Category: ethers-buliding-blocks

Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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. COA of Formula: C16H19NO2

To a cooled (-35 C) solution of 4-Fluoro-3-nitrobenzenesulfonyl chloride (4.89 g, 20.42 mmol) in THF (50 mL) was added Triethylamine (3.13 mL, 22.46 mmol), followed by addition of Bis-(4-methoxybenzyl)amine (4.97 mL, 20.7 mmol) in THF (50 mL) solution over 30 min. while the temperature was kept at -35 C. After completion of the addition, the temperature was allowed slowly to warm to 0 C over 1 h., and the mixture was stirred at 0 C for an additional hour. The mixture was neutralized with 1 N HC1 to pH about 4-5 and diluted with EtOAc (100 mL). The organic layer was separated, washed with 1 N HC1 (10 mL), 7.5% NaHC03 aqueous solution (20 mL), and brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was treated with DCM (30 mL), and hexane was added to the suspension until it became cloudy. The resulting suspension was sonicated for 2 min. and left at r.t. for 1 h. The mixture was filtered and washed with hexane to afford the desired title product (6.85 g) without further purification. The mother liquid was concentrated under reduced pressure. The residue was treated with DCM (5 mL) and hexane was added as the procedures mentioned above to afford the additional 0.51 g of the title product. Total product 4-fluoro-N,N-bis[(4-methoxyphenyl)methyl]-3-nitro-benzenesulfonamide obtained is 7.36 g (78%). NMR (400 MHz, DMSO-de): d 8.18-8.23 (m, 2 H), 7.75-7.79 (q, 1 H), 7.08 (d, 4 H), 6.81 (d, 4 H), 4.31 (s, 4 H), 3.71 (s, 6 H). 19F NMR (376 MHz, DMSO-d6): d -112.54 (s, 1 F). LCMS calculated for C22H22FN2O6S (M+H)+: m/z = 461.11; found: 461.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17061-62-0, its application will become more common.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; ZHUO, Jincong; LEAL, Raul; SHETTY, Rupa; LUENGO, Juan; COMBS, Andrew, Paul; (525 pag.)WO2020/97577; (2020); A1;,
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Reference of 886762-08-9, The chemical industry reduces the impact on the environment during synthesis 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General Procedure: Methyl 2-{[4-(chlorosulfonyl)-2,3-dimethylphenyl]oxy}propanoate (7) (4 g, 13.0 mmol) was dissolved in pyridine (10 mL). After 5 min, 3-bromo-2-chloroaniline (3.22 g, 15.6 mmol) was added. The reaction was complete within a few hours. The reaction mixture was then extracted using diethyl ether. The combined organic phases were washed with 1N HCl and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound which was used without further purification.

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Evans, Karen A.; Shearer, Barry G.; Wisnoski, David D.; Shi, Dongchuan; Sparks, Steven M.; Sternbach, Daniel D.; Winegar, Deborah A.; Billin, Andrew N.; Britt, Christy; Way, James M.; Epperly, Andrea H.; Leesnitzer, Lisa M.; Merrihew, Raymond V.; Xu, Robert X.; Lambert, Millard H.; Jin, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 8; (2011); p. 2345 – 2350;,
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Reference of 74654-07-2, The chemical industry reduces the impact on the environment during synthesis 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, I believe this compound will play a more active role in future production and life.

HATU (500 mg, 1.315 mmol) was added to a stirred solution of 3-((4-((tert-butoxycarbonyl)amino)naphthalen-1-yl)oxy)pyridin-2-yl)amino)-5-ethynylbenzoic acid (see Example 52(iii) above; 500 mg, 1.009 mmol), 2-(2-(2-methoxyethoxy)ethoxy)-ethanamine (277 mg, 1.695 mmol) and triethylamine (250 muL, 1.796 mmol) in N,N-dimethylformamide (10 mL). The mixture was stirred at rt for 18 h. The mixture was diluted with EtOAc (50 mL) and washed with water (50 mL), 20% brine (3*50 mL) and saturated brine (50 mL). The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by chromatography on the Companion (40 g column, EtOAc) to afford the sub-title compound (580 mg) as a tan foam. LCMS m/z 641 (M+H)+ (ES+); 639 (M-H)- (ES-)

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, 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Topivert Pharma Limited; Respivert Limited; BAKER, Thomas Matthew; FYFE, Matthew Colin Thor; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; MEGHANI, Premji; RIGBY, Aaron; SAMBROOK-SMITH, Colin; THOM, Stephen Malcolm; US2014/296208; (2014); A1;,
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Electric Literature of 701-56-4, 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. 701-56-4 name is 4-Methoxy-N,N-dimethylaniline, 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: Charged a round bottom flask with N-methylaniline 1 (1.5 mmol), maleimide 2 (1.0 mmol) and K2S2O8 (1.5equiv) in CH3CN (3 mL). The contents were stirred at rt for 6-8 h. After the completion of reaction (as indicated by TLC), it was quenched with water (10 mL) and extracted with ethyl acetate (3 ¡Á 10 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude product, which was purified by silica gel column chromatography using a mixture of EtOAc-hexane (2:8) to give the pure product 3 in excellent yields. The structure of the products was confirmed by comparison of mp and 1H, 13C NMR and MS spectral data with those reported in the literature.1

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

Reference:
Article; Yadav, Arvind K.; Yadav, Lal Dhar S.; Tetrahedron Letters; vol. 57; 13; (2016); p. 1489 – 1491;,
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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. 22483-09-6, name is 2,2-Dimethoxyethanamine, A new synthetic method of this compound is introduced below., Quality Control of 2,2-Dimethoxyethanamine

General procedure: Benzaldehyde derivatives (1500 mg, 13.13 mmol) and Aminoacetaldehyde dimethyl acetal (19.70 mmol) were dissolved in 15 mL of methanol, NaBH(OAc)3 (19.70 mmol) was added at 0 C slowly in 3h. The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was extracted with dicloromethane (DCM, 15 mL) three times, and the combined extracts were washed with 2N KOH, brine and dried over Na2SO4. The solution was filtered and added TEA (39.40 mmol) and TsCl (21.00 mmol) at 0C and stirred at room temperature for 5h. The resulting mixture was extracted with DCM (15 mL) three times. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (PE : EA = 5:1) to give the desired product.

The synthetic route of 22483-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Zeyu; Xiao, Qiong; Yin, Dali; Chinese Chemical Letters; (2019);,
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These common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)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. Formula: C13H20O3

To a solution of compound 13 (57.1 mg, 0.245 mmol) in 2 mL CH3CN, triethylorthobenzotate (170 muL, 0.735 mmol) and camphorsulfonic acid (11.4 mg,0.049 mmol) were added. The mixture was refluxed at 85 C for 4 h afterwhich TLC indicated full conversion and quenched by adding Et3N. The mixture was concentrated and theresidue was re-dissolved in 1 mL pyridine and 0.5 mL Ac2O was added. The mixture was stirred at roomtemperature for 2 h after which TLC indicated full conversion. The mixture was concentrated underreduced pressure. The residue was dissolved in 2 mL CH3OH and 1 M HCl (1.5 mL) was added. Themixture was stirred for 5 min and extracted with CH2Cl2. The combined organic layers were dried overNa2SO4 and concentrated. The residue was purified by column chromatography to afford 14 as light yellowsyrup (79.1 mg, 85percent).

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

Reference:
Article; Wang, Lihao; Fan, Fei; Wu, Haotian; Gao, Lei; Zhang, Ping; Sun, Tiantian; Yang, Chendong; Yu, Guangli; Cai, Chao; Synlett; vol. 29; 20; (2018); p. 2701 – 2706;,
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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 10272-07-8 as follows. Quality Control of 3,5-Dimethoxyaniline

Step 1: 1 -Fluoro-3 ,5-dimethoxybenzene[0360] To a mixture of 3,5-dimethoxybenzenamine (6.12 g, 40.0 mmol) and tetrafluoroboric acid (8% solution, 70 mL) was added dropwise a solution of sodium nitrite (2.84 g, 41.2 mmol) in water (10 mL). After stirring at room temperature for 30 min, the reaction mixture was filtered. The solid was collected and washed with water (2×10 mL) and dried under high vacuum. The resulting red solid was suspended in dry hexane (50 mL) and heated to reflux for 2 hr. The mixture was filtered and the filtrate was concentrated to give the crude product as a yellow oil (3.03 g, Yield: 48.5%). MS (ESI) m/z = 157 [M + H]+.

According to the analysis of related databases, 10272-07-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
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Application of 162705-07-9, These common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, 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: 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.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

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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Electric Literature of 74137-36-3, A common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, molecular formula is C7H6Br2O, 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 1.6 M solution of n-butyllithium in hexane (5.65 mL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5¡ã C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL, 4.52 mmol) was added slowly with the temperature held below 0¡ã C. over a period of 15 min. Stirring was continued for 45 min at -5¡ã C., followed by drop wise addition of a solution of 1,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 0¡ã C. The mixture was stirred for 45 min at -5¡ã C. A solution of iodine chloride (1.83 g, 11.3 mmol) in methylene chloride (20 mL) was added in the described manner and stirring continued for additional 20 min at -5¡ã C. The mixture was warmed to room temperature. Water (50 mL) and toluene (50 mL) were added and the layers were separated. The organic layer was washed with a saturated aqueous solution of Na2S2O3 (2.x.30 mL), water and brine (30 mL). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (100 g, AcOEt/heptane 1:9). 1-Bromo-3-iodo-5-methoxy-benzene (2.12 g, 60percent) was obtained as a yellow oil, which crystallized quickly upon standing.

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; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (2006); A1;,
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Synthetic Route of 93919-56-3, These common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)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.

To a solution of 3,3,3-trifluoropropanoic acid (2.28 g, 17.81 mmol) and N,N-diisopropylethylamine (4.2 g) in N,N-dimethylformamide (25 mL), was added HATU (9.25 g) in portions at 0 C. The mixture was then stirred for 5 min at 0 C, followed by addition of a solution of [4-(trifluoromethoxy)phenyl]methanamine (3.1 g, 16.22 mmol) in N,N- dimethylformamide (25 mL). The reaction was allowed to warm to room temperature and stirred for another 3 h. Water (300 mL) was added, and the mixture was extracted with ethyl acetate (200 mL x 3). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column with ethyl acetate/petroleum ether (1/2) as the eluent to afford the desired product (2.4 g, 49% yield).

Statistics shows that (4-(Trifluoromethoxy)phenyl)methanamine is playing an increasingly important role. we look forward to future research findings about 93919-56-3.

Reference:
Patent; INVENTISBIO INC.; DAI, Xing; WANG, Yaolin; (187 pag.)WO2017/139414; (2017); A1;,
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