Month: May 2021

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 202865-58-5 as follows. category: ethers-buliding-blocks

Intermediate Example Int 10.22.011 -bromo-5-f luoro-2-methoxy-4-(methy Isu Ifany l)benzeneTo a stirred solution of sodium methanethiolate (0.47 g) in DMF (15 mL) at 0 C was added 1 -bromo-4,5-difluoro-2-methoxybenzene (1 .5 g). The mixture was stirred at r.t. for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 1 .46 g of the title compound.

According to the analysis of related databases, 202865-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; SCHIROK, Hartmut; BRIEM, Hans; WO2012/143329; (2012); A1;,
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Reference of 10075-63-5,Some common heterocyclic compound, 10075-63-5, name is 1,5-Dimethoxynaphthalene, molecular formula is C12H12O2, 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.

9.5 g of Intermediate 1-1 was dissolved in 150 ml of acetonitrile, and 8.9 g of N-bromosuccinimide was slowly dropwise added thereto at 0 C. for 10 minutes. The reaction mixture was slowly heated from 0 C. to ambient temperature for 4 hours, and the reaction was terminated by adding water. The reaction mixture was distilled under a reduced pressure, and the residue was subjected to extraction three times using ethyl acetate. The resultant was dried using anhydrous magnesium sulfate and distilled under a reduced pressure, and the residue was separately purified using silica gel column chromatography to obtain 12.9 g of Intermediate 1-2 (Yield: 93%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; Samsung Display Co., Ltd.; Kim, Jong Woo; Kim, Young Guk; Im, Jin Oh; Hwang, Suk Hwan; Kim, Hyung Guen; (58 pag.)KR2015/104678; (2015); A;,
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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. 239122-51-1, name is 5-Bromo-3-fluoro-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 239122-51-1

Preparation of 3-amino-5-fluoro-4-methoxybenzonitrile[00165] A mixture of 5-bromo-3-fluoro-2-methoxyaniline (500 mg, 2.27 mmol), potassium ferrocyanide (II) hydrate (240 mg, 0.57 mmol), sodium carbonate (241 mg, 2.27 mmol) and palladium(II) acetate (25.5 mg, 0.11 mmol) in DMA (2 mL) was purged with nitrogen and heated at 120 0C for 6 hours. The reaction mixture was diluted with ethyl acetate (20 mL) and filtered through CELITE. The filtrate was washed with water (20 mL), 5% NH4OH (10 mL), dried over MgSO4, filtered and concentrated to isolate Intermediate 25 (213 mg, 56.4 % yield). HPLC: Rt = 0.73 min. (PHENOMENEX Luna 5 micron C18 4.6 x 30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate = 5 mL/min., detection at 254 nm). MS (ES): m/z = 167.2 [M+H]+. Intermediate 25 was used in the synthesis of Examples 234 and 239.

The synthetic route of 239122-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FINK, Brian; CHEN, Libing; GAVAI, Ashvinikumar; HE, Liqi; KIM, Soong-Hoon; NATION, Andrew; ZHAO, Yufen; ZHANG, Litai; WO2010/42699; (2010); 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. 1236000-51-3, name is N-Methyl-1-(4-(trifluoromethoxy)phenyl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H11ClF3NO

Intermediate 26 {[5-(4-bromophenyl)-2-thienyl]methyl}methyl({4[(trifluoromethyl)oxy]phenyl}methyl)amine (1-[5-(4-bromophenyl)-2-thienyl]-N-methyI-N-({4-[(trifluoromethyl)oxy]phenyl}methyl)methanamine). To a solution of 0.3 g of Intermediate 25 and 0.26 g of Intermediate 1 in 8.5 ml of DCE under N2 atmosphere were added dropwise 0.226 ml of Et3N and 0.342 g of NaHB(AcO)3 consecutively. The mixture was stirred overnight at room temperature and 1 N NaOH was added. The resulting mixture was extracted with CH2CI2, the combined organic layers were dried over Na2SO4, filtered and concentrated to dryness. The crude was purified by chromatography on silica gel eluting with EtOAc-Hex 0:100 to 10:90 to afford 0.383 g of the desired compound with 10% of the starting aldehyde. This mixture was re-purified on silica gel eluting with EtOAc-Hex 0:100 to 10:90 to afford 0.348 g (67%) of the title compound as a colourless oil.1H NMR (delta, ppm, CDCI3): 7.47 (dd, 4H); 7.42 (d, 2H); 7.18 (d, 2H); 7.15 (d, 1 H); 6.90 (d, 1 H); 3.75 (s, 2H); 3.58 (s, 2H); 2.28 (s, 3H). [ES MS] m/z: 456 (MH+).

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; GLAXO GROUP LIMITED; BUENO-CALDERON, Jose Maria; FERNANDEZ-MOLINA, Jorge; LEON-DIAZ, Maria Luisa; MALLO-RUBIO, Araceli; MANZANO-CHINCHON, M Pilar; WO2010/81904; (2010); 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. 57602-02-5, name is 1,14-Dibromo-3,6,9,12-tetraoxatetradecane, A new synthetic method of this compound is introduced below., Safety of 1,14-Dibromo-3,6,9,12-tetraoxatetradecane

General procedure: Thioacetate 3 (2.2 eq) and dibromide (1eq) were dissolved in dry DMF. DEA was added dropwise and the reaction was stirred for 3 h at room temperature. Then the reaction mixture was washed with 1 M HCl (aq), extracted with CH 2Cl 2, dried with Na 2SO 4. The solution was concentrated and purified by column chromatography.

The synthetic route of 57602-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Yang; He, Yun; Li, Xingzhe; Dinh, Hieu; Iyer, Suri S.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 636 – 643;,
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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. 121588-79-2, name is trans-4-Methoxycyclohexanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H15NO

Example 660: 2-[3-(5-chloro-2-{[trans-4-methoxycyclohexyl]amino}pyrimidin-4-yl)-5-oxo- 5H,6H,7H-pyrrolo[3,4-b]pyridin-6-yl]-N-[(1S)-2-hydroxy-1-(3-methylphenyl)ethyl]acetamide (3567) DIPEA (59.9 muIota, 0.343 mmol) was added to a stirred solution of (S)-2-(3-(2,5-dichloropyrimidin- 4-yl)-5-oxo-5H-pyrrolo[3^-b]pyridin-6(7H)-yl)-N-(2-hydroxy-1-(m-tolyl)ethyl)acetarnide (80 mg, 0.137 mmol) and (1 r,4r)-4-methoxycyclohexanamine (26.6 mg, 0.206 mmol) in dioxane (1 mL) under nitrogen. The mixture was heated to 90 C and stirred for 16 h. The mixture was allowed to cool to room temperature and was diluted with EtOAc (20 mL) and water (20 mL). The phases were separated and the aqueous layer was extracted with EtOAc (2 x 20 mL). The combined organic extracts were washed with brine (60 mL), dried (MgS0 ) and concentrated. The crude product was purified by chromatography (SiO2, 24 g column, 0-10% MeOH in DCM) to afford a beige solid. The product was loaded onto a column packed with SCX (0.5 g) in MeOH. The column was washed with MeOH and the product eluted with 0.7 M ammonia in MeOH. The resulting mixture was concentrated in vacuo to afford the title compound (52 mg, 66.4 %) as a beige solid. 1 H NMR (DMSO-d6, 400 MHz) delta 9.09 (1 H, s), 8.54 (1 H, d), 8.48 (1 H, s (br)), 8.40 (1 H, d), 7.62 (1 H, s (br)), 7.21 (1 H, t), 7.15 – 7.08 (2H, m), 7.07 – 7.03 (1 H, m), 4.91 (1 H, t), 4.88 – 4.80 (1 H, m), 4.64 (2H, s), 4.34 (1 H, d), 4.29 (1 H, d), 3.77 – 3.62 (1 H, m), 3.61 – 3.50 (2H, m), 3.22 (3H, s), 3.17 – 3.05 (1 H, m), 2.29 (3H, s), 2.10 – 1.84 (4H, m), 1.41 – 1.24 (2H, m), 1.24 – 1.11 (2H, m). LCMS: [M+H]+ = 565.

According to the analysis of related databases, 121588-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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Synthetic Route of 2186-92-7, 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. 2186-92-7, name is P-anisaldehyde dimethyl acetal belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2) Synthesis of [6-Methoxy-3,4,5-Tris(4-Methoxy-Benzyloxy)Tetrahydropyran-2-yl]Methanol of Formula (V)a) Step 1: Synthesis of 6-methoxy-2-(4-methoxyphenyl)-hexahydropyrano[3,2-D][1,3]dioxine-7,8-diol of formula (VII)The synthesis begins with the protection of the primary alcohol (VIII) (3,4,5-trihydroxy-6-methoxytetrahydro-pyran-2-ylmethanol) in the form of an acetal (VII) (6-methoxy-2-(4-methoxyphenyl)hexahydropyrano[3,2-D]-[1,3]dioxine-7,8-diol) through the action of p-anisaldehyde dimethyl acetal (III) in the presence of camphorsulfonic acid in DMF (dimethylformamide).The reaction is carried out at ambient temperature under an industrial vacuum (pressure=40 mbar) (evaporation of the methanol form) for 2 hours, so that a significant advancement in the formation of the desired product is observed, such that only traces of the starting product remain.After an aqueous treatment in a basic medium, the traces of starting product are eliminated by washing with cyclohexane; this makes it possible to isolate the compound (VII) in the form of a white solid with yields of between 60% and 80%

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, P-anisaldehyde dimethyl acetal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vachy, Robert; US2011/136748; (2011); A1;,
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Application of 6850-60-8, These common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, 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 18 (75 mg, 0.25 mmol) in 5 mL EtOH in sealed tubewas added various anilines or benzylamines, the mixture was stirred at150 C. After completion, the reaction was cooled to room temperature.In the cases of solid precipitation in the reaction, the precipitates werecollected by filtration, washed with cold EtOH and dried to afford thefinal products. When no solid precipitated in the reaction, the solventwas removed in vacuo and then purified by flash column chromatographyto afford the final products.

Statistics shows that (4-Ethoxyphenyl)methanamine is playing an increasingly important role. we look forward to future research findings about 6850-60-8.

Reference:
Article; Li, Wenlong; Yin, Ying; Shuai, Wen; Xu, Feijie; Yao, Hong; Liu, Jie; Cheng, Keguang; Xu, Jinyi; Zhu, Zheying; Xu, Shengtao; Bioorganic Chemistry; vol. 83; (2019); p. 380 – 390;,
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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 121588-79-2 as follows. Recommanded Product: trans-4-Methoxycyclohexanamine

General procedure: To a suspension of 9 (26.6 g, 76.3 mmol) in N,N-dimethylformamide (380 mL) was added 1-amino-2-methyl-propan-2-ol (8.16 g, 91.5 mmol) and triethylamine (31.9 mL, 228 mmol) at 0 C. The reaction mixture was stirred at room temperature for 5.5 h. Then the reaction mixture was diluted with cold water (1000 mL) and the mixture was stirred at room temperature for 1 h. The resulting precipitate was collected and washed with water. The precipitate was triturated with a mixture of diethyl ether and diisopropyl ether (1:1, 60 mL) to give the title compound (27.7 g, 83%) as a tan colored powder.

According to the analysis of related databases, 121588-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koizumi; Tanaka, Yoshihito; Matsumura, Takehiko; Kadoh, Yoichi; Miyoshi, Haruko; Hongu, Mitsuya; Takedomi, Kei; Kotera, Jun; Sasaki, Takashi; Taniguchi, Hiroyuki; Watanabe, Yumi; Takakuwa; Kojima, Koki; Baba, Nobuyuki; Nakamura, Itsuko; Kawanishi, Eiji; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3440 – 3450;,
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Application of 4457-67-4, A common heterocyclic compound, 4457-67-4, name is 1-Bromo-4-methoxybutane, molecular formula is C5H11BrO, 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.

c) 2-(4-Methoxybutoxy)-terephthalic acid dimethyl ester Alkylation of 2-hydroxy-terephthalic acid dimethyl ester (10 g) with 4-methoxybutyl bromide in anhydrous acetone in the presence of dried potassium carbonate and potassium iodide in a manner analogous to that described in Example 16a) yields the title compound, Rf (B)=0.20, in the form of a slightly yellowish oil.

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; Ciba-Geigy Corporation; US5641778; (1997); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem