Category: ethers-buliding-blocks

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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Methoxy-N-methylbenzylamine

A mixture of 3-(5-amino-2-chloro-4-fluorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (2.5 g, 7.4 mmol) and 4-methoxy-N-methylbenzylamine (4 mL) was heated to 180¡ã C. under N2 for 3 h. After cooling, the reaction mixture was diluted with Et2O. The precipitate was filtered, washed with water, and dried to give 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 89percent yield). 1H NMR (400 MHz, DMSO-d6): delta 8.47 (s, 1H), 7.77 (s, 1H) 7.22 (m, 2H), 7.17 (d, J=8.0 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 5.86 (d, J=9.6 Hz, 1H), 6.30 (s, 1H), 5.32 (s, 2H) 4.87 (s, 1H), 3.72 (s, 3H), 3.52 (s, 3H), 3.09 (s, 3H); MS (ESI) m/z: 453.2[M+H]+.

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; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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Application of 1836-62-0, 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. 1836-62-0 name is 2-(2-Methoxyphenoxy)ethylamine, 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.

Step 2: Synthesis of 2-{4-[3-(2-methoxyphenoxyethylamino)propoxy]phenyl}3- (3,5-dimethoxyphenyl)acrylic acid methyl esterA suspension of 2-[4-(3-bromopropoxy)phenyl]-3-(3,5-dimethoxyphenyI) acrylic acid methyl ester (0.56 g, 1.3 mmol), 2-(2-methoxyphenoxy)ethylamine (0.23 mL, 1.5 mmol) and potassium carbonate (0.53 g, 3.8 mmol) in DMF (8 mL) was heated to 80 0C for 4 hours. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate (2 x 100 mL). The ethyl acetate layer was washed with water (100 mL x 3), dried over anhydrous Na2SO4 and concentrated to afford the crude compound, which was purified by column chromatography using 2% methanol in dichloromethane as the eluent, to furnish the title compound (0.05 g, 7.5 % yield). 1H NMR (DMSO-d6) delta (ppm): 1.86-1.90 (2H, m, -CH2), 2.72-2.76 (2H, t, – CH2), 2.87-2.90 (2H, t, -CH2), 3.53 (6H, s, -OCH3), 3.70 (3H, s, -OCH3), 3.73 (3H, s, – OCH3), 3.99-4.02 (2H, t, -CH2), 4.04-4.07 (2H, t, -CH2), 6.27-6.28 (2H, d, Ar-H), 6.38- 6.39 (IH, m, Ar-H), 6.87-6.89 (2H, m, Ar-H), 6.94-6.97 (4H, m, Ar-H), 7.07-7.09 (2H, d, Ar-H), 7.67 (IH, s, =CH). MS m/z: 522.2 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Methoxyphenoxy)ethylamine, and friends who are interested can also refer to it.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LIMITED; WO2009/60282; (2009); A2;,
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Reference of 5888-51-7, 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. 5888-51-7, name is 4-Ethyl-1,2-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A sealed tube equipped with a magnetic stirring bar was charged with ethylarene (1, 1.0 mmol), aq NH3 (2, 25% aq solution,10.0 mmol), I2 (1.1 mmol), and TBHP (6.0 mmol, 70% aq solution) at r.t. The resulting mixture was heated to 100 C for 3.0 h. After completion of the reaction (monitored by TLC), sat.Na2S2O3 solution (10 mL) was added to the reaction mixture,and it was extracted with EtOAc (2 ¡Á 20 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on 100-200 mesh silica gel using EtOAc-n-hexane (1:2) as the eluent to obtain the corresponding benzamide 3.

The chemical industry reduces the impact on the environment during synthesis 4-Ethyl-1,2-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Vadagaonkar, Kamlesh S.; Kalmode, Hanuman P.; Prakash, Sattey; Chaskar, Atul C.; Synlett; vol. 26; 12; (2015); p. 1677 – 1682;,
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934240-59-2, name is 1-((4-Bromophenoxy)methyl)-2-fluorobenzene, belongs to ethers-buliding-blocks 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: 934240-59-2

To a stirred suspension of magnesium metal (9Og) in dry THF (60OmL) under a nitrogen atmosphere at room temperature was added iodine (0.3g). The mixture was heated to an internal temperature of 64 +/- 2C. A solution of 1-[(4- bromophenoxy)methyl]-2-fluorobenzene (693g) in THF (150OmL) was added in two batches. Firstly 45 mL was added. Secondly, the remaining solution (1455 mL) was added dropwise. After addition, the reaction was heated at reflux for 1 h. The reaction mixture was cooled to room temperature. This reaction mixture was then added slowly to a solution of commercially available 1-te/t-butyl 2-methyl (2S)-5-oxopyrrolidine-1 ,2- dicarboxylate (30Og) in THF (150OmL) cooled to -6O0C, maintaining the internal temperature below -600C. The addition was completed in 2 hours. The reaction mixture was stirred for a further 15 minutes after addition, lsopropyl alcohol (30OmL) was then added dropwise whilst maintaining the temperature below -600C. A mixture of aqueous saturated ammonium chloride solution/aqueous saturated sodium chloride solution (2/1 ; 90OmL) was added whilst maintaining the temperature at -500C. Water (600 ml.) was added to dissolve the yellow precipitate. The organic phase was separated and was washed with aqueous 13% NaCI solution (60OmL). The organic phase was concentrated to dryness. EtOAc (150OmL) was then added and the solution was evaporated under reduced pressure to remove water. The residue was purified by chromatography on silica gel eluting with cyclohexane / ethyl acetate (90:10 to 8:2) to afford the title compound (287 g); 1H NMR (600 MHz, DMSO-d6) delta(ppm): 7.93 (d, 2H); 7.57 (td, 1 H); 7.44 (m, 1 H); 7.27 (m, 3H); 7.14 (d, 2H); 5.24 (s, 2H); 4.04 (m, 1 H); 3.61 (s, 3H); 3.03 (m, 2H); 1.94 (m, 2H); 1.38 (s, 9H).

The synthetic route of 934240-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/90114; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 768-70-7, name is 3-Ethynylanisole, 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 768-70-7, category: ethers-buliding-blocks

General procedure: To the mixture of terminal alkyne (1mmol), water (2.0 equiv), and acetic acid (2 mL), silver tetrafluoroborate (5 mol%) was added. The mixture was stirred at 110C for 10 h. Water (10 mL) was added and the solution was extracted with ethyl acetate (3¡Á8 mL), the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography to give the pure sample. 4.2.8. 1-(3-Methoxyphenyl)ethanone (2h). 1H NMR (400 MHz, CDCl3): delta=7.41-7.47 (m, 2H), 7.26-7.31 (m, 1H), 7.02-7.04 (m, 1H), 3.77 (s, 3H), 2.51 (s, 3H). 13C NMR (100 MHz, CDCl3): delta=197.7, 159.7, 138.4, 129.5, 121.0, 119.4, 112.3, 55.3, 26.6. MS (EI) m/z: 150, 135, 107, 92, 77, 63.

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

Reference:
Article; Chen, Zheng-Wang; Ye, Dong-Nai; Qian, Yi-Ping; Ye, Min; Liu, Liang-Xian; Tetrahedron; vol. 69; 30; (2013); p. 6116 – 6120;,
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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. 1579-40-4, name is Di-p-tolyl Ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Di-p-tolyl Ether

1.9827 g (0.01 mol) of dissolved p-tert-phenyl ether,0.01883 g (1 mol%) of Tris derivative modifiedFe-Anderson type polyacid ([N(C4H9)4] 3[FeMo6O18{(OCH 2)3CNH2}2]),0.0106 g (0.1 equiv) of sodium carbonate additive,30% by weight of hydrogen peroxide containing 0.03 moles of hydrogen peroxide and 30 ml of solvent diethyl malonate are put into a dry and clean pressure tube.After heating to 100 C,After 18 hours of heat treatment under a pressure (gauge pressure) of 1.0 MPa,Stop the reaction,The reaction system was extracted 3 times with ethyl acetate.The obtained product is removed under reduced pressure,Column chromatography to obtain 4,4′-diphenyl ether dicarboxylic acid,Obtained 2.3983 grams of product,The yield was 93%.

The synthetic route of 1579-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Technology; Yu Han; Wang Jingjing; He Huihong; (8 pag.)CN108484381; (2018); A;,
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Application of 93-04-9, These common heterocyclic compound, 93-04-9, name is 2-Methoxynaphthalene, 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 1 The following is a procedure for preparing 2-methoxy-6-ethylnaphthalene by the transethylation of 2-methoxynaphthalene. To a 250 ml., 3-neck, round-bottom flask equipped with a magnetic stirrer and a sparge tube were added 70 g of mixed diethylbenzenes obtained from the Aldrich Chemical Company, Milwaukee, Wis. After cooling the reaction mixture with an ice bath, hydrogen chloride gas was added for three minutes and thereupon 14.48 grams of aluminum chloride were slowly added. Hydrogen chloride gas was again added for three minutes. The reaction flask was then placed in a hot water bath to raise the temperature of the reaction mixture to 85-90 C. At this point ethylene gas was sparged into the reaction mixture until the level of tetraethylbenzene in the reaction mixture was maximized. The composition of the mixture was monitored by gas chromatography. After the ethylene addition was stopped, the reaction mixture was stirred for an additional 30 minutes at 90 C. To the above reaction mixture at 15 C. was added a mixture of 29.02 grams of 2-methoxynaphthalene dissolved in 50 ml of dichloromethane. The reaction mixture was permitted to warm to room temperature and after 900 minutes it was heated to 32 C. using a water bath. After 15 hours total reaction time the yield of 2-methoxy-6-ethylnaphthalene was 71.5% as measured by gas chromatography. This example shows the high yield of 2-methoxy-6-ethylnaphthalene that can be achieved by the method of this invention.

Statistics shows that 2-Methoxynaphthalene is playing an increasingly important role. we look forward to future research findings about 93-04-9.

Reference:
Patent; Amoco Corporation; US5235115; (1993); A;,
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Application of 70627-52-0, A common heterocyclic compound, 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, molecular formula is C20H16FNO, 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.

Preparation of TiCl4+Ti(O-i-Pr)4 mixed solution:The TiCl4 (21.3g, 0.112mol) dissolved in 100ml dichloromethane.Ti(O-i-Pr)4 (10.6 g, 0037 mol) was added dropwise at 0 C.The reaction was kept for 30 minutes.Intermediate A1-2 (53.4 g, 0.1 mol) andIntermediate A1-3 (61.4 g, 0.2 mol)Soluble in 250ml dichloromethane,DIPEA (25.8g, 0.2mol) was added dropwise at -15 C.TiCl4+Ti(O-i-Pr)4 mixed solution,After the addition is completed, the reaction is continued for 2 hours.Then glacial acetic acid (30 g, 0.5 mol) was added dropwise.After cooling in an ice bath, the reaction solution was poured into a 7% aqueous solution of tartaric acid.Stir for 1 h, naturally warm to room temperature,Add 100ml of 20% sodium bisulfite solution,Stirring was continued for 2 h, the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated.50 ml of methanol was beaten and the white solid was 62.1 g.

The synthetic route of 70627-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuxi Fuqi Pharmaceutical Co., Ltd.; Wang Qinglin; Wang Tao; Wang Binbin; Sun Yilin; (11 pag.)CN109369491; (2019); A;,
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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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 111-95-5

Into a 10-mL vial, was placed a solution of bis(2-methoxyethyl)amine (285.6 mg, 2.15 mmol, 3.00 equiv) in N,N-dimethylformamide (3 mL), and N,N-diisopropylethylamine (277 mg, 2.14 mmol, 2.99 equiv). This was followed by the addition of a solution of N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide (300 mg, 0.72 mmol, 1.00 equiv) in N,N-dimethylformamide (2 mL). The resulting solution was stirred for 48 h at 80 C. in an oil bath. The reaction progress was monitored by LCMS. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 3*50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2*70 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:5?1). The product was obtained as 270 mg (71%) of a yellow to green oil.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
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Synthetic Route of 592-55-2, 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. 592-55-2, name is 1-Bromo-2-ethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of 22 (30 mg, 0.081 mmol) in DMF (3 mL) were added K2CO3 (170 mg, 1.20 mmol), NaI (180 mg, 1.20 mmol) and 2-bromoethyl methyl ether (75 muL, 0.81 mmol), and stirred at 100 C under an Ar atmosphere. After 3 h with stirring, the reaction mixture was evaporated in vacuo. The resulting mixture was basified (pH 9) with saturated NaHCO3 aqueous solution and extracted with CHCl3 three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by preparative TLC (CHCl3/MeOH = 10:1) to give 26 (27 mg, 77%) as a colorless oil.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-ethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nemoto, Toru; Ida, Yoshihiro; Iihara, Yusuke; Nakajima, Ryo; Hirayama, Shigeto; Iwai, Takashi; Fujii, Hideaki; Nagase, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7628 – 7647;,
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