Month: August 2021

Application of 60792-79-2, The chemical industry reduces the impact on the environment during synthesis 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, I believe this compound will play a more active role in future production and life.

Example 6; Preparation of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(2-((E)-6-(4-hydroxy-6-methoxy-7- methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4- enamido)ethoxy)ethyl)docosa-4,7,10,13,16,19-hexaenamide (I-2); In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min The resulting reaction mixture was stirred at room temperature for 18 h, and then concentrated under reduced pressure. The resulting residue was taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate (850 mg, 74%).tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (1.47 mmol) was then taken up in CH3CN (10 mL) along with mycophenolic acid (470 mg, 1.47 mmol) and EDCI (310 mg, 1.62 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It is then diluted with EtOAc (50 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 620 mg of (E)-tert-butyl 2-(2-(6- (4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4- enamido)ethoxy)ethylcarbamate (83% yield).(E)-tert-Butyl 2-(2-(6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3- dihydroisobenzofuran-5-yl)-4-methylhex-4-enamido)ethoxy)ethylcarbamate (620 mg, 1.22 mmol) was taken up in 10 mL of 4 M HC1 in dioxane and allowed to stir at room temperature for 2 h. The resulting reaction mixture was concentrated under reduced pressure to afford the HCl salt of (E)-N-(2-(2-aminoethoxy)ethyl)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3- dihydroisobenzofuran-5-yl)-4-methylhex-4-enamide This material was taken up in CH3CN (10 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (400 mg, 1.22 mmol), HATU (510 mg, 1.34 mmol) and DIEA (640 muL, 3.66 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. It was then diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (5% MeOH in CH2Cl2) afforded 600 mg of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2- (2-((E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4- methylhex-4-enamido)ethoxy)ethyl)docosa-4,7,10,13,16,19-hexaenamide (68% yield). MS (EI) calcd for C43H60N2O7: 716.44; found 717 (M+1).

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′-Oxybis(ethylamine) dihydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; US2011/213028; (2011); A1;,
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Electric Literature of 6443-69-2, 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. 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 1 (3.6 g, 20 mmol) and NaBr (2.2 g, 20 mmol) were dissolved in HOAc (10 mL). The mixture was treated dropwise with 30% H2O2 (2.4 mL, 20 mmol) at room temperaturefor 1 h. Then, the mixture was quenched with water (8 mL) and extracted with diethyl ether (3 × 10 mL). The combined organic phases were washed with saturated NaHCO3 (3 × 5 mL) until pH 7, the combined the organic layers were dried over anhydrous Na2SO4, and evaporatedin vacuo to afford yellow oil 2 (5.2 g) in quantitative yield. 1H NMR (400 MHz, CDCl3): delta 6.61 (s, 1H, ArH), 3.89(s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.84 (s, 3H, OCH3),2.37 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3): delta 152.2, 150.8, 141.1,133.4, 110.8, 109.5, 61.1 (OCH3), 60.9 (OCH3), 56.1(OCH3), 23.2(CH3). Spectroscopic data are according to the literature (Wanget al. 2016).

The synthetic route of 1,2,3-Trimethoxy-5-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qiu, Yong-Fu; Lu, Bin; Yan, Yi-Yu; Luo, Wan-Yue; Wang, Jin; Hu, Xiao; Chemical Papers; vol. 73; 11; (2019); p. 2745 – 2748;,
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Synthetic Route of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

Under the protection of nitrogen, take 6mol / L hydrochloric acid 10.0ml, down to 0 ,9.0 ml of compound III ((dimethylamino) -acetaldehyde-diethyl acetal) was added dropwise, hydrolyzed at 40 ° C and cooled to 0 ° C for standby (A).To 100 ml of absolute ethanol, 10.00 g of the intermediate IV, 0.80 g of lithium chloride were added in this order, and the temperature was lowered to 04.0 g of sodium ethoxide was added, and the mixture was stirred for 30 minutes. The stock solution A was added dropwise, and the prepared liquid A was added dropwise.After the reaction was continued for 40 min, 250 ml of ethyl acetate was added, stirred for 1.0 hr, filtered, and 125 ml of water was added to the filtrate. In ThereThe organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure to give intermediate II. The yield in this step was about 84percent.

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

Reference:
Patent; Chongqing Weipeng Pharmaceutical Co., Ltd.; Lie, Zeyan; Zhou, Xingguo; Li, Chunlin; Han, Gongchao; (6 pag.)CN104529800; (2017); B;,
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Electric Literature of 82830-49-7, These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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 FIFTY-EIGHT: Synthesis of Ligand 24 (Figure 17); In a round-bottomed flask nBuLi (10 mmol, 4 rnL of a 2.5 M solution in hexanes) was added drop-wise to a solution of 1 ,4-dimethoxyfluorobenzene (10 mmol, 1.56 g) in THF (120 mL) at -78 0C. The mixture was stirred at -78 0C for a further 30 min, generating solution A. nBuLi (20 mmol, 8 mL of a 2.5 M solution in hexanes) was added drop-wise to a solution of 2,3-benzofuran (20 mmol, 2.36 g, 2.20 mL) in THF (30 mL) at 0 0C. After 2 h at this temperature the mixture was cooled to -78 0C and magnesium bromide (20 mmol, 3.68 g) added and this mixture stirred until the solid dissolved. This solution was then added via cannula to solution A and the mixture maintained at -78 0C for 1 h. The solution was then allowed to warm to room temperature overnight. The solution was then cooled to 0 0C and a solution of iodine (12 mmol, 3.5 g) in THF added via cannula. The mixture was allowed to warm to room temperature and sodium sulfite (saturated aq. solution) added. The mixture was extracted with EtOAc, the organic layer washed (water, then brine), dried and the solvent removed under reduced pressure. The residue was purified in 2 batches by column chromatography on a Biotage SP4 (hexane-EtOAc, 98:2 – 80:20) to give the iodide.

The synthetic route of 82830-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2009/76622; (2009); A2;,
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Application of 393-15-7, 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 393-15-7 as follows.

General procedure: 2-Bromoethyl amine (1 equiv.) and 4-Chlorphenylsulfonylchloride (1 equiv.) were dissolved in dry CH2Cl2under argon and triethyl amine (1.5 equiv) was added. The resultingreaction mixture was stirred at room temperature for 5 h. Then, waterand CH2Cl2 were added, followed by thorough extraction of theaqueous layer with CH2Cl2. The combined organic layer was driedover Na2SO4 and concentrated under reduced pressure. The residue waspurified via column chromatography (heptane/EtOAc, gradient 10:0 to1:1) to afford desired N-(2-bromoethyl)-4-chlorobenzene sulfonamideas intermediate which was dissolved in toluene (15 mL/mmol).Thereafter, a solution of KOH (3 equiv) in water (1 mL/mmol) wasadded. The resulting reaction mixture was stirred at room temperaturefor 90 min. After complete conversion, water and ethyl acetate wereadded, followed by thorough extraction of the aqueous layer withEtOAc. The combined organic layer was dried over Na2SO4 andconcentrated under reduced pressure. The residue was purified viacolumn chromatography (heptane/EtOAc, gradient) to afford desired 1-[(4-chlorophenyl)sulfonyl]aziridine as intermediate. 1-[(4-chlorophenyl)sulfonyl]aziridine (150 mg, 0.69 mmol), 4-fluoro-3-trifluoromethyl aniline (123 mg, 0.69 mmol) and SiO2 (100 mg,1.66 mmol) were then suspended in H2O (2 mL), and the resultingreaction mixture was treated with ultra sound for 90 min and wasstirred at room temperature for 20 h. Upon addition of water and ethylacetate the aqueous layer was extracted thoroughly with ethyl acetate.The combined organic layer was dried over Na2SO4 and concentratedunder reduced pressure. Purification of the remaining residue viacolumn chromatography (heptane/EtOAc, gradient) afforded N-(2-{[4-fluoro-3-(tri-fluormethyl)phenyl]amino}ethyl)-4-chlorobenzenesulfonamide

According to the analysis of related databases, 393-15-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Frackenpohl, Jens; Schneider, Linn; Decker, Luka J.B.; Dittgen, Jan; Fenkl, Franz; Fischer, Christian; Franke, Jana; Freigang, Joerg; Getachew, Rahel; Gonzalez Fernandez-Nino, Susana M.; Helmke, Hendrik; Hills, Martin J.; Hohmann, Sabine; Kleemann, Jochen; Kurowski, Karoline; Lange, Gudrun; Luemmen, Peter; Meyering, Nicole; Poree, Fabien; Schmutzler, Dirk; Wrede, Sebastian; Bioorganic and Medicinal Chemistry; vol. 27; 24; (2019);,
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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. Safety of 4-Methoxy-N-methylbenzylamine

A mixture of 3 -( 5 -amino-2-chloro-4-fluorophenyl )-7 -chloro-1-methyl-1, 6-naphthyridin-2(1H)-one (2.5 g, 7.4 mmol) and 4-methoxy-N-methylbenzylamine (4 mL) washeated to 180°C under N2 for 3 h. After cooling, the reaction mixture was diluted with Et20.The precipitate was filtered, washed with water, and dried to give 7-((4-methoxybenzyl )(me thy l)amino )-3 -( 5 -amino-2-chloro-4-fluorophenyl )-1-methyl-1, 6-naphthyridin-2(1H)-one (3 g, 89percent yield). 1H NMR (400 MHz, DMSO-d6): 8 8.47 (s, 1 H),7.77 (s, 1 H) 7.22 (m, 2 H), 7.17 (d, J = 8.0 Hz, 2 H), 6.86 (d, J = 8.4 Hz, 2 H), 5.86 (d, J =9.6 Hz, 1 H), 6.30 (s, 1 H), 5.32 (s, 2 H) 4.87 (s, 1 H), 3.72 (s, 3 H), 3.52 (s, 3 H), 3.09 (s, 3H); MS (ESI) m/z: 453.2[M+H(

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

Reference:
Patent; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2013/184119; (2013); A1;,
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Related Products of 366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of the amine (10.05mmol) in isopropanol (20ml) was added N,N-diisopropylethylamine (1.55g, 12mmol) and 2,4,5-trichloropyrimidine (1.84g, 10mmol). The reaction mixture was reflux for 2h followed by cooling to room temperature. Water (100ml) was added and the mixture was stirred for 30min. Then the mixture was filtrated. The solid was dried to provide the title compound 2a-2u.

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

Reference:
Article; Chen, Hong; Li, Ridong; Ning, Xianling; Zhao, Xuyang; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 141 – 153;,
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Reference of 20781-20-8, A common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

1-(2,4-Dimethoxyphenyl)methanamine (1.97 mL, 13.1 mmol) was added to a solution of 2-methyltetrahydro-4H-pyran-4-one (500 mg, 4.4 mmol) in methanol (10 mL). After stirring for 1 hour at room temperature, the reaction mixture was cooled to -78 C. and a solution of lithium borohydride (98%, 85 mg, 3.8 mmol) in tetrahydrofuran (1.5 mL) was added drop-wise. The reaction mixture was allowed to slowly warm to room temperature overnight, whereupon it was cooled to -20 C. and quenched via careful addition of saturated aqueous sodium bicarbonate solution. Ethyl acetate (25 mL) and sufficient water to solubilize the precipitate were added, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on silica gel [Gradient: 0% to 15% (10:1 methanol/concentrated ammonium hydroxide) in ethyl acetate] provided the product as a colorless oil. Yield: 936 mg, 3.53 mmol, 80%. 1H NMR (400 MHz, CDCl3) delta 7.13 (d, J=8.0 Hz, 1H), 6.46 (d, half of AB quartet, J=2.2 Hz, 1H), 6.44 (dd, half of ABX pattern, J=8.1, 2.3 Hz, 1H), 4.00 (ddd, J=11.6, 4.6, 1.6 Hz, 1H), 3.82 (s, 3H), 3.81 (s, 3H), 3.76 (s, 2H), 3.37-3.46 (m, 2H), 2.63-2.72 (m, 1H), 1.85-1.92 (m, 1H), 1.78-1.85 (m, 1H), 1.37 (dddd, J=13, 12, 11, 4.6 Hz, 1H), 1.20 (d, J=6.2 Hz, 3H), 1.10 (ddd, J=12, 11, 11 Hz, 1H)

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Galatsis, Paul; Henderson, Jaclyn Louise; Kormos, Bethany Lyn; Kurumbail, Ravi G.; Reese, Matthew Richard; Stepan, Antonia Friederike; Verhoest, Patrick Robert; Wager, Travis T.; Pettersson, Martin Youngjin; Garnsey, Michelle Renee; (150 pag.)US2017/73343; (2017); 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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., COA of Formula: C6F12O2

F[CF(CF3)CF2O]4CF(CF3)C(O)F, a precursor of hydrofluoroether F[CF(CF3)CF2O]5CH3, was formed by pentapolymerization of hexafluoropropylene oxide. To the reaction vessel, potassium fluoride (10.0 g), hexafluoropropylene oxide dimer (150.0 g) and diethylene glycol dimethyl ether (2.5 L) were added at 15 C under stirring.To the round bottom flask was introduced hexafluoropropylene oxide (830 g, 5.0 mol) over 1 hour.The lower layer of the acyl fluoride phase product is mainly composed of a hexafluoropropylene oxide tetramer, a hexafluoropropylene oxide pentamer and a hexafluoropropylene oxide hexamer, and the yield of the hexafluoropropylene oxide pentamer is 65%. The crude product was further purified by distillation to obtain a product of a hexafluoropropylene oxide pentamer having a purity of 99% as determined by gas chromatography, and used.In the next alkylation reaction. The structure of the product was characterized by infrared spectroscopy and 19F NMR.

The synthetic route of 2062-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Changlu Chemical New Materials Co., Ltd.; Yan Rui; He Guangrui; (15 pag.)CN109608312; (2019); A;,
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Synthetic Route of 109-85-3,Some common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, molecular formula is C3H9NO, 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.

(4-Bromo-6-chloro-quinolin-2-yl)-(4-fluoro-2-methoxy-benzyl)-amine (prepared from 2-amino-6-chloro-4-hydroxyquinoline and 4-fluoro-2-methoxybenzaldehyde as described in example 30, step A and B, 328 mg, 0.828 mmol) was dissolved in 5 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. 2-Methoxyethylamine (187 mg, 2.49 mmol), sodium tert.-butylate (159 mg, 1.66 mmol), 1,1′-bis(diphenylphosphino)ferrocene (69 mg, 0.125 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (34 mg, 0.042 mmol) were added. The reaction mixture was stirred in a sealed tube at 100 C. for 2 h. The solvent was evaporated and the residue purified by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0?110:10:1 gradient). 6-Chloro-N2-(4-fluoro-2-methoxy-benzyl)-N4-(2-methoxy-ethyl)-quinoline-2,4-diamine was obtained as an off-white foam (285 mg, 88%), MS: m/e=390.0 (M+H+).

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

Reference:
Patent; Kolczewski, Sabine; Riemer, Claus; Steward, Lucinda; Wichmann, Juergen; Woltering, Thomas; US2009/88451; (2009); A1;,
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