Ethers-buliding-blocks

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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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Ether | (C2H5)2O – PubChem

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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Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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 mixture of 3′,4′-dichloro-4-fluorobiphenyl-3-carbonitrile (173 mg, 0.650 mmol), 4-isopropoxyaniline (108 mg, 0.715 mmol), and KOtBu (154 mg, 1.375 mmol) in DMSO (4mL) was stirred at rt for 1.5h, The mixture was diluted with ethyl acetate, washed with H2O and brine, and then dried over Na2SO4. The solvent was removed and the product was purified by silica gel chromatography (eluting with hexane containing 0 to 8% ethyl acetate) followed by preparative HPLC (100 x 30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B =50:50 and ending with A:B =0: 100 [A = 10 mM NH4OAc in 5% aqueous acetonitrile; B = IO mM NH4OAc in 95% aqueous acetonitrile] over 20 min). This afforded 99 mg of 3′,4′-dichloro-4-(4-isopropoxyphenylamino)-biphenyl-3- carbonitrile which still contained some impurities according to the LC/MS but was used as such for next step. MS (ESI) m/z 397.1 (M+H).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok, Vinayak; BATT, Douglas, G.; LIU, Qingjie; JOHNSON, Walter, L.; MASTALERZ, Harold; ZHANG, Guifen; ZIMMERMANN, Kurt; WO2010/80474; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 1535-73-5, name is 3-Trifluoromethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Trifluoromethoxyaniline

Example 6 : (+/-) 3-{f(3-trifluoromethoxyphenyl)amino1carbonyl)-1 ,2,2- trimethylcvclopentanecarboxylic acidA mixture of (+/-) camphoric acid anhydride (0.92 g, 5.05 mmol), anhydrous sodium acetate (0.5Og, 6.09 mmol) and 3-(trifluoromethoxy)aniline (1.015 g, 5.73 mmol) were heated in an oil bath at 140cC for 2 hours. The mixture was removed from the oil bath to cool sufficiently to add water (4 ml) and ethyl acetate (4ml). The mixture was stirred with heating to dissolve the solids before diluting with more ethyl acetate (20ml) and dilute hydrochloric acid (20 ml, 1M). The organic layer was taken and partially evaporated under vacuum to give a viscous oil. The oil was dissolved in ethyl acetate (6 ml) and then petroleum ether (6 ml, 40-60) added. The crystals that formed were collected and washed with more ethyl acetate/petroleum ether (1 :3, 6 ml) and dried under vacuum to give (+/-) 3-{[3-trifluoromethoxyphenyl)amino]carbonyl}- 1 ,2,2-trimethylcyclopentanecarboxylic acid as a white powder (0.97 g, 53percent yield) ; 1 H-NMR (400 MHz1 d6-DMSO) : 612.22 p.p.m. (s, 1 H), 10.01 (s, 1 H), 7.84 (S1 1 H)1 7.56 (m, 1 H)1 7.46 (t, J = 8 Hz, 1 H), 7.04 (m, 1 H), 2.91 (t, J = 9.4 Hz, 1 H), 2.49 (m, 1 H), 2.08 (m, 1 H)1 1.79 (m, 1 H), 1.46 (m, 1 H), 1.22 (s, 6H), 0.82 (S, 3H).

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 1535-73-5.

Reference:
Patent; MERLION PHARMACEUTICALS SA; MERLION PHARMACEUTICALS PTE LTD; WO2008/17840; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 2062-98-8 as follows. category: ethers-buliding-blocks

To a solution of hydroxyacetone (7.4 g) and pyridine (8.1 ml) in ethyl acetate (100 ml), undecafluoro-(2-methyl-3-oxahexanoic acid)fluoride (10 g) was added dropwise at room temperature (25 C.). After stirring at room temperature for 2 hours, the reaction mixture was poured into diluted hydrochloric acid. After separation, the organic layer was washed with water and a saturated sodium chloride solution and dried with magnesium sulfate. The concentrated residue was purified by column chromatography (developing solvent: ethyl acetate/hexane), to obtain Compound B (10.2 g, 88%).1H NMR (CDCl3) delta 2.22 (s, 3H), 4.85 (d, J=16.2 Hz, 1H), 4.96 (d, J=16.2 Hz, 1H)19FNMR (CDCl3) delta -80.3 (1F), -81.8 (3F), -82.5 (3F), -86.7 (1F), -130.2 (2F), -132.8 (1F)

According to the analysis of related databases, 2062-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; US2009/18350; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

Roundbottom flask is charged with 5-bromo-2-methylaniline( 400.00 mg; 2.15 mmol; 1 .0 eg.), triethylamine ( 330.76 mL; 2.36 mmol; 1.1 eq.) and anhydrous dichloromethane (12 mL). Acetyl chloride ( 185.64 mg; 2.36 mmol; 1.1 eq.) is then added dropwise and reaction mixture is stirred at room temperature for 24h. After this time diethyl ether (24 mL) is added and mixture is washed with saturated aqueous solution of ammonium chloride (2×20 mL) and brine (2×20 mL). Organic layer is then dried over anhydrous Na2SO4 overnight. The second organic solvent is evaporated to afford N-(5- bromo-2-methylphenyl)acetamide (513.20 mg; yield 93.5 %; 89.3 % by UPLC) as brown solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem