Category: ethers-buliding-blocks

Application of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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 corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl-oxycarbonyl) amino acids 20a-h (0.47 mmol) were dissolved in 50 mL of anhydrous CH2Cl2 and cooled to 0 C. 1-Hydroxybenzotriazole (HOBt) (0.7 mmol) and EDCI (0.56 mmol) were added, and the mixture was stirred for 30 min at 0 C. Subsequently, 0.39 mmol of compound 3 and finally 2.4 mL of N-ethyl diisopropylamine were added. The mixture was stirred for 16 h at ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flask-column chromatography (gradient elution with mixtures of chloroform/methanol) on silica gel as monitored by TLC. Synthesized target compounds 21a-h were characterized by mp, IR, ESR and HRMS analyses.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, its application will become more common.

Reference:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
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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 589-10-6 as follows. SDS of cas: 589-10-6

Example 101 N’-[1-imidazol-1-yl-1-[3-(2-phenoxyethoxy)thiophen-2-yl]methylidene]-N,N-dimethylhydrazine (compound No. 101) To a solution of methyl 3-hydroxythiophene-2-carboxylate (0.992 g, 6.27 mmol) in N,N-dimethylformamide (12 ml) were added beta-bromophenetole (1.268 g, 6.31 mmol) and potassium carbonate (1.059 g, 7.66 mmol), and the mixture was stirred at 80C for 4.5 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give methyl 3-(2-phenoxyethoxy)thiophene-2-carboxylate (1.624 g, 5.83 mmol, yield 93%).

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; EP2168951; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, 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 37466-89-0, Computed Properties of C7H10N2O

Step 3: 3~but-3-en~l-yl-8-rnethoxyquinoxalin-2-ol; To a solution of 3-methoxybenzene-l ,2-diamine from step 2 (5.6 g, 40.5 mmol) inDCE (250 ml), ethyl 2-oxohex-5-enoate (9.50 g, 60.8 mmol) was added, and the mixture was stirred at 60C for 14 hours. An additional charge of ethyl 2-oxohex-5-enoate (1.45 g, 9.28 mmol) was added, and the mixture was heated for 24 hours. The reaction mixture was concentrated and filtered from CH2CI2 to remove a portion of the undesired regio-isomer as a tan solid. The filtrate was purified by column chromatography on S1O2 (gradient elution, 1-9% acetone/C?Cl2) to give the title compound as a tan solid (6.4 g, 68.6 %) after triturating with 10% Et20/hexane. LCMS (ES+) m/z 231.1 (M+H)+.

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, 3-Methoxybenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.R.L.; MCCAULEY, John, A.; LIVERTON, Nigel, J.; RUDD, Michael, T.; GILBERT, Kevin, F.; FERRARA, Marco; SUMMA, Vincenzo; CRESCENZI, Benedetta; WO2012/40040; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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 93919-56-3, category: ethers-buliding-blocks

Compound 25 (100 mg, 299.18 umol, 1.0 eq.), HATU (113.76 mg, 299.18 umol, 1.0 eq.) and triethylamine were dissolved in 2 mL of DCM in a 50 mL round-bottom flask. Compound B (114.38 mg, 598.36 umol, 2.0 eq.) was added and the reaction was kept at 25 C for 4 hours. LCMS detection reaction is complete. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by HPLC to give compound 8 as a white solid (80 mg, 157.67 umol, yield: 52.70%).

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; Shanghai Yaoming Kant, Immanuel New Drug Development Co., Ltd.; Wu Xiangyang; Wang Fei; Ao Zhiyong; Yang Kanghui; Wan Shuangyi; Wang Lijuan; (30 pag.)CN106478589; (2017); 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. 2216-69-5, name is 1-Methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2216-69-5

General procedure: 1mL [Bmim]NO3, 0.5 mmol substrate asshown in Scheme S1 and 0.25 mmolBr2 were added to a dried 45 mL tube equipped with a magneticstirring(note: the air in the tube was not removed). Then the reaction tube was sealed to perform the reaction for 24 h at 80 oC. Oncethe reaction time was reached, the mixture was cooled to room temperature and 3mL water was added. Then the desiredproduct was extracted with CH2Cl2 (3 ¡Á 10 mL). GC analysis of the mixture provided the GCyield of the product.

According to the analysis of related databases, 2216-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ren, Yun-Lai; Wang, Binyu; Tian, Xin-Zhe; Zhao, Shuang; Wang, Jianji; Tetrahedron Letters; vol. 56; 46; (2015); p. 6452 – 6455;,
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Electric Literature of 31576-51-9, These common heterocyclic compound, 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, 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.

To a solution of 4-mercapto-4-nnethylpentanoic acid (226 pl_, 251 mg, 1 .69 mmol) in CHC were added 2-(2-methoxyethoxy)ethanamine (249 mI_, 242 mg, 2.03 mmol) and N-ethyl-N’-(3- dimethylaminopropyl)carbodiimide hydrochloride (0.35 g, 1 .82 mmol). The mixture was stirred for 1.5h, heated to 60 C for 2h and subsequently stirred at rt for 3d. The reaction mixture was then purified by silica chromatography (50% EtOAc in heptane EtOAc). The desired product was obtained as a colorless oil (0.23 g, 0.29 mmol, 54%). 1 H NMR (400 MHz, CDCI3) d (ppm) 6.20- 6.00 (bs, 1 H), 3.65-3.60 (m, 2H), 3.59-3.53 (m, 4fH), 3.49-3.44 (m, 2H), 3.40 (s, 3H), 2.40-2.33 (m, 2H), 1.96-1.88 (m, 2H), 1.63 (bs, 1 H), 1 .38 (d, J = 0.5 Hz, 6H).

Statistics shows that 2-(2-Methoxyethoxy)ethanamine is playing an increasingly important role. we look forward to future research findings about 31576-51-9.

Reference:
Patent; SYNAFFIX B.V.; VERKADE, Jorge Merijn Mathieu; HOOGENBOOM, Jorin; VAN BERKEL, Maria Antonia; VAN DELFT, Floris Louis; (95 pag.)WO2019/110725; (2019); A1;,
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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. 4342-46-5, name is 4-Methoxycyclohexanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H15NO

DIPEA (3.24 mL, 18.58 mmol) was added to ethyl 2,4-dichloropyrimidine-5-carboxylate (3.42 g, 15.5 mmol) and 4-methoxycyclohexan-l -amine (2.0 g, 15.5 mmol) in acetonitrile (80 mL) at 0C. The reaction mixture was stirred at rt for 16 h. The solvent was removed under reduced pressure. The crude product was purified by fee, eluting with 0 – 5% EtOAc in petroleum ether, to afford the title compound (3.60 g, 74%) as a white solid; NMR(400 MHz, CDCls) 1.26 – 1.50 (4H, m), 1.38 (3H, t), 2.02 – 2.18 (4H, m), 3.15 – 3.27 (1H, m), 3.37 (3H, s), 4.04 – 4.18 (1H, m), 4.35 (2H, q), 8.34 (1H, d), 8.66 (1H, s); mJz MH+314.

The synthetic route of 4342-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (2018); A1;,
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Synthetic Route of 19500-02-8,Some common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-methylaniline, molecular formula is C8H11NO, 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.

To 3-methoxy-2-methyl aniline(2.74 g, 20 mmol), water (6 mL) and 48percent aqueous solution of hydrobromic acid (2.4 mL) were added. To this sodium nitrite (2.76 g, 40 mmol) in water (1.20 mL) was added dropwise at 0¡ãC for 10 minutes. After adding acetone (24 mL) to the reaction mixture, copper bromide (5.64 g, 40 mmol) was added at 0¡ãC and stirred for 3hours. The reaction mixture was warmed to room temperature and concentrated. The residue was diluted with dichloromethane and washed with a mixture of saturated aqueous sodium hydrogen carbonate and aqueous ammonia. The organic layer was dried over anhydrous sodium sulfate and the filtrate was concentrated to obtain the title compound (2.5 g, yield : 62percent); m/z (ES+) : 201 [M+H]+.

The synthetic route of 19500-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEO PHARMA A/S; BLADH, Haakon; FELDING, Jakob; ZHOU, Ding; CAI, Zhen-wei; S?RENSEN, Morten Dahl; WO2015/24878; (2015); A1;,
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Reference of 18638-99-8, 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. 18638-99-8 name is (3,4,5-Trimethoxyphenyl)methanamine, 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.

General procedure: In a 25 mL of round bottom flask, a solution of di-tert-butyldicarbonate (1 mmol) and Diphenyglycouril (10 mol %) were addedin 10 mL of ethanol. A turbid solutionwas obtained. In that solution1 mmol of Amine (1a-y) was added. Reaction mixture was stirredfor 30 min at room temperature. After total consumption of thestarting material (determination by TLC), the solvent was removedin vacuo, and the residue was isolated by column chromatographyon silica gel to get the pure product 3a-y as solid or oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3,4,5-Trimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Awasthi, Amardeep; Mukherjee, Anagh; Singh, Mandeep; Rathee, Garima; Vanka, Kumar; Chandra, Ramesh; Tetrahedron; vol. 76; 23; (2020);,
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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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-(Difluoromethoxy)aniline

To a solution of 4-difluoromethoxyphenylamine (0.99 g, 6.30 mmol) in EtOH (4.5 mL) at 20 C was added under stirring an aqueous HNO3 solution (67%, d=1.4, 0.43 mL, 6.30 mmol) followed by the addition of cyanamide (0.45 g,10.6 mmol). The resulting solution was stirred at reflux for 12 h. Then the mixture was cooled down to rt, concentrated at reduced pressure and diluted with MTBE (15 mL) to induce crystallization of the product. The resulting suspension was stirred at 20 C for 15 min. The formed precipitate was filtered off, washed with a cold mixture of MTBE/EtOH (3:1, 5 mL) followed by MTBE (5 mL), and air-dried to afford the product (0.95 g, 58%) as a white solid;

According to the analysis of related databases, 22236-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kubas, Holger; Meyer, Udo; Krueger, Bjoern; Hechenberger, Mirko; Vanejevs, Maksims; Zemribo, Ronalds; Kauss, Valerjans; Ambartsumova, Raisa; Pyatkin, Ilya; Polosukhin, Alexey I.; Abel, Ulrich; Bioorganic and Medicinal Chemistry Letters; vol. 23; 16; (2013); p. 4493 – 4500;,
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