Month: March 2021

Application of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-(5-amino-4-fluoro-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (1.36 g, 4.28 mmol, 1.00 eq), 4-methoxy-N-methylbenzylamine (0.971 g, 6.42 mmol, 1.50 eq) and DBU (0.960 mL, 6.42 mmol, 1.50 eq) were combined in NMP (20 mL) and heated at 180¡ã C. under Ar overnight. The mixture was cooled to RT and poured onto H2O (200 mL). The resulting solids were collected by filtration, rinsed very well with H2O, dried on the filter to dampness and then dissolved in EtOAc. The solution was dried (MgSO4), filtered and evaporated to afford 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (1.86 g, 100percent yield) as a brittle brown foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): delta 8.45 (s, 1H), 7.63 (s, 1H), 7.16 (d, J=8.8 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 6.86-6.82 (m, 1H), 6.57 (d, J=9.6 Hz, 1H), 6.29 (s, 1H), 4.88 (br s, 2H), 4.85 (s, 2H), 3.69 (s, 3H), 3.52 (s, 3H), 3.07 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 433.3 [M+H]+.

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

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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. Recommanded Product: 588-63-6

Intermediate 110 1,1-Dimethylethyl (2/?,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-({[3-(phenyloxy)propyl]oxy} methyl)- 1 -pyrrolidinecarboxylate1 ,1-Dimethylethyl (2R,4S)-4-{[(1 ,1-dimethylethyl)(dimethyl)silyl]oxy}-2-(hydroxymethyl)-1- pyrrolidinecarboxylate (0.6 g, 1.810 mmol) was diluted in THF (1 ml) to give a colorless solution. The resulting mixture was cooled down to 0 0C under argon. Then sodium hydride (0.217 g, 9.05 mmol) in THF (2ml_) was added to give a white suspension followed by [(3-bromopropyl)oxy]benzene 3-bromopropyl phenyl ether (0.779 g, 3.62 mmol) in THF (1 ml). The resulting mixture was stirred at rt over the week end (96 h).The reaction was then quenched by addition of water at 0 0C. The THF was removed in vacuo and the resulting crude was diluted in DCM and washed with 0.1 M HCI, sat NaHCOs using a hydrophobic frit. The organic layer was then concentrated in vacuo to yield a colorless oil. This resulting oil was loaded onto a 5 g silica SPE cartridge, then eluted sequentially with hexane DCM and EA. The corresponding fractions were combined and evaporated to afford the title compound (0.45 g, 53percent). LC-MS: m/z, 466 (M+H), rt 1.67 min.

The synthetic route of (3-Bromopropoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/26197; (2009); A1;,
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Synthetic Route of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

(Formula 1-2: methyl 4-(((3-(trifluoromethoxy)phenyl)amino)methyl)benzoate)[1723][1724]Compound ofFormula 1-1(3-(trifluoromethoxy)aniline; 0.385 mL, 4.625 mmol), methyl 4-(bromomethyl)benzoate (1.271 g, 5.550 mmol) and DIPEA (1.228 mL, 6.937 mmol) were dissolved in acetonitrile (5 mL) at room temperature and stirred at the same temperature for 16 hours. Water was poured into the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=20percent) to give the desired compound ofFormula 1-2(0.607 g, 40.3percent) in the form of a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Trifluoromethoxyaniline, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Changsik; YANG, Hyun-Mo; CHOI, Hojin; KIM, Dohoon; KIM, Soyoung; HA, Nina; LIM, Hyojin; KO, Eunhee; YOON, Seongae; BAE, Daekwon; WO2014/178606; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4179-19-5, name is 3,5-Dimethoxytoluene, 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 4179-19-5, Safety of 3,5-Dimethoxytoluene

Step 1: Put 1,3-dimethoxy-5-methylbenzene (30g, 0.20mol)And dichloromethane (900 mL) were added to a dry round bottom flask (1 L), and the above solution was added dropwise with dichlorosulfone (52.5 g, 0.40 mol) under ice-cooling,After the addition was complete, the mixture was stirred at room temperature overnight.After completion of the reaction, aqueous NaHCO3 solution was added dropwise to adjust the pH = 8, and dichloromethane was extracted.Wash with dilute hydrochloric acid and distilled water,Dry and concentrate under reduced pressure to obtain compound 2,4-dichloro-1,5-dimethoxy-3-methylbenzene(31g, white solid),Used directly in the next step.

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; Rudong Lingda Bio-pharmaceutical Technology Co., Ltd.; Wan Huixin; Pan Jianfeng; Ma Jingui; (63 pag.)CN110857300; (2020); A;,
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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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., SDS of cas: 6298-96-0

To a 250 mL RBF was added (S)-1-(4-methoxyphenyl)ethanamine (5.65 ml, 38.1 mmol 1.0 equiv.), 1-(pyridin-2-yl)ethanone (4.49 ml, 40 mmol, 1.05 equiv.), DCE (Volume: 38.1 ml, 1.0M) and STAB-H (16.15 g, 76 mmol, 2.0 equiv.) at rt and the reaction was stirred for 24h. The reaction was quenched by the addition of 1N NaOH until a pH of 8 was achieved. The phases were separated and the organic layer was treated with 1N NaOH until pH 11 was observed. The DCM layer was dried with MgSO4, filtered and concentrated to an oily residue. The residue was purified via combiflash to separate the diastereomers (~4:1 by crude NMR, 80g column 10-30% EtOAc in hexanes over 40 min). The fractions were concentrated to a clear oil which solidified upon standing. (S)-1-(4-methoxyphenyl)-N-((S)-1-(pyridin-2- yl)ethyl)ethanamine (3.86 g, 15.06 mmol, 40 % yield). 1H NMR (400 MHz, CDCl3): delta = 8.60 (d, J= 5.2 Hz, 1H), 7.61 (dt, J= 7.6, 1.8 Hz, 1H), 7.21-7.12 (m, 1H), 7.13 (d, J= 9.2 Hz, 2H), 7.06 (d, J= 7.2 Hz 1H), 3.80 (s, 3H), 3.57 (q, J= 7.4 Hz, 1H), 3.39 (q, J= 6.9 Hz, 1H), 1.29 (d, J= 6.8 Hz, 3H), 1.26 (d, J= 7.3 Hz, 3H); LC/MS 75% MeOH in H2O over 3 minutes, rt = 0.480 at 254 nM, MS (+) 257.2

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; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
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Electric Literature of 17715-69-4,Some common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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 mixture of magnesium turnings (1.2 g, 49.4 mmol) etched with iodine in anhydrous tetrahydrofuran (4 mL) at reflux was added 1-bromo-2,4-dimethyoxybenzene (6.0 mL, 41.7 mmol) dropwise over 10 min. The reaction mixture was heated at reflux for 30 min, and then cooled to ambient temperature. The prepared grignard reagent was added to a mixture of tetrahydro-4-[[4-[3-(methoxymethyl-amino)-3-oxopropoxy]phenyl]sulfonyl]-2H-pyran-4-carboxylic acid, 1,1-dimethylethyl ester (1.0 g, 1.9 mmol, prepared as in Example 7) in anhydrous THF (10 mL) at 0¡ã C. The reaction mixture was warmed to ambient temperature, and, after 2 hr, was quenched with saturated ammonium chloride, and then partitioned between ethyl acetate and water. The layers were separated, and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was covered with diethylether. The resulting green solid was triturated with diethyl ether. The final solid was collected to afford 2.2 g (94percent) of the desired ketone as a pale green powder. ESMS m/z=585 [M+Na]+. HRMS calculated for C29H38NO9S: 563.2315 [M+H]+, found: 563.2319.

The synthetic route of 17715-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Freskos, John N.; Fobian, Yvette M.; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Carroll, Jeffery N.; DeCrescenzo, Gary A.; Hockerman, Susan L.; Kassab, Darren J.; Kolodziej, Steve A.; McDonald, Joseph; Mischke, Deborah A.; Norton, Monica B.; Rico, Joseph G.; Talley, John J.; Villamil, Clara I.; Wang, Lijuan Jane; US2004/10019; (2004); 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H10O2

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 ¡Á 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (3 mL) in a compound 7b (76.7 mg, 300 mumol), -3,5- dimethoxybenzene (121 mg 1-ethynyl, 750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. Using ascorbate (60.0 mg, 300 mumol) was prepared in the desired compound. The reaction mixture was stirred at room temperature for 48 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 20: 1 CH2Cl2 / MeOH) Compound 2b was obtained by using as a brown solid (90.6mg, 73%).

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; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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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 52189-63-6 as follows. Application In Synthesis of 1-Fluoro-3,5-dimethoxybenzene

EXAMPLE 12 Method of Forming a 1-(2,6-dimethoxy-4-fluorophenyl)-2-methylpropan-1-one Intermediate to a Photoinitiator of the Present Invention The following reaction was carried out as detailed below: Into a 1-liter, three-necked round-bottom flask was placed 20.0 g (0.13 mole) of 1,3-dimethoxy-5-fluorobenzene, 13.6 g (0.0.13 mole) of 2-methylpropanoyl chloride, and 100 ml of nitrobenzene. The mixture was flushed with argon and an equal molar amount of AlCl3 (17.2 g) was added to the reaction mixture while stirring at 5C. The mixture was stirred at a temperature of 5C for about 1 hour after the addition of the AlCl3. The reaction mixture was then mixed with about 100 ml of distilled water and extracted with dichloromethane. The organic layer was washed with NaHCO3 solution, salt water, and then dried. The solvent was removed by vacuum to yield the final productproduct, 1-(2,6-dimethoxy-4-fluorophenyl)-2-methylpropan-1-one. The yield of the reaction was 22.8 g of product (77%).

According to the analysis of related databases, 52189-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIMBERLY-CLARK WORLDWIDE, INC.; EP1117698; (2006); B1;,
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Related Products of 171290-52-1, These common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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.

In a 25 ml round bottom flask, 9 mg of copper acetate,18mg 1,10-phenanthroline, 276mg potassium carbonate, 325mgN-allyl-N- (6-chlorohexynyl) p-toluenesulfonamide, 486mg of 3,5-dimethoxyphenylacetylene, 5mL of toluene,Then heated to 100 C for 12h, and then filtered to obtain 6-allyl-7-((3,5-dimethoxyphenyl) ethynyl) -1-p-toluenesulfonyl-2,3,4 Crude product of 5,5-tetrahydro-1H-azepineThe crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 20: 1).Get6-allyl-7-((3,5-dimethoxyphenyl) ethynyl) -1-p-toluenesulfonyl-2,3,4,5-tetrahydro-1H-azepine Pure302 mg, yield 67%.

Statistics shows that 3,5-Dimethoxyphenylacetylene is playing an increasingly important role. we look forward to future research findings about 171290-52-1.

Reference:
Patent; The Chinese People’s Liberation Army National Defense University Of Science And Technology; Yang Xuheng; Huang Jian; Wang Fang; Li Yujiao; Wang Jianfang; Tao Chengan; Zou Xiaorong; Song Chenchao; (30 pag.)CN110627722; (2019); A;,
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Reference of 175278-17-8,Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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 solution of 2-bromo-4-(trifluoromethyloxy)aniline (5.1 g), in 1 ,4-dioxane (30 ml.) was treated with bis(trichloromethyl) carbonate (2.2g). The mixture was heated to 1000C to give a clear solution then allowed to cool to ambient temperature. The solvent was evaporated and the residue was dissolved in dichloromethane (70ml) and 1 ,1- dimethylethyl 4-amino-1 -piperidinecarboxylate (4.0 g) was added. The mixture was stirred overnight at room temperature. Silica gel was added and the solvent was evaporated. The residue was loaded onto a silica gel chromatography column which was eluted with hexane/ethyl acetate 0-100% followed by chromatography on silica gel eluted with dichloromethane/methanol 0-10% to give the title compound as a white solid from diethyl ether (4.3 g).1HNMR delta (DMSO, 400 MHz): 1.25 (2H, m), 1.40 (9H, s), 1.79 (2H, m), 2.93 (2H, broad), 3.64 (1 H, m), 3.80 (2H, m), 7.21 (1 H, d), 7.35 (1 H, d), 7.66 (1 H, s), 7.91 (1 H, s), 8.19 (1 H, d).

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/107565; (2007); A1;,
Ether – Wikipedia,
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