Month: June 2021

Related Products of 6346-09-4, 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, This compound has unique chemical properties. The synthetic route is as follows.

The compound was prepared as described in J. Chem. Soc, Perkin Trans. 1 1986, 447-453, which is hereby incorporated by reference in its entirety. [00358] 4-Aminobutyraldehyde diethyl acetal (6.4 g, 39.7 mmol) and mesityl oxide (20 ml, 175.2 mmol) were mixed neat and stirred at room temperature for 1 hour. After this time, the reaction mixture was extracted with 2.5 M HC1 and the extract washed with ether. The aqueous layer was heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo to reduce the volume by -50%. The concentrated aqueous layer was cooled on ice and diluted with methylene chloride (-100 ml). The mixture was basified with aqueous potassium hydroxide and the layers separated. The aqueous layer was further extracted with methylene chloride (100 ml) and the combined organic extracts were washed with aqueous potassium carbonate. The organic layer was dried over potassium carbonate, filtered and concentrated. Purification by flash column chromatography, on silica gel, eluting with neat EtOAc provided the product as pale yellow oil, 3.2 g (48% yield). The mixture can also be purified by distillation from K2CO3 (instead of column chromatography) to afford the ketone in a similar yield. [00359] 1H NMR (CDC13, 300 MHz) delta: 3.02 (dt, J = 8.8, 3.6 Hz, 1H), 2.74-2.84 (m, 1H), 2.38-2.54 (m, 3H), 2.09-2.24 (m, 2H), 1.86-2.02 (m, 2H), 1.72-1.82 (m, 1H), 1.45-1.57 (m, 1H), 1.24 (s, 3H), 0.92 (s, 3H).

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); A1;,
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Application of 64115-88-4, These common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, 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.

Into a 300-mi glass reaction vessel equipped with a stirring apparatus were placed 10.0 g (42 mmol) of 1-bromo-2-(trif- luoromethoxy)benzene, 2.9 g (4.2 mmol) of dichiorobis (triphenylphosphine)palladium(II), 20.1 g (54 mmol) of 2-(tributyltin)thiophene, and 100 ml of toluene. The mixture was reacted at an internal temperature of about 100 C. for 4 hours. After the completion of the reaction, the solvent was concentrated, and then 300 ml of hexane was added to the reaction solution. Subsequently, the mixture was filtered through [silica gel:potassium carbonate=90: 10 (wt %)]. The filtrate was concentrated, and the concentrate was purified bycolumn chromatography (hexane: 100 vol %), to provide 6.6 g of Compound (3-1) in the form of a pale yellow liquid.The properties of Compound (3-1) were as follows.?H-NMR (400 MHz; CDC13); 7.09-7.14 (m, 1H), 7.27- 7.37 (m, 3H), 7.37-7.41 (m, 1H), 7.41-7.44 (m, 1H), 7.63-7.70 (m, 1H)

The synthetic route of 64115-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE INDUSTRIES, LTD.; Tokito, Shizuo; Kumaki, Daisuke; Shima, Hidetaka; Oda, Hiroyuki; Tanaka, Yasuhiro; Kakita, Kazuaki; Machida, Toshikazu; Yoneda, Yasuhiro; Omata, Youji; Shimano, Tetsuro; (55 pag.)US9290516; (2016); B2;,
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Reference of 1535-73-5, These common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, 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: A solution of corresponding aniline (9.32mmol) and diethyl ethoxymethylenemalonate (9.32mmol) in ethanol (20mL) was heated at 90C for 18h. After the solvent was removed under reduced pressure, the residue was extracted with ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by open column chromatography (eluent: n-hexane/ethyl acetate=4 : 1) to give corresponding compound 16-27.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mori, Shuichi; Iinuma, Hiroto; Manaka, Noriaki; Ishigami-Yuasa, Mari; Murayama, Takashi; Nishijima, Yoshiaki; Sakurai, Akiko; Arai, Ryota; Kurebayashi, Nagomi; Sakurai, Takashi; Kagechika, Hiroyuki; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 837 – 848;,
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Related Products of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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.

A mixture of 4-bromo-2-methoxyaniline (208 mg, 1.03 mmol), 1 ,2,4-triazole (80 mg, 1.13 mmol), Cs2CO3 (0.67 g, 2.06 mmol) and Cul (20 mg, 0.103 mmol) in DMF was heated at 110 oC for 20 h. Further portions of 1,2,4-triazole (0.1 g, 1.44 mmol), Cs2CO3 (0.67 g, 2.06 mmol) and Cul (0.1 g, 0.52 mmol) were added and the mixturewas heated a further 72 h at 110 oC. The mixture was cooled, diluted with ethyl acetate (20 mL) and washed with water (2 x 20 mL). The combined aqueous washes were reextracted with ethyl acetate (20 mL). The combined organics were passed through a phase separation cartridge and the solvent removed under reduced pressure. Purification of the residue via silica gel column chromatography (0-100% ethyl acetate isohexane)gave 2-methoxy-4-(1H-1,2,4-triazol-1-yl)aniline as a light red solid (92 mg, 47%). ?H NMR (400 MHz, CDC13): oe 8.41 (s, 1H); 8.05 (s, 1H); 7.11 (d, J = 2.3, 1H); 6.99 (dd, J = 8.3, 2.3, 1H); 6.74 (d, J = 8.3, 1H); 3.97 (s, 2H); 3.92 (s, 3H).

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; CHAMBERS, Mark; CHAN, Bryan K.; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/79495; (2013); A1;,
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Application of 578-57-4, These common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, 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: A 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 × 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.

Statistics shows that 1-Bromo-2-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 578-57-4.

Reference:
Article; Yi, Zhou; Huang, Manna; Wan, Yiqian; Zhu, Xinhai; Synthesis; vol. 50; 19; (2018); p. 3911 – 3920;,
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Related Products of 4342-46-5, These common heterocyclic compound, 4342-46-5, name is 4-Methoxycyclohexanamine, 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 of 7a-d (1.0 equiv.) and amine (2.0 equiv.) in dioxane was added glacial acetic acid (0.2 equiv.), then the mixture was stirred and heated at 110 C in a sealed tube for 10-20 h. The mixture was concentrated under vacuum, and the residue was purified by column chromatography on silica gel, using petroleum ether/ethyl acetate to afford target products 8-25.

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

Reference:
Article; Zhang, Dongfeng; Liu, Yang; Zhang, Chunlin; Zhang, Hao; Wang, Bin; Xu, Jian; Fu, Lei; Yin, Dali; Cooper, Christopher B.; Ma, Zhenkun; Lu, Yu; Huang, Haihong; Molecules; vol. 19; 4; (2014); p. 4380 – 4394;,
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Synthetic Route of 20781-20-8, 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 20781-20-8 as follows.

To a solution of ethyl (4aS)-l-(4-fluorophenyl)-6-oxo-4,5,7,8-tetrahydrobenzo[f]indazole-4a- carboxylate (lg) (3.16 g, 8.92 mmol) and (2,4-dimethoxyphenyl)methanamine (2.68 mL, 17.8 mmol) in DCE (40 mL) was added acetic acid (1.54 mL, 26.8 mmol). After the reaction was stirred at rt for 5 min and cooled down in an ice-bath, sodium triacetoxyborohydride (5.l0g, 24.1 mmol) was added in portions. 5 Minute later, the reaction solution was allowed to warm to rt and continued stirring for 30 min. The solution was quenched (sat. aq. NaHCCE) and extracted (EtOAc). The organic layers were washed (brine), dried (Na2SC>4) and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (0%-75% EtO Ac/hexanes, a gradient elution) to provide the title compound (4a) (4.15 g, 92% yield) as an off-white solid m/z (ESI, +ve ion) = 506.3 [M+H]+

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; REW, Yosup; SUN, Daqing; YE, Qiuping; ZHOU, Haiying; KAWAI, Hiroyuki; MOORE, Jared; PHAM, Johnny; WU, Kejia; ZHU, Liusheng; (116 pag.)WO2020/76999; (2020); A1;,
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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. 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,2-Dibromo-4,5-dimethoxybenzene

a) Preparation of 4′,5′-Dimethoxy-[1,1′:2′,1″-terphenyl]-4,4″-dicarbonitrile A flask containing 4,5-dibromoveratrole (407 mg, 1.375 mmol), 4-cyanophenylboronic acid (606 mg, 4.125 mmol), Pd(PPh3)4 (159 mg, 0.1375 mmol), and Na2CO3 (729 mg, 6.875 mmol) was degassed and dioxane (6 mL) and H2O (3 mL) were added. Reaction was refluxed at 102 C. overnight then cooled to RT and diluted with EtOAc. Solution was washed with saturated NaHCO3 solution followed by brine and organic layer was collected, dried over Na2SO4, and concentrated. Chromatography using ISCO max gradient 50% EtOAc/hexane yielded product as a light yellow solid (467 mg, quantitative); 1H NMR (400 MHz) (CDCl3) delta 7.46-7.44 (m, 4H), 7.14-7.12 (m, 4H), 6.83 (s, 2H), 3.89 (s, 6H); 13C NMR (100 MHz) (CDCl3) delta 149.4, 145.6, 132.0, 131.3, 130.6, 118.7, 113.5, 110.6, 56.2.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LaVoie, Edmond J.; Arnold, Eddy; Bauman, Joseph D.; Kerrigan, John E.; Parhi, Ajit K.; Das, Kalyan; Kelley, Cody; Patel, Dishaben V.; US2015/322022; (2015); A1;,
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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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

General procedure: In an oven-dried Schlenk tube 2-iodophenol 6 (0.5 mmol), terminalalkyne 4 (0.5 mmol), PdO/MWCNT (5 mol%), K2CO3(1 mmol) and solvent (DMSO) (1.0 mL) were added. Theresulting reaction mixture was stirred at 120 C for 24 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was allowed to coolto room temperature, then diluted with (10 mL) ethyl acetateand NH4Cl (10 mL) was added fallowed by extraction withethyl acetate. The organic layers were dried (Na2SO4) andconcentrated in vacuum. Purification of the residue by silicagel column chromatography using petroleum ether/ethylacetate as the eluent furnished the benzofuran 7.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lakshminarayana, Bhairi; Mahendar, Lodi; Chakraborty, Jhonti; Satyanarayana, Gedu; Subrahmanyam, Ch; Journal of Chemical Sciences; vol. 130; 5; (2018);,
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Adding a certain compound to certain chemical reactions, such as: 4344-55-2, name is 4-Butoxyaniline, 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 4344-55-2, name: 4-Butoxyaniline

Example 303-(4-Butoxyphenyl)-2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one; Ethyl 2-isothiocyanato-1H-pyrrol-3-carboxylate (400 mg) obtained by the method of Reference Example 36, or a method pursuant to thereto, and 4-butoxyaniline (330 mg) obtained by the method of Reference Example 12, or a method pursuant to thereto, were added to acetonitrile (5 ml). The resulting mixture was stirred for 4 hours at 70 C., and then was concentrated under reduced pressure, to obtain a crude solid. This crude solid was added to a solution of potassium tert-butoxide (440 mg) in ethanol (5 ml), and the resulting mixture was stirred for 24 hours at room temperature. Subsequently, 1 M hydrochloric acid was added thereto until the pH value reached 6. A solid precipitated therefrom was collected by filtration, washed with water and petroleum ether, and then dried under reduced pressure, and thus the title compound (254 mg) was obtained.MS(ESI+):316(M+H).

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

Reference:
Patent; Suzuki, Hideo; Fujimoto, Takuya; Yamamoto, Takeshi; US2010/190747; (2010); A1;,
Ether – Wikipedia,
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