Month: August 2021

Reference of 6443-69-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6443-69-2 name is 1,2,3-Trimethoxy-5-methylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Reference Example 3 To a solution of 18-acetoxy-n-octadecanoyl chloride (11 g) in 1,2-dichloroethane (50 ml) is added aluminum chloride (7 g) and the mixture is stirred at room temperature for 2 hours. This reaction mixture is cooled to 5 C. and a solution of 3,4,5-trimethoxytoluene (6.2 g) in 1,2-dichloroethane (20 ml) is added. The mixture is stirred at room temperature for 72 hours. Then, this reaction mixture is heated to 50 C.-60 C. and stirred for 30 minutes. After cooling, ice-water is added to the reaction mixture and the product is extracted with dichloromethane. The dichloromethane layer is washed with water and the solvent is distilled off to recover an oil (12.1 g). This oil is dissolved in methanol (150 ml) followed by addition of sodium hydroxide (5.2 g). The mixture is stirred at room temperature for 2 hours, at the end of which time it is neutralized with 5N–HCl and the solvent is distilled off. The resultant crude crystals are rinsed with water and recrystallized from dichloromethane-ether (1:1). The above procedure yields 6-(18-hydroxy-1-oxooctadecyl)-2,3-dimethoxy-5-methylphenol (6.4 g) as colorless needles, m.p. 101 C. Elemental analysis for C27 H46 O5. Calcd. C, 71.96; H, 10.29. Found C, 72.08; H, 10.51.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2,3-Trimethoxy-5-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4495104; (1985); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 13101-88-7,Some common heterocyclic compound, 13101-88-7, name is 6-Methoxynaphthalen-2-amine, molecular formula is C11H11NO, 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.

28.2 g (0.16 mol) of the product synthesised in the previous step are dissolved in a mixture of dichloromethane/methanol: 1500/620 ml. To the resulting solution add, at ambient temperature, 56.7 g (0.16 mol) of benzyltrimethylammonium dichloroiodate and 21.2 g (0.212 mol) of calcium carbonate. After 30 minutes, filter off the insoluble material, then take up the organic phase with 10% sodium bisulphite solution and extract with ethyl ether. Dry over magnesium sulphate, filter and then evaporate. The residue is purified by chromatography over silica gel using a mixture of cyclohexane/ethyl acetate:70/30:v/v as eluant.

The synthetic route of 13101-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lavielle, Gilbert; Muller, Olivier; Millan, Mark; Gobert, Alain; Di Cara, Benjamin; US2005/59675; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 592-55-2, A common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, molecular formula is C4H9BrO, 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.

Compound A2 (0.13 mmol, 50 mg), and 1-BROMO-2-ETHOXY-ETHANE (0.65 mmol, 99 mg) were dissolved in DMF (1 ML) and triethylamine (0.91 mmol, 127 GEL). The reaction was heated in a microwave at 80C for 20 minutes. The mixture was quenched with water and extracted with ethyl acetate. Removal of organic solvent in vacuo and purification by prep-TLC provided Compound A12 as a yellow solid (20 mg, 33%).’H NMR (400 MHz, CDC13) 8 (PPM) : 10.06 (s, 1H), 8.29 (s, 1H), 7.84 (d, 2H), 7.74 (d, 2H), 5.39 (s broad, 1H), 3.53 (M, 2H), 3.39 (q, 2H), 2.86 (s, 3H), 2.77 (M, 2H), 2.65 (M, 3H), 2.04 (M, 2H), 1.92 (m, 3H), 1.09 (M 3H). LCMS (ESI), m/z 466.3 (M+H+, 100%).

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; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
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Electric Literature of 1758-46-9, These common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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.

d) (8-Bromo-6-chloro-4-methyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine 8-Bromo-6-chloro-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (141 mg, 0.33 mmol) and 2-phenoxyethyl amine (53.5 mg, 0.39 mmol) were dissolved in acetonitrile (1 ml) and heated to 200° C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution, methylene chloride and 5 to 7 drops of 30percent aqueous hydrogen peroxide solution. After the reaction has ceased the layers were separated and the aqueous phase was extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, the solvent was evaporated and the residue was purified by column chromatography (CH2Cl2:MeOH:aq conc NH3=9:1:0.1) to yield the title compound as an off-white solid (60 mg, 47percent). (MS: n/e=394.0, 396.0, 398.1 [M+H+]). 1H NMR (CDCl3): delta 1.22 (3H, d); 3.64 (2H, q), 4.12 (2H, t), 4.47 (2H, q), 6.25 (t, 1H), 6.50 (1H, s) 6.89-7.03 (4H, m), 7.25-7.31 (2H, m), 7.35 (1H, s).

The synthetic route of 1758-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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: A solution of bromo heteroaryl carboxylic acid (2mmol), thionyl chloride (4mmol) and DMF (5 drops) in toluene (10mL) was refluxed at 110C for 4h. The reaction mixture was cooled to room temperature and the solvent and the excess of thionyl chloride removed under reduced pressure. To the residue was added at 0C the corresponding N-methyl amine (2mmol) and Et3N (2mmol) in CH2Cl2 (10mL) under N2 atmosphere. After 30min at 0C, the ice bath was removed and the solution was warmed up and stirred at room temperature overnight. The reaction mixture was extracted twice with CH2Cl2 (2×15mL) and the organic layer dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexanes and EtOAc as eluant or by trituration in a mixture of diethyl ether/petroleum ether to afford the desired compound.

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perspicace, Enrico; Cozzoli, Liliana; Gargano, Emanuele M.; Hanke, Nina; Carotti, Angelo; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 317 – 337;,
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Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, belongs to ethers-buliding-blocks 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 75148-49-1, Quality Control of 3-Bromobenzaldehyde Diethyl Acetal

Step 1: Preparation of 3-(3-fluorooxetan-3-yl)benzaldehyde 3-Bromobenzaldehyde diethyl acetal (1 mL, 4.9 mmol) in dry THF (10 mL) at -78 C. was added 1.6M n-butyl lithium in hexanes (3.4 mL, 5.4 mmol) dropwise. The reaction mixture was stirred at -78 C. for fifteen minutes then added oxetan-3-one (0.353 g, 4.9 mmol) dropwise. The reaction mixture was stirred at -78 C. for thirty minutes. The reaction mixture was diluted with 50 mL saturated ammonium chloride solution and 50 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate, concentrated under reduced pressure to give the desired product, and purified by silica gel chromatography with a gradient to 50% ethyl acetate/hexanes. The crude mixture was dissolved in dry dichloromethane (10 mL), cooled to -78 C., and added diethylaminosulfur trifluoride (0.16 mL, 1.1 mmol) dropwise. The reaction mixture was stirred at -78 C. for thirty minutes. The reaction mixture was warmed to room temperature. The reaction mixture was diluted with 50 mL 1M sodium hydroxide and 50 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography with a gradient to 30% ethyl acetate/hexanes to give the desired product as a clear colorless oil (0.051 g, 0.28 mmol). 1H NMR (400 MHz, dichloromethane-d2) delta 10.10 (s, 1H), 8.13-8.10 (m, 1H), 7.96-7.92 (m, 1H), 7.92-7.88 (m, 1H), 7.72-7.66 (m, 1H), 5.20

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; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., SDS of cas: 54314-84-0

General procedure: Under an argon atmosphere,methyl 2-(4-hydroxyphenyl)acetate (3.51 g, 21.14 mmol) and caesium carbonate (13.78 g, 42.28 mmol)were suspended in dimethylformamide (130 mL), the mixture was stirred at ambient temperaturefor 2 h. Benzyl-2-bromoethylether (5.00 g, 23.25 mmol) was added and it was stirred at ambienttemperature for further 12 h. Water (250 mL) and ethyl acetate (250 mL) were added and the resultingphases separated. The organic phase was dried over sodium sulfate and concentrated in vacuum.Purification by chromatography on silica gel (gradient: 0?100percent ethyl acetate in cyclohexane) affordedthe title compound 8a as a white solid (5.30 g, 84percent yield)

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:
Article; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 702-24-9,Some common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, molecular formula is C9H13NO, 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.

(4-Methoxyphenyl)-N-methylmethanamine (0.56 g, 3.75 mmol) and DBU (0.52 mL, 3.75 mmol) were added to a solution of Example A10 (0.98 g, 2.68 mmol) in NMP (10 mL) and the mixture was heated under Ar at 155° C. for 24 h. The mixture was cooled to RT, poured into water (50 mL) and extracted with EtOAc (2*). The combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by chromatography (EtOAcDCM) to afford 7No.4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-isopropyl-1,6-naphthyridin-2(1H)-one (0.78 g, 60percent yield) as a white foam. MS (ESI) m/z: 481.0 (M+H+)

The synthetic route of 702-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 363-47-3,Some common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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 relevant halogenated heterocycle (1.0equiv.), substituted aniline (2.0 equiv.) and TFA (5.0 equiv.) were takenup in TFE (0.1 M) and heated under microwave irradiation conditionsat 140 C for 30 min before being concentrated in vacuo. The residuewas resuspended in EtOAc:THF (1:1, 20 mL/mmol), washed with saturatedNaHCO3 solution (20 mL/mmol), and the aqueous phase wasfurther extracted with EtOAc:THF (1:1, 3 × 15 mL/mmol). The combinedorganic extracts were washed with brine, dried (MgSO4) andconcentrated in vacuo. The resultant residue was purified via columnchromatography and/or triturated as specified to afford the desired compound.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Casalvieri, Kimberly A.; Matheson, Christopher J.; Backos, Donald S.; Reigan, Philip; Bioorganic and Medicinal Chemistry; vol. 28; 5; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H11BrO

A stirred mixture of 1-benzyloxy-3-bromo-benzene (10.56 g, 40.1 mmol) and dry THF (35 mL) was cooled to -78 C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (17.7 mL, 44.1 mmol) and stirred for 20 min. Then a mixture of 3,5-dimethoxy-benzaldehyde (7.34 g, 44.1 mmol) in dry THF (30 mL) was added and stirred for 1 hour at -78 C. The mixture was quenched with isopropanol (18.5 mL, 241 mmol) and added water (30 mL). The mixture was extracted with EtOAc (3*80 mL). The combined organic phases were washed with water (2*80 mL), dried over MgSO4 and concentrated to oil, which was purified by flash column chromatography (EtOAc/Hexane) to give (3-benzyloxy-phenyl)-(3,5-dimethoxy-phenyl)-methanol as an oil (11.54 g, 82% yield): 1H NMR (CDCl3) delta 2.21 (d, J=4 Hz, 1H, OH), 3.76 (s, 6H, 2OCH3), 5.04 (s, 2H, CH2), 5.72 (d, J=4 Hz, 1H, CH), 6.36 (t, J=2 Hz, 1H, Ar), 6.54 (d, J=2 Hz, 2H, Ar), 6.85-7.04 (m, 3H, Ar), 7.21-7.43 (m, 6H, Ar).

According to the analysis of related databases, 53087-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Celgene Corporation; US2005/107339; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem