Month: August 2021

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. 33170-72-8, name is 2-Bromo-1,1-dimethoxypropane, A new synthetic method of this compound is introduced below., Recommanded Product: 33170-72-8

[0157] To a stirred solution of 3,5-bis(methylthio)-l ,2,4-triazin-6-amine (10.0 g, 53.19 mmol) and 2-bromo- 1 , 1 -dimethoxypropane (19.6 g, 319.14 mmol, 2 times added), in CH3CN (120 mL) was added (+/-)-camphor-10-sulfonic acid (3.70 gm, 15.95 mmol) and MS-4A (2 g). and the mixture was heated at 85 C for 40 h. The mixture was cooled to RT and concentrated under reduced pressure to reduce the volume to 30 mL. The obtained solid was filtered and washed with CH3CN (10 mL). The solid was dissolved in 20% MeOH in CH2CI2 and filtered, and the filtrate was concentrated under reduced pressure to afford 7- methyl-2,4-bis(methylthio)imidazo[l ,2-f][1,2,4]triazine as a pale brown solid (7 g, 58%). 1H NMR (300MHz, DMSO-J6) delta 7.59 (br s, IH), 2.63 (s, 3H), 2.60 (s, 3H), 2.48 (s, 3H); MS (ESI) m/z 227.12 [M+H]+.

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; KALYRA PHARMACEUTICALS, INC.; BUNKER, Kevin, Duane; ABRAHAM, Sunny; HOPKINS, Chad, Daniel; PINCHMAN, Joseph, Robert; HUANG, Peter, Qinhua; SLEE, Deborah, Helen; (122 pag.)WO2016/183094; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8, Quality Control of 4-(Difluoromethoxy)aniline

General procedure: Step-1:4-amino-2,6-dichloro pyrimidine: 2,4,6-trichloro pyrimidine (1.0 mmol) in ethanol (5 mL) was treated with an aromatic amine (1.1 mmol) in the presence of Na2CO3 (1.1 mmol) at rt. The mixture was stirred at reflux for 2-4 h until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, an equal volume of water was added with cooling. The resulting white precipitate was filtered, washed with water, and dried in vacuum over night to yield 4-substituted 2,6-dichloro pyrimidine. In case of no precipitation, ethanol was removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 4-amino-2,6-dichloro pyrimidines in 85-95% yield. Step-2: 2,4-diamino-6-chloropyrimidine: 4-amino-2,6-dichloro pyrimidine (1.0 mmol) prepared from the above procedure was treated with another aliphatic amine or aromatic amine (2.0 mmol) in the presence of DIEPA (5.0 mmol) in n-BuOH (5 mL) at rt. For an aliphatic amine the reaction mixture was stirred at rt for overnight. For an aromatic amine the reaction mixture was refluxed for 24-72 h or placed in microwave (150 C, 2-7 h) until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, solvents were removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography (EtOAc/hexane) to afford the 2,4-diammino-6-chloropyrimidines in 85-90% yield. Step-3: 2,4,6-triaminopyrimidine: 2,4-diamino-6-chloropyrimidine (1.0 mmol) prepared from the above procedure was treated with another suitable aliphatic amine or aromatic amine (3.0 mmol). For an aliphatic amine, 2,4-diamino-6-chloropyrimidine (1.0 mmol) was treated with aliphatic amine (3.0 mmol) and DIPEA (5.0 mmol) in n-BuOH (5 mL) and placed in microwave (150 C) for 3-7 h. After the completion of the reaction (monitored by TLC), solvents were removed and the residue was dissolved in EtOAc. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 2,4,6-triaminopyrimidines 90-95% yield. For aromatic amine; 2,4-diamino-6-chloropyrimidine (1.0 equiv) was dissolved in dioxane under argon and to that were added Pd2(dba)3 (10 mol %), Xantphos (10 mol %), aromatic amine (1.2 mmol), t-BuOK (1.2 mmol). The resulting solution was degassed with argon for 5 min and heated to 85 C for overnight. The reaction mixture was filtered through a pad of celite, washed with CH2Cl2 (2 × 10 mL) and the resulting filtrate was concentrated. The resulting crude was purified by flash column chromatography to yield 2,4,6-triaminopyrimidines in 90-95% yield.

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, 4-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sagi, Vasudeva Naidu; Liu, Tianyu; Lu, Xiaoying; Bartfai, Tamas; Roberts, Edward; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7210 – 7215;,
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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. Product Details of 592-55-2

2-(2-ethoxyethoxy)-1 ,3-dimethylidene-2,3-dihydro-1 H-isoindole (1-18) The N-hydroxypthalimide (4.0 g) and 1 -bromo-2-ethoxyethane (11 .25 g) were dissolved in DMF (40.0 ml) and CH3000Na (10.0 g) was added to the solution at room temperature. The reaction mixture was allowed to stir at 70 00 for 12 hours. Thereaction mixture was allowed to cool to room temperature and was and was poured in water and then extracted two times by ethyl acetate. The organic layer was concentrated under reduce pressure and was purified by column chromatography using silica gel. The desired product was eluted with 0-30% ethyl acetate in hexane. Evaporation of pure product fractions gave 4.8 g of 2-(2-ethoxyethoxy)-1 ,3-dimethylidene-2,3-dihydro-1H-isoindole (1-18) (Yield: 83.3 %). 1H-NMR (DMSO-d6): (ppm) 0.98 (t, 3H),3.39 (q, 2H), 3.73 (t, 2H), 4.27 (t, 2H), 7.87 (s, 4H). LC-MS: mlz= 236.2 (M+H).

The synthetic route of 1-Bromo-2-ethoxyethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INFLECTIS BIOSCIENCE; GUEDAT, Philippe; (110 pag.)WO2016/1390; (2016); 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of ((2-Bromoethoxy)methyl)benzene

In a round bottom flask aniline (2.0 g, 21.5 mmol, 2.0 mL), 2,6-lutidine (2.30 g, 21.5 mmol) and benzyl 2-bromoethyl ether (4.6 g, 21.5 mmol, 3.4 mL) were combined in DMF (10 mL) and stirred at 100° C. overnight. The reaction was allowed to cool and then diluted with ethyl acetate (50 mL). This was washed with water (3*20 mL) and the organics were dried and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (0-50percent B, 100 g, 19.5 CV, 85 mL/min) to afford 2.22 g (37percent) of (2-benzyloxy-ethyl)-phenyl-amine (21) as a yellow oil. The structure was confirmed by 13C NMR (75 MHz, CDCl3) deltaC 43.6, 68.6, 73.2, 113.1, 117.5, 127.5, 127.7, 128.4, 129.1, 138.2, 148.1.

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; GE Healthcare Limited; Jones, Paul Alexander; US9168317; (2015); B2;,
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Adding a certain compound to certain chemical reactions, such as: 4393-09-3, name is (2,3-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 4393-09-3, Safety of (2,3-Dimethoxyphenyl)methanamine

In a 20 mL scintillation vial, 4-amino-5-cyano-6-ethoxy-pyrindine-2-carboxylic acid (19 mg, 0.09 mmol) was dissolved in DMA (0.7 mL). Then TBTU (30 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added, followed by the addition of 2,3-dimethoxylbenzylamine (17 mg, 0.11 mmol, 1.2 eq.) in DMA (0.6 mL). Then TEA (9.37 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added. The mixture was shaken at room temperature for 24 hours. The crude mixture was purified using reverse phase HPLC (TFA). 1H NMR (500 MHz, DMSO-D6/D2O) delta ppm 1.28 (t, 3H) 3.80 (d, 6H) 4.26-4.66 (m, 4H) 6.67-7.19 (m, 4H) 8.87 (t, 1H). MS (ESI) positive ion 357 (M+H)+; negative ion 355(M-H)-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2,3-Dimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; Liu, Gang; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Liu, Mei; US2006/173050; (2006); 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. 170015-99-3, name is 2-(4-(Trifluoromethoxy)phenyl)ethanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H10F3NO

Preparation of Intermediate Ethyl 4-(trifluoromethoxy)phenethylcarbamate (I-51c) Using an analogous procedure and workup as described for the preparation of intermediate I-1c above, 2-(4-(trifluoromethoxy)phenyl)ethanamine (I-51b: 3.1 g, 15.1219 mmol) in chloroform (31 mL) was reacted with chloro ethyl formate (1.72 mL, 18.146 mmol) and 2N Na2CO3 solution (31 mL) at 0 C. The resulting mixture was stirred at room temperature for 3 hours to afford the crude product. Purification by column chromatography on silica gel (10% ethylacetate in hexane) afforded 3.2 g of the product (76% yield). 1H NMR (300 MHz, CDCl3): delta 7.30-7.10 (m, 4H), 4.75-4.65 (m, 1H), 4.15-4.05 (m, 2H), 3.4 (q, 2H), 2.8 (t, 2H), 1.3-1.2 (m, 3H). LCMS: 70.91%, m/z=278.1 (M+1)

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 170015-99-3.

Reference:
Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); A1;,
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These common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, 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. Quality Control of 4-(Trifluoromethoxy)benzene-1,2-diamine

To a solution of 1, 2-diamino-4-trifluoromethoxybenzene (35g, 180 mmol) in tetrahydrofuran (350 ml) was added urea (32 g, 180 mmol). The solution was refluxed at 7O0C overnight, concentrated under vacuum to a volume of about 100 mL and diluted with water (500 mL). The suspension was stirred at room temperature overnight and filtered. The solid was washed with water and dried under vacuum to obtain a white crystalline solid. LC-MS: m/e (M+l) = 219. 1H NMR (DMSO, 500 MHz) delta 10.85 (d, J=8Hz, 2H), 6.97 (d, J=8.5Hz, IH), 6.90 (d, J=I lHz, 2H).

The synthetic route of 4-(Trifluoromethoxy)benzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/22954; (2006); A2;,
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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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H14ClNO

4-BenzyloxyanilineHCl (86.1 mmol, 20.3 g), diethylbromomalonate (86. 1mmol, 14.7 ml) and N, N-diisopropylethylamine (86.1 mmol, 15 ml) in toluene (200 ml) was heated at 100C for 36 hours. The reaction mixture was concentrated, dissolved in water (500 ml) and extracted with EtOAc (3 X 300 ml). The organic phase was dried over Na2S04, concentrated and purified by flash chromatography (Si02, 50% EtOAc/hexanes) to provide compound 4A as a brown solid (13.7 g, 45%)

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; BRISTOL-MYERS SQUIBB COMPANY; WO2003/91252; (2003); A1;,
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Reference of 450-91-9, The chemical industry reduces the impact on the environment during synthesis 450-91-9, name is 4-Fluoro-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

Ice bath,4-Fluoro-2-methoxyaniline (6.5 g, 46 mmol) was dissolved in concentrated sulfuric acid (50 mL)After stirring for 30 minutes in an ice bath,Potassium nitrate (5.2 g, 51 mmol) was added portionwise,After the addition, the reaction was allowed to proceed to room temperature and the reaction was stirred for 12 hours.After completion of the reaction,The reaction was poured into ice and the pH was adjusted to 8 with the addition of ammonia, Ethyl acetate (200 mL × 3), dried over anhydrous sodium sulfate,Concentrated, and purified by column chromatography (petroleum ether: ethyl acetate = 3: 1) to give the title compound (6.9 g, yield 80%).

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, 4-Fluoro-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd; Wu, Yongqian; (68 pag.)CN105884695; (2016); A;,
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These common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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: C5H10Br2O2

Reference Example 2; Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylateTo DMF solution (1.8 L) comprising diisopropyl malonate (1437 g), sodium hydride (367 g) was added at 15 C. Subsequently, 1,3-dibromoacetone dimethylacetal obtained from Reference example 1 was added thereto, stirred at 130 C. for 24 hours, followed by further stirring for three days. Upon the completion of stirring, the reaction was terminated by adding aqueous solution of ammonium chloride, and extraction was carried out using hexane. The organic layer was washed with water, and then dried over magnesium sulfate. Solids were removed, and the filtrate was dried under reduced pressure. Thus obtained residues were subjected to flash column chromatography (using 10:1 (v/v) hexane/ethyl acetate as an eluent) to obtain the title compound (1.5 kg).1H-NMR (CDCl3): 5.08 (2H, m), 3.15 (6H, s), 2.69 (4H, s), 1.24 (12H, m).

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

Reference:
Patent; Asahi Kasei Pharma Corporation; US2009/298894; (2009); A1;,
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