Author: Jessica.F

Reference of 22483-09-6,Some common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, molecular formula is C4H11NO2, 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: 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.

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-Dimethoxyethanamine, its application will become more common.

Reference:
Article; Shi, Zeyu; Xiao, Qiong; Yin, Dali; Chinese Chemical Letters; (2019);,
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Synthetic Route of 17715-69-4, 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 17715-69-4 as follows.

General procedure: A suspension of Pd2(dba)3 (6.9 mg, 0.0075 mmol), tBu3PHBF4 (8.7 mg,0.03 mmol), KOH (42 mg, 0.75 mmol), aryl bromide 9 (0.36 mmol) and tetralone 10(0.3 mmol) in a mixture of dioxane/water (4:1, v/v, 3 mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100 ¡ãC, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4,filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography.

According to the analysis of related databases, 17715-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Manvar, Dinesh; Fernandes, Talita De A.; Domingos, Jorge L.O.; Baljinnyam, Erdenechimeg; Basu, Amartya; Junior, Eurides F.T.; Costa, Paulo R.R.; Kaushik-Basu, Neerja; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 51 – 54;,
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Synthetic Route of 82830-49-7, A common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, molecular formula is C8H9FO2, 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: To an oven-dried round-bottom flask with a stir bar were charged with a solution of secondary amines 2 (1.5 mmol) in 1 mLdry THF at room temperature under an argon atmosphere. To thissolution was slowly added 1.2 mL nBuLi (2.5 mol/L in n-hexane,3.0 mmol) via syringe. After stirring at 25 C for 10 min, a solution of fluoroarene 1 (1.0 mmol) in 1mL dry THF was added to the reaction flask. The reaction mixture was stirred for 0.5 h at 25 C, and then quenched with 2 mL saturated aqueous solution of NaCl and extracted with H2O (20 mL) and ethyl acetate (3 20 mL). The organic layer was separated and dried with anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude product was purified by column chromatography on silica gel using a petroleum ether/ethyl acetate mixture as eluent to afford the pure target compounds.

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:
Article; Lin, Yingyin; Li, Meng; Ji, Xinfei; Wu, Jingjing; Cao, Song; Tetrahedron; vol. 73; 11; (2017); p. 1466 – 1472;,
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Adding a certain compound to certain chemical reactions, such as: 109-85-3, name is 2-Methoxyethylamine, 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 109-85-3, Application In Synthesis of 2-Methoxyethylamine

To a stirred solution of tert-butyl 4-oxopiperidine-l -carboxylate (2 g, 10.04 acetic acid (0.575 mL, 10.04 mmol) and 2-methoxyethanamine (0.754 g, 10.04 mmol) in MeOH (40 mL) under N2 was cooled to 0 C. Then the mixture was added NaCNBH4 (0.631 g, 10.04 mmol) and stirred at RT for 16 hrs. The reaction mixture was quenched with 50 mL of aqueous 10% NaHC03 solution and extracted with EtOAc (2 x 200 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography gave 103 A (liquid, 1.5 g, 5.81 mmol, 58 % yield). GC-MS Anal.Calc?d for C]3H26N203 258.2, found 157.2 (M- Boc). Tr = 9.43 min (Method AE).

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-Methoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); A1;,
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Reference of 150-78-7, The chemical industry reduces the impact on the environment during synthesis 150-78-7, name is 1,4-Dimethoxybenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 61 (+,-)-N-(cis-2-(3,6-dimethoxy-2-fluorophenyl)-cyclopropyl)-N’-(5-chloropyrid-2-yl)-urea To a solution of 1,4-dimethoxybenzene (15.0 g, 0.109 mol) in 300 mL of dry THF was added 2.5M n-butyllithium (45.6 mL, 0.114 mol) at room temperature under nitrogen. After addition was complete, the solution was stirred for 1 hr. The mixture was cooled to -70 C. and N-fluorobenzenesulfonimide (36.0 g, 0.114 mol) in 150 mL of THF was added slowly, keeping the temperature below -60 C. The solution was allowed to warm to room temperature during the night. 100 mL of NH4 Cl (sat) was added and the mixture was extracted with diethyl ether/THF. The organic phase was washed with 1M NaOH (2*60 mL), dried over MgSO4 and evaporated. Column chromatography (silica gel, n-hexane followed by 1, 5 and 10% EtOAc in n-hexane) provided 11.43 g of a mixture of 1,4-dimethoxy-2-fluorobenzene and 1,4-dimethoxybenzene (4.3:1). This mixture was reacted in a manner analogous to Examples 362, 375 and 348 of WO 93/03022 to give (+,-)-cis-2-(3,6-dimethoxy2-fluorophenyl) cyclopropylamine.

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, 1,4-Dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Medivir AB; US5849769; (1998); A;,
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These common heterocyclic compound, 5397-31-9, name is 3-((2-Ethylhexyl)oxy)propan-1-amine, 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. COA of Formula: C11H25NO

c) 19.9 parts of the trisazo dyestuffs of part b) above are suspended in 100 parts of water, 10.0 parts of [DIPROPYLENE] glycol monomethyl ether and 4. [8] parts of sodium acetate. After warming at [96C] for over one hour, 5.9 parts of copper sulphate are added in small portions for over one hour, followed by 20.0 parts of 25% ammonia. The mixture is heated to reflux for 12 hours whereupon a voluminous suspension of the copper complex results. The temperature is allowed to fall to [45C] over 2 hours (while stirring well) and the suspension is slowly reacted with a solution of 13.3 parts of [3-[(2-ETHYLHEXYL) OXY]-1-] propanamine in 70 parts of water and [8.] 3 parts of 30% HCI. The resulting precipitate is stirred a further hour at room temperature, filtered and the residue is washed salt free and dried. A compound of formula wherein R is methoxy, is obtained.

The synthetic route of 3-((2-Ethylhexyl)oxy)propan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CLARIANT INTERNATIONAL LTD; WO2003/99937; (2003); 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1836-62-0

Example 1 Preparation of Carvedilol in Neat Conditions 2-(2-Methoxyphenoxy)ethylamine (III) (4.89 g) was heated to about 100 C., after which 4-(oxiran-2-ylmethoxy)-9H-carbazole (II) (3.31 g) was added portionwise. After approximately 20 minutes, the reaction mixture was cooled to about 70 C., after which water (25 ml) and ethyl acetate (15 ml) were added. The pH of the two-phase mixture was then adjusted to 5 with 2 N hydrochloric acid. The solid that formed, Carvedilol hydrochloride hydrate, is filtered, washed with water (20 ml) followed with ethylacetate (15 ml). The resulting material is reslurried in ethylacetate (50 ml) and water (20 ml) containing 5% Sodium carbonate until the pH reached 7.5. The organic phase was separated and dried over sodium sulfate. The dried solution was concentrated to a turbid solution and cooled overnight to about 4 C. Precipitated carvedilol was isolated by filteration and crystallized from isopropanol.

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 1836-62-0.

Reference:
Patent; Hildesheim, Jean; Finogueev, Sergey; Aronhime, Judith; Dolitzky, Ben-Zion; Ben-Valid, Shoshana; Kor, Ilan; US2002/143045; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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 20781-20-8, Safety of (2,4-Dimethoxyphenyl)methanamine

a. Potassium carbonate (2.97 g, 21.5 mmol) was added to a mixture of 2- chloropyrimidine (2.1 g, 17.9 mmol), 2,4-dimethoxybenzylamine (3.0 g, 17.9 mmol) and acetonitrile (20 mL). The reaction mixture was heated at reflux for 16 h, allowed to cool to ambient temperature and partitioned between ethyl acetate (150 mL) and water (10 mL). The organic phase was washed with water (2 10 mL) and brine (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was triturated in diethyl ether (20 mL), washed with hexanes (20 mL) and purified by column chromatography, eluting with a 0-100% gradient of ethyl acetate in hexanes to afford A/-(2,4-dimethoxybenzyl)pyrimidin-2-amine as a pale yellow solid in 84% yield (3.70 g): MS (ES+) m/z 245.9 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2,4-Dimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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 29578-83-4, COA of Formula: C8H9BrO

A mixture of NBS (5.31 g, 29.83 mmol, 1.20 equiv), AIBN (2.04 g, 12.42 mmol, 0.50 equiv), Cd4 (100 mL), and 1-bromo-3-methoxy-5-methylbenzene (5.00 g, 24.87 mmol, 1.00 equiv) was stirred for 12 h at 80C under nitrogen. The reaction was then quenched by water, extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:100) to afford the title compound (6 g, 86%) as a light yellow solid.

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, 1-Bromo-3-methoxy-5-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
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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 31804-36-1 as follows. category: ethers-buliding-blocks

(E)-ethyl 3-(3-methoxy-2-methylphenyl)acrylateTo a solution of 1-bromo-3-methoxy-2-methylbenzene (515 mg, 2.56 mmol) in DMF (10 ml_) at RT was added ethyl acrylate (2564 mg, 25.6 mmol) and N-ethyl-N- isopropylpropan-2-amine (2.68 ml_, 15.37 mmol), tri-o-tolylphosphine (312 mg, 1.025 mmol), Pd(OAc)2(1 15 mg, 0.512 mmol). The reaction mixture was heated in microwave under high absorption at 150 C for 2 h. The reaction mixture was passed through celite and washed with EtOAc. The filtrate was washed with water twice, brine (1x). The organic layer was collected and concentrated to give the crude product. The crude product was purified on a silica cartridge (40 g) with a Combiflash Companion, eluting at 35 mL/min with a gradient running from 0 % EtOAc/hexanes to 50 % over 35 min. The desired fractions were concentrated under reduced pressure to give 450 mg (80 %) of the title compound. LC-MS m/z 220.9 (M+H)+, 1.11 (ret. time).

According to the analysis of related databases, 31804-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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