ZASK, Arie; VERHEIJEN, Jeroen Cunera; KAPLAN, Joshua Aaron; RICHARD, David James; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; GOPALSAMY, Ariamala; CURRAN, Kevin Joseph; SHI, Mengxiao; (113 pag.)US2017/119778; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, molecular formula is C8H9N3, 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: C8H9N3

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2×). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2×). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5805-57-2, its application will become more common.

Reference:
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

N-(4-Fluorobenzyl)-3-hydroxy-10-(((4-((1-methyl-1H-imidazol-5-yl)methyl)-1-piperazinyl)(oxo)acetyl)amino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide. To a solution of 7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide, 10-[[1,2-dioxo-2-(1-piperazinyl)ethyl]amino]-N-[(4-fluorophenyl)methyl]-4,6,7,8,9,10-hexahydro-3-hydroxy-4-oxo- (0.025 g, 0.040 mmol) in 1,2-dichloroethane (1 mL) and diisopropyl ethylamine (6.97 muL, 0.040 mmol) cooled to 0 C. was added 1-methyl-1H-imidazole-5-carbaldehyde (4.39 mg, 0.040 mmol) and the mixture stirred at 0 C. for 15 min. Acetic acid (2.284 muL, 0.040 mmol) and sodium triacetoxyborohydride (9.30 mg, 0.044 mmol) were added and the mixture stirred at room temperature for 4 h. The solvent was removed under a stream of air and the residue purified by preparative HPLC: Solvent A=10% methanol/90% H2O/0.1% trifluoroacetic acid; Solvent B=90% methanol/10% H2O/0-1% trifluoroacetic acid; Start % B=0; Final % B=100; Gradient time=15 min; Stop time=15 min; Column=Sunfire 19×100 mm, C18, 5 mum to give the title compound as a trifluoroacetic acid salt as a purple solid (14.7 mg, 49% yield). 1H NMR (500 MHz, MeOD) delta: 9.67 (1H, brs), 8.94 (1H, brs), 8.86 (1H, brs), 7.60 (1H, brs), 7.32-7.48 (2H, m), 7.03 (2H, t, J=8.39 Hz), 4.56 (2H, brs), 4.19 (2H, brs), 3.77-4.08 (4H, m), 3.50-3.77 (4H, m), 2.69 (3H, brs), 2.51 (1H, brs), 2.39 (2H, d, J=5.80 Hz), 2.21 (2H, brs), 1.96 (2H, d, J=4.88 Hz), 1.74 (2H, brs). (M+H) calcd for C30H36FN8O5: 607.27; found: 607.44.

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/253677; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1848-84-6, name is 2-Ethyl-1H-benzo[d]imidazole, molecular formula is C9H10N2, 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. Application In Synthesis of 2-Ethyl-1H-benzo[d]imidazole

A mixture of 3-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)- pyrrolidine-1-carboxylic acid tert-butyl ester (44 mg, 0.10 mmol), 2-ethylbenzimidazole (17 mg, 0.11 mmol), Pd2(dba)3 (2.4 mg, 2.5 molpercent), Xphos (5.0 mg, 10 molpercent) and Cs2CO3 (51 mg, 0.16 mmol) in dioxane (1.5 mL) was purged with argon gas then heated at 120 °C, for 20 h, in a sealed tube. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3/Me0H in DCM. The resulting residue was purified by column chromatography (Si-PCC, 0-100percent EtOAc in cyclohexane) to give 646 (37 mg, 67percent) as a yellow solid. LCMS: (Method I): RT 4.34 min, [M+H]+ 533.2 1H NMR (400 MHz, CDCl3d): delta 8.01-7.97 (m, 1 H), 7.78-7.73 (m, 1 H), 7.29- 7.22 (m, 2 H), 4.55-4.10 (m, 4 H), 3.86 (t, J = 4.67 Hz, 4 H), 3.80 (s, 3 H), 3.80-3.44 (m, 4 H), 3.35 (q, J = 7.48 Hz, 2 H), 2.36 (s, 3 H), 1.49 (s, 9 H), 1.44 (t, J = 7.48 Hz, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1848-84-6, its application will become more common.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, These common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-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.

General procedure: To a solution 5-bromo-1-methyl-(1H)-imidazole (180mg, 1.13 mmol) in THF (10 mL) HMPA (Hexamethylphosphoramide)was added (130 mg, 0.75 mmol) followed by t-BuLi (170 mg, 2.6 mmol) at -78oC, the resulted mixture wasallowed to stir at rt for 1 h. Then it was cooled back to -78oCand amidosulphone 4a-4j (0.75 mmol) was added in THF (5mL) slowly. The reaction mixture was slowly allowed to stirat rt for 2 h. Then, the reaction mixture was quenched withNH4Cl and extracted into EtOAc. The combined organiclayers were dried over Na2SO4 and distilled in vacuum to getcrude compounds 5a-5j and were purified by column chromatography using 5 % MeOH in DCM to get the final compounds5a-5j with 59-65 % yield.

Statistics shows that 5-Bromo-1-methyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1003-21-0.

Reference:
Article; Thripuram, Vijaya Durga; Bollikolla, Hari Babu; Mule, Siva Nagi Reddy; Battula, Sailaja Kumari; Ala, Vasu Babu; Letters in Organic Chemistry; vol. 15; 7; (2018); p. 569 – 574;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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 570-22-9, Safety of 1H-Imidazole-4,5-dicarboxylic acid

100 ml of methanol was added into 1H-imidazole-4,5-dicarboxylic acid (10 g, 64 mmol, 1 eq), and then the mixture was cooled to -9 C. in a low temperature cooler and added with thionyl chloride (5 to 10 eq). The mixture was then heated gradually to a reflux temperature and refluxed with stirring over-night, until it turned from a white turbid solution into a colorless transparent liquid. The solvent was then removed from the mixture by a rotary evaporator with a water pump in a water bath of 40 C. and thereby a white solid was obtained. The solid was washed with a dilute aqueous solution of sodium hydroxide and dried in an oven at 40 C. to obtain a product (dimethyl 1H-imidazole-4,5-dicarboxylate). 1HNMR (DMSO, 500 MHz): delta 8.057 (1H,s), delta 3.815 (6H,s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; GUANGZHOU INSIGHTER BIOTECHNOLOGY CO.,LTD.; PENG, Xianfeng; QIN, Zonghua; (15 pag.)US2018/370921; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 20970-50-7, A common heterocyclic compound, 20970-50-7, name is 1-(1-Methyl-1H-imidazol-5-yl)ethanone, molecular formula is C6H8N2O, 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.

[2516] Dissolve 365 (0.24 g, 0.49 mmol) in THF (2.5 ml). Cool under N2 to -78 C., add (1) (BuLi, 2.5M, 0.2 ml) and stir the resulting dark brown solution for 15 minutes. Dissolved 883 (0.116 g) from Step C in 0.5 mL of THF and add to reaction and stir at -78 C. for 3 hours. Add reaction mixture to brine and extract with ethyl acetate(2×). Dry with MgSO4, filter and evaporate to obtain a yellow solid. Purified crude (0.29 g) by Prep Plate Chromatography to afford 0.0.15 g, 42% yield of the desired product (795.1).

The synthetic route of 20970-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 716-79-0, name is 2-Phenyl-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 716-79-0, category: imidazoles-derivatives

General procedure: A mixture of diazabicyclic olefin (50 mg, 0.2083 mmol,1.0 eqiuv), N-phenylpyrazole (30 mg, 0.2083 mmol, 1.0 eqiuv), [RuCl2(p-cymene)]2 (6 mg, 0.0104 mmol, 5.0 mol percent), and Cu(OAc)2H2O (62.46 mg,0.3123 mmol, 1.5 equiv) was weighed in a Schlenk tube and degassed for10 min. Dry toluene (2 mL) was added and the reaction mixture was purged with argon and allowed to stir at 110 °C for 12 h. The reaction mixture on silicagel column chromatography using mixtures of EtOAc?hexane yielded functionalized cyclopentene 3a in 73percent yield (58 mg).

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:
Article; Aparna; Prabha; Prakash, Praveen; Jijy; Luxmi Varma; Radhakrishnan; Tetrahedron Letters; vol. 55; 4; (2015); p. 865 – 868;,
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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H5ClN2O2S

To a solution of tert-butyl 8-amino-5-(ethylsulfonyl)-1,3,4,5-tetrahydro-2H- pyrido[4,3-b]indole-2-carboxylate (0.26 mmol) in dry dichloromethane (8 mL) was added 1-methyl-1H-imidazole-4-sulfonyl chloride (0.32 mmol) followed by triethyl amine (0.52 mmol), the reaction mixture was stirred at room temperature for overnight and diluted with dichloromethane (20 mL), washed with saturated NaHCO3 solution (10 mL), dried over Na2SO4. The solution was concentrated in vacuo and the EPO crude product was used for the next step without farther purification. MS (M+l): 524.0.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 137049-00-4.

Reference:
Patent; AstraZeneca AB; WO2006/101434; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

Example 29 3-(5-Methyl-3H-imidazol-4-ylmethylene)-4-piperidin-4-yl-1,3-dihydroindol-2-one, Acetic Acid Salt A mixture of 4-piperidin-4-yl-1,3-dihydroindol-2-one (124 mg, 0.57 mmol) and 5-methyl-3H-imidazole-4-carbaldehyde (62.8 mg, 0.57 mmol) in ethanol (3 mL) was stirred at room temperature for 2 days. The reaction was concentrated and the residue was column chromatographed (reverse phase) to give 23 mg of the title compound as a yellow acetic acid salt. 1H NMR (300 MHz, DMSO-d6) delta 13.89 (br s, 1H, NH), 11. 02 (br s, 1H, NH), 7.90 (s, 1H), 7.52 (s, 1H), 7.15 (t, J 7.8 Hz, 1H), 6.93 (d, J=7.8 Hz, 1H), 6.76 (d, J 7.8 Hz, 1H), 3.20 (m, 1H), 3.15 (m, 2H, CH2), 2.73 (m, 2H, CH2), 1.86 (m, 3H, CH3), 1.84 (m, 2H, CH2), 1.62 (m, 2H, CH2). MS m/z 309 [M++1].

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; Tang, Peng Cho; Wei, Chung Chen; Huang, Ping; Cui, Jingrong; US2002/187978; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem