Author: Jessica.F

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. 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, A new synthetic method of this compound is introduced below., Product Details of 204452-91-5

[0578] Into a 3 I 4-necked round-bottom flask was placed7 -( dimethoxymethyl)-1 ,2,3,4-tetrahydro-1 ,8-naphthyridine(intermediate 4, 114.6 g, 550.3 mmol) in acetonitrile (2 1).This was followed by the addition of NBS (1 03 g, 578 mol) inportions with stirring at 25 C. The resulting solution wasstirred for 30 min at 25 C. The resulting mixture was concentratedunder vacuum and the residue was diluted with1000 ml of diethylether. The mixture was washed with 3xl 00ml of ice/water. The aqueous phase was extracted with 2xl 00ml of diethylether and the organic layers were combined. Theresulting mixture was washed with lxlOO ml of brine, driedover sodium sulfate and concentrated under vacuum to givethe title compound as a light yellow solid. LC-MS: (ES, m/z):[0579] 286.03 [M+Ht. 1H-NMR: (300 MHz, CDCI3 ) o1.86-1.94 (2H, m), 2.70-2.74 (2H, m), 3.9-3.43 (2H, m), 3.47(6H, s), 5.23 (lH, s), 5.58 (lH, s), 7.29 (lH, s).

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; Novartis AG; Buschmann, Nicole; Fairhurst, Robin Alec; Furet, Pascal; Knoepfel, Thomas; Leblanc, Catherine; Liao, Lv; Mah, Robert; Nimsgern, Pierre; Ripoche, Sebastien; Xiong, Jing; Han, Bo; Wang, Can; Zhao, Xianglin; US2015/119385; (2015); A1;,
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Reference of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 asolution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (e, 1.0 g 3.52 mmol) in ethanol (20 mL) was addedsubstituted aromatic amine (3.52 mmol) and acetic acid (1 drop). Themixture was refluxed for 3 h. Thereafter, the mixture was cooled toroom temperature, the precipitate was formed and filtered, washedwith ethanol and dried under reduced pressure to afford product l1-l14

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Article; Chen, Shaowei; Han, Yufei; Hou, Yunlei; Wang, Ruxin; Yan, Pingzhen; Ye, Tianyu; Zhao, Yanfang; Bioorganic Chemistry; vol. 99; (2020);,
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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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., Safety of Perfluoro(2-methyl-3-oxahexanoyl) fluoride

Into a flask under a nitrogen gas atmosphere, 26 g of the compound (62) and 100 g of R225 were introduced. With cooling with ice, 91 g of the compound represented by Rf2-C(O)F was dropwise added thereto while stirring inside of the flask. Inside of the flask was further stirred, and then, the content was concentrated and filtrated to obtain 88 g of compound (52).

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; Asahi Glass Company, Limited; EP2039672; (2009); A1;,
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Related Products of 332-48-9, A common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

EXAMPLE 103 4-Benzyl-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride STR139 From a mixture of 4-benzylpiperidine (500 mg, 2.85 mmol), 2-(4-fluorophenoxy)ethyl bromide (655 mg, 2.99 mmol) and K2 CO3 (413 mg, 2.99 mmol) in CH3 CN (20 mL) was obtained the title compound as a fluffy, colorless, crystalline solid (395 g, 79%): mp 165-167 C., 1 H NMR (CDCl3) 1.70-1.90 (m, 3H), 1.94-2.14 (m, 2H), 2.59 (d, J=7.2 Hz, 2H), 2.65-2.85 (m, 2H), 3.20-3.50 (m, 2H), 3.65 (d, J=12 Hz, 2H), 4.49 (t, J=4.5 Hz, 2H), 6.76-7.30 (m, 9H), 12.47 (bs, 1H); Anal. Calcd for C20 H25 ClFNO: C, 68.66; H, 7.20; N, 4.00. Found: C, 68.66; H, 7.11; N, 3.98.

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; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); A;,
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These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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: 702-24-9

To a solution of 2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethyl methanesulfonate (1.65 g, 4.44 mmol, Intermediate AO), 1-(4-methoxyphenyl)-N-methyl-methanamine (671 mg, 4.44 mmol) in DMF (20.0 mL) was added K2CO3 (1.23 g, 8.88 mmol). The mixture was stirred at 20 C. for 15 hours. On completion, the mixture was diluted with H2O (60 mL), then extracted with EA (3¡Á30 mL). The organic layers were washed with brine (3¡Á30 mL) and dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The mixture was purified by reverse phase: (0.1% FA) to give the title compound (700 mg, 36% yield) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 8.52 (s, 1H), 7.33 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 3.87 (s, 2H), 3.83 (s, 3H), 3.81-3.75 (m, 2H), 3.68-3.61 (m, 8H), 3.56-3.48 (m, 2H), 3.38-3.25 (m, 2H), 2.96-2.84 (m, 2H), 2.48 (s, 3H), 1.46 (s, 9H).

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

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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Electric Literature of 592-55-2, These common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, 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. 2-Ethoxyethoxynitrobenzene 2-Nitrophenol (91.0 g., 0.65 mole), 2-bromoethyl ethyl ether (100.0 g., 0.65 mole), anhydrous potassium carbonate (9.0 g, 0.72 mole) and acetone (1 liter) were refluxed for 65 hours. The reaction mixture was filtered, and the acetone removed by rotary evaporation. The residue was partitioned between 200 ml. of dichloromethane and 100 ml water. The organic phase was further washed with 200 ml. of 10% sodium hydroxide followed by 100 cc of water. The product (58.0 g) was obtained in 42% yield by a vacuum distillation (100-120 C./0.5 mm).

Statistics shows that 1-Bromo-2-ethoxyethane is playing an increasingly important role. we look forward to future research findings about 592-55-2.

Reference:
Patent; GAF Corporation; US4203901; (1980); A;,
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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. 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H9F2NO2

To a stirred solution of 2,6-difluoro-3,5-dimethoxyaniline (0.4g, 2.11 mmol) and 6-chloro nicotinaldehyde (0.44g, 3.17 mmol) in toluene (20mL) was added catalytic PTSA and molecular sieves (0.4 g). Heated the reaction mass to reflux in a Dean Stark apparatus for overnight. Concentrated the reaction mass and diluted the residue with methanol, cooled to 0 C and added sodium borohydride (0.3g, 8.4 mmol). Stirred the reaction mass at room temperature for lh and further heated to 70 C for lh. Quenched the reaction mass with ice cold water, warmed to room temperature and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (3x30mL). The organic phase was washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The crude material was purified by silica column chromatography to afford desired title compound (0.2g, 30%) as a solid. LCMS: m/z = 315.1 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 651734-54-2.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
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Reference of 886762-08-9, 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 886762-08-9 as follows.

General procedure: To a stirred solution of 5-bromo-2-(trifluoromethoxy)aniline (540 mg, 2.11 mmol) in pyridine was added pyridine-2-sulfonylchloride (410 mg, 2.31 mmol and the mixture was heated to 45C for 4 h. After quenchingwith water the mixture was extracted with CH2C12, dried over MgSO4 and evaporated togive a solid (769 mg) that was used without further purification. To a mixture of the aforementioned crude solid and (chloromethoxy)ethane (329 mg, 3.49 mmol) in DMF at room temperature was added a 60% w/w dispersion of Nail in mineral oil (140 mg, 3.49 mol) and the mixture was stirred for 1 h. After quenching with water the mixture was extracted with CH2CI2, dried with MgSO4 and evaporated to give a solid which waspurified by column chromatography eluting with hexanes/EtOAc 3:1. The title compound was isolated as a colourless oil (857 mg, 89%, 2 steps).?H NMR [400 MHz, CDCI3I 6 8.75 (ddd, J =4.8, 1.6, 1.0 Hz, 1H), 7.90-7.82 (m, 2 H), 7.54-7.46 (m, 3 H), 7.10 (dddd, J = 8.9, 1.9,1.8, 1.8 Hz, 1 H), 5.21 (br s, 2 H), 3.79 (q, J = 7.0 Hz, 2 Fl), 1.20 (t, J = 7.0 Hz, 3 H). LRMS (APCI?) calcd for C13H10BrF3N2O3S 409 (M-EtO), found 409.

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H13NO

A solution of (3-methoxy-benzyl)-methyl-amine (0.590 g, 3.93 mmol) and TEA (1.1 ml_) in DCM (5 mL) was treated with 2-bromo-1-thiophen-3-yl-ethanone (1.11 g, 5.11 mmol). After 16 h at 23 0C, the mixture was poured onto water and extracted with DCM. The organic layer was collected, dried (Na2SO4), and concentrated to give the desired product (1.149 g, >100% crude). 1H NMR (CDCI3): 8.24 (ddLambda J = 2.9,’ 1.2, 1 H), 7.57 (dd, J = 5.1 , 1.2, 1 H), 7.28 (dd, J = 5.1 , 2.9, 1 H), 7.26-7.21 (m, 1 H), 6.94-6.90 (m, 2H), 6.83-6.79 (m, 1 H), 3.79 (s, 3H), 3.65 (s, 2H), 3.64 (s, 2H), 2.37 (s, 3H).

According to the analysis of related databases, 41789-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/66197; (2006); A1;,
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Synthetic Route of 1159512-64-7, 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 1159512-64-7 as follows.

(a) 4-bromo-2-fluoro-3-(trifluoromethoxy)aniline To a solution of 2-fluoro-3-(trifluoromethoxy)aniline (1.0 g, 5.13 mmol) dissolved in DMF (2 mL) at 0 C. was slowly added a solution of cold N-bromosuccinimide (0.91 g, 5.13 mmol) dissolved in DMF (6 mL) over 5 min. The reaction mixture was stirred at 0 C. for 1 h, extracted with EtOAc (125 mL) and washed with water (3*25 mL). The combined aqueous layers were extracted with EtOAc (75 mL). The combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated to produce the title compound as a dark colored liquid (1.27 g, 90% yield). (m/z): [M+H]+ calcd for C7H4BrF4NO 273.94. found 273.8.

According to the analysis of related databases, 1159512-64-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
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