Month: September 2021

Electric Literature of 2752-17-2, 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 2752-17-2 as follows.

Compounds 1 and 2 were prepared by the following procedure: 2-(4-chloro-3-nitrophenyl)-2-oxoethyl 2-aminobenzoate or 2-(4-amino-3-nitrophenyl)-2-oxoethyl 2-aminobenzoate (44.8 mmol) was suspended in polyphosphoric acid (167.3 g). The reaction mixture was heated to 100 C and stirred for 90 min. The mixture was then poured into H2O/crushed ice (700 ml). The precipitated product was filtered, washed with H2O, dried and recrystallized from 2-methoxyethanol. Compounds 3-17 were prepared by the following general procedure: quinolinone 1 (200 mg, 0.63 mmol) was added to a solution of amine (6.3 mmol) and N-methylpyrrolidone (1.0 ml) and the mixture was stirred at 110 C for 2 h. After cooling to room temperature, H2O (20 ml) was added and the pH adjusted to 7 with dilute HCl (1:3). The precipitated solid was collected by suction, washed thoroughly with H2O and dried at 80 C. The crude product was recrystallized from 2-methoxyethanol.

According to the analysis of related databases, 2752-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Motyka, Kamil; Hlava?, Jan; Soural, Miroslav; Hradil, Pavel; Krej?i, Petr; Kvapil, Lubomir; Weiss, Milo?; Tetrahedron Letters; vol. 52; 6; (2011); p. 715 – 717;,
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Application of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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.

[000214] To a stirred solution of 6 (40 mg, 0.14 mmol) in DMF (3 mL) under argon atmosphere was added CDI (71.7 mg, 0.17 mmol) at 0 C; warmed to RT and stirred for 2 h. To this were added (4-(trifluoromethoxy) phenyl) methanamine 172 (33.8 mg, 0.17 mmol), and diisopropyl ethyl amine (0.05 mL, 0.29 mmol) and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mass was diluted with water (15 mL) and stirred for 1 h. The precipitate was filtered or extracted with EtOAc or CH2C12 and the obtained solid was dried in vacuo or purified by column chromatography or triturated to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-(Trifluoromethoxy)phenyl)methanamine, its application will become more common.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
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Application of 171290-52-1, The chemical industry reduces the impact on the environment during synthesis 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, I believe this compound will play a more active role in future production and life.

(S) -3- (5-amino-3-bromo-4-cyano-1H -Pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7c (5g, 14.1mmol), cuprous iodide (0.6g, 2.8mmol), triethylamine (9mL), [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride (2g, 2.8mmol) And N, N-dimethylformamide (150mL) were heated to 80 C under the protection of argon, and 1-ethynyl-3,5-dimethoxybenzene (14g, 84.5mmol) was added in portions. And stir for 2 hours.After cooling to room temperature, the reaction solution was poured into water and extracted with ethyl acetate (200 mL × 3).The organic phases were combined, dried over anhydrous sodium sulfate, filtered to remove the drying agent, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 5/1) to obtain the target product (S) -3- ( 5-amino-4-cyano-3-((3,5-dimethoxyphenyl) ethynyl) -1H-pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7d (5 g, brown oil), yield: 81%.

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, 3,5-Dimethoxyphenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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. HPLC of Formula: C6H15NO2

[00114] To a glass reactor was charged 3,5-dichlorobenzaldehyde. Absolute ethanol was added to the batch slowly (this addition is mildly exothermic) and agitation started. 2,2- Diethoxyethylamine (1.03 equiv) was slowly added to the batch, keeping the batch temperature at 20-78 C. The batch was then heated to 76-78 C for 2 h. GC-MS analysis indicated reactioncompletion (starting material < 1%). The batch was cooled to ambient temperature for work-up. The batch was concentrated in vacuo to a residue and azeotroped with heptanes (x2). The residue was cooled and held at 0-5 C for 12 h to form a suspension. The solids were collected by filtration and the cake was washed with cold (0-5 C) heptanes, and dried under hot nitrogen (45-5 0 C) to afford Compound 2? as a white solid (94% yield). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common. Reference:
Patent; SARCODE BIOSCIENCE INC.; ZELLER, James, Robert; VENKATRAMAN, Sripathy; BROT, Elisabeth, C.A.; IYER, Subashree; HALL, Michael; WO2014/18748; (2014); A1;,
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Application of 4316-51-2, A common heterocyclic compound, 4316-51-2, name is 4-Methoxytriphenylamine, molecular formula is C19H17NO, 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.

Boron tribromide was added to a dichloromethane solution of 4-methoxytriphenylamine (formula (6)) while cooling, and the mixture was stirred at room temperature for 3 hours to obtain diphenylaminophenol (formula (7) in a yield of 90% It was.

The synthetic route of 4316-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YOKOHAMA NATIONAL UNIVERSITY; NAKAGAWA, TETSUYA; YOKOYAMA, YASUSHI; MIYASAKA, YOSUKE; (14 pag.)JP2018/20988; (2018); A;,
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Reference of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)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.

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Statistics shows that (Trimethoxymethyl)benzene is playing an increasingly important role. we look forward to future research findings about 707-07-3.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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Reference of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-amino-l-brotaunoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10175 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 DL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%) . Rt = 1.75 min (Cond. -MS-Wl) ; 90% homogenity index; LCMS: Anal. CaIc. for [M+H] + C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; BACHAND, Carol; RUEDIGER, Edward H.; KADOW, John F.; WO2010/120621; (2010); A1;,
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Electric Literature of 64465-53-8, 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. 64465-53-8, name is 4-Fluoro-3-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To stirred hydrochloric acid (100 mL) at 0 C. was added 3-methoxy-4-fluoroaniline (10 g, 71 mmol) followed by water (10 mL) and more hydrochloric acid (10 mL). The mixture was warmed to room temperature, stirred for 20 min then cooled to -5 C. A solution of sodium nitrite (5.14 g, 75 mmol) in water (25 mL) was added dropwise such that the internal temperature remained below 0 C. The mixture was warmed to room temperature and stirred for 2 h. The mixture was cooled to -5 C. and a solution of tin(II)chloride dihydrate (64 g, 284 mmol) in hydrochloric acid (200 mL) was added dropwise such that the internal temperature remained below 0 C. The mixture was warmed to room temperature, stirred for 3 h then filtered. The filter cake was washed with hydrochloric acid and dried under vacuum to give a pink solid (7.4 g). The precipitate from the combined filtrates was filtered-off, washed (hydrochloric acid) and dried under vacuum to give a further crop of product (1.8 g. to give a combined yield of 9.2 g, 67%).

The synthetic route of 4-Fluoro-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vernalis Research Limited; US6706750; (2004); B1;,
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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. 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 31576-51-9

In a round bottom flask under nitrogen 150 mg (0.35 mmol) of intermediate Awas dissolved in 5 mL ofCH2Ch and 0.18g of DIPEA (1.4 mmol) was added followed by 125 mg (1.05 mmol) of2-(2-Methoxy-ethoxy)-ethylamine. The mixture was allowed to stirovernight and then condensed in vacuo. The residue was dissolved in 20 mL of EtOAc andwashed with 2x 20 mL of water, 20 mL of brine, dried over Na2S04 and condensed in vacuo.Purification by biotage flash chromatography (Si02, MeOH/CH2Ch/Et3N gradient) affords 99mg of the title compound as a clear oil

The synthetic route of 31576-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZAFGEN, INC.; ZAHLER, Robert; VATH, James, F.; WO2013/169860; (2013); A1;,
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Reference of 2688-84-8, 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. 2688-84-8, name is 2-Phenoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

5.58.1 3-(2-Phenoxyphenylamino)phthalic acid dimethyl ester A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), 2-phenoxyaniline (0.57 g, 3.1 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), rac-BINAP (0.058 g, 0.093 mmol), and cesium carbonate (1.4 g, 4.3 mmol), in 6 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (10 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (30 mL). The filtrate was evaporated, and the residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 0.86 g of the product at 80:20 hexanes-ethyl acetate, in 73% yield: 1H NMR (CDCl3) delta 3.75 (s, 3H), 3.86 (s, 3H), 6.93-7.03 (m, 4H), 7.06-7.12 (m, 2H), 7.17 (dd, J=7.3 Hz, J=1.0 Hz, 1H), 7.29-7.38 (m, 4H), 7.46 (d, J=8.4 Hz, 1H), 7.89 (s, 1H).

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

Reference:
Patent; Muller, George W.; Chen, Roger Shen-Chu; Man, Hon-Wah; Ruchelman, Alexander L.; US2007/49618; (2007); A1;,
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