Ethers-buliding-blocks

1462-37-9, These common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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.

Step b: Ethyl 1 -(2-(benzyloxy)ethyl)-4-(terf-butyldimethylsilyloxy)cyclohexanecarboxylate; [00165] To a mixture of the compound of Step a (102 g, 0.357mol) in THF (800 mL) at -78 0C was added lithium bis(tritnethylsiyl)amide (438 mL) dropwise under nitrogen. The mixture was stirred for 30 min followed by the addition of benzyl 2-bromoethyl ether (109 mL, 0.375mol). After stirring the mixture for another 30min at -78 ¡ãC, the reaction mixture was allowed to warm up to room temperature and stirred for 1 h. The mixture was diluted with ethyl acetate (1,000 mL) and washed with brine (1,000 mL), dried over Na2SO4 and filtered. The filtrate was concentrated to give a crude product which was purified by flash chromatography (silica gel, EtOAc/Hexane: 0/1 to 1/1) to give the ester-benzylether as a colorless oil (1 15 g, 73percent).

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 1462-37-9.

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
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1484-26-0, Adding some certain compound to certain chemical reactions, such as: 1484-26-0, name is 3-Benzyloxyaniline, 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 1484-26-0.

2-Ohtoeroethyl isothiocyanate (293 ing, 2.4 mroot) was added io a solution of 3~bepsilonnzy)oxy~pheny)amine (398 mg, 2,0 mmoi) in dicMoromethane (4 mL), The reaction mixture was stirred at room temperature overnight It was quenched with water (30 mL), followed by extraction with diehloromethane OO mL x 3 ), The organic layers were combined, washed with brine, and concentrated under vacuum. The residue thus obtained was subjected to column chromatography on silica gel to give l -(3-benlambda’ioxy-plienyl)-3-{2-chloro-ethyl)-{hioufea (627 mg, 1.96 mmoi. yield; 98percent) as colorless oil.Tricihylarmne (2.0 mL, excess) was added to a solution of i ~(3-be”zyloxy- phctty.)-3-(2-chloro-ethyl)-mionrea ( S 87 mg, 0.58 mmol} in dry THF (3 mL). The reaction mixture was stirred at refluxiog temperature for 6 hours. It was then quenched with a saturated ammonium chloride aqueous solution {30 niL), followed by extraction with ethyl acetate (30 mL x 3), The organic layers were combined, washed with brine, and concentrated under vacuum. The residue thus obtained was subjected Jo column chromatography on silica gei to give l-(3-benz.yloxy~phenyl>- imidazoiidine-2-thione (compound 76) as a white solid (150 mg. 0.52 mmoi, yield: 90percent).Fi-MS (M-M ): 285.

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 1484-26-0.

Reference:
Patent; NATIONAL HEALTH RESEARCH INSTITUTES; WO2008/22204; (2008); A2;,
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20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below.

To a solution of 5-fluoro-2-nitrobenzoic acid (6.6 g,35.66 mmol) in dichloromethane (100 mL) were added DIPEA (9.22 g, 71.3 mmol), HOSt (6.0 g, 39.2 mmol) and EDCI (10.2 g, 53.5 mmol). After about 15 mm stirring, to the reaction mixture was added a solution of 2,4-dimethoxy- benzyl amine (5.96 g, 35.66 mmol) in dichloromethane (50 mL) dropwise under nitrogen atmosphere. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 16 h. The reaction mixture was washed successively with iN HC1 (100 mL), sat. NaHCO3 (100 mL) and brine (100 mL). The organic phase was then dried over MgSO4. Filtration and solvent removal in vacuo afforded a yellowish solid, wt: 9.3 g (78%). MS: [M+1]=335.

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; AgeneBio, Inc.; Mekonnen, Belew; Butera, John A.; Huang, Jianxing; (331 pag.)US2018/170941; (2018); A1;,
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1535-73-5, name is 3-Trifluoromethoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 1535-73-5

As shown in Scheme 4, Compound 3 was prepared in the following manner. To a solution of 2-methyl-1-(3-morpholinopropyl)-5-phenyl-1H-pyrrole-3-carboxylic acid 7 (100 mg; 0.305 mmol) in 5 mL DCM was added thionyl chloride (111 muL; 1.53 mmol) and DMF (20 muL). After stirring for 3 h at rt, the reaction mixture was evaporated and dried under vacuum. To the residue was added DCM (3 mL), 3-trifluoromethoxyaniline 11 (108 mg; 0.61 mmol), and DIPEA (0.22 mL; 1.2 mmol), and the reaction mixture was stirred overnight. To the reaction mixture was added water, and the mixture was extracted with DCM. The organic phase was washed with water, brine, dried by anhydrous sodium sulfate, concentrated, and purified by chromatography to provide Compound 3 (99 mg; 0.203 mmol, 67percent yield). 1H-NMR (CD3OD/400 MHz): delta 7.80 (s, 1H); 7.58 (d, 1H); 7.40 (m, 6H); 6.96 (d, 1H); 6.65 (s, 1H); 4.08 (m, 2H); 3.57 (m, 4H); 2.64 (s, 3H); 2.30 (m, 6H); 1.67 (m, 2H). 19F-NMR (CD3OD/376 MHz): ?59.73 (s). MS (ES+, m/z): 488.0 (M++1, 100.0).

Statistics shows that 1535-73-5 is playing an increasingly important role. we look forward to future research findings about 3-Trifluoromethoxyaniline.

Reference:
Patent; Krizaj, David; Prestwich, Glenn D.; Barabas, Peter; Xu, Yong; Ryskamp, Daniel; US2013/303539; (2013); 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 437-82-1 as follows. 437-82-1

26 g (180 mmol) of 2,6-difluoroanisole and 14.6 ml (198 mmol) of cyclopropyl cyanide in 500 ml of toluene are admixed dropwise at 0 C. over 40 min with 396 ml of a 0.5 molar (198 mmol) solution of bis(trimethylsilyl)potassium amide in toluene. The mixture is stirred at room temperature for 18 hours and admixed with water and 1M sulphuric acid, with ice cooling. The organic phase is separated off and the aqueous phase is extracted repeatedly with ethyl acetate. The extracts are washed with brine, dried with sodium sulphate and concentrated in vacuo. Purification by chromatography on silica gel (hexane/ethyl acetate 10%-20%) gives 12.7 g of 1-(3-fluoro-2-methoxyphenyl)cyclopropylnitrile.

According to the analysis of related databases, 437-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Schacke, Heike; Baurle, Stefan; Schmees, Norbert; US2007/225290; (2007); A1;,
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A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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. 6346-09-4.

Synthesis of phthalimide lb.; To a stirred solution of 4-aminobutyraldehyde diethyl acetal la (89.3 mmol) in CH3CN (100 mL) was added N-carbethoxyphthalimide (93.8 mmol). Once the reaction was complete, the acetonitrile was removed under reduced pressure and the aqueous phase extracted with EtOAc (x3). The organic phase were combined, then washed with water (x4), saturated brine (x3), then dried (Na2S04), filtered, and evaporated under reduced pressure to give the title compound lb, which crystallized on standing.

The synthetic route of 4,4-Diethoxybutan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; WO2005/70930; (2005); A2;,
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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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., 111-95-5

(1)N’5′-[2-Chloro-4-(trifluoromethyl)phenyl]-N’5′-ethyl-2-(4-methoxybenzyl)-N’7′,N’7-bis(2-methoxyethyl)-2H-pyrazolo[4,3-d]pyrimidine-5,7-amine A mixture of 7-chloro-N-[2-chloro-4-(trifluoromethyl)phenyl]-N-ethyl-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine-5-amine(a compound obtained in Reference Example 16) (75 mg), N,N-diisopropylethylamine(18.2 mg) and bis(2-methoxyethyl)amine(93.7 mg) in N-methylpyrrolidone(1.1 mL) was stirred at outside temperature of 110C under argon gas atmosphere overnight. After being cooled to room temperature, water and chloroform were added to the reaction mixture, the separated organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was evaporated under reduced pressure. The resulted residue was purified by using a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:2) to give the titled compound(84.3 mg) quantitatively as a pale yellow liquid. MS(APCI)m/z:593/595[M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1903045; (2008); A1;,
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52189-63-6, Adding some certain compound to certain chemical reactions, such as: 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, 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 52189-63-6.

Boron tribromide (1 M in dichloromethane, 9mL, 89.985mmol) was added drop wise to an ice- cooled solution of 3,5-dimethoxy fluorobenzene (3ml, 22,496mmol) in dichloromethane (2OmL) and the mixture was stirred at O0C to room temperature for 4 hours. The solution was cooled to O0C, further boron tribromide (4ml, 44.992mmol) was added and stirring continued, warming to room temperature for an additional 18 hours. The reaction was quenched with 0.88 ammonia solution and stirred at room temperature for 90 minutes. The organic layer was separated and extracted with 2N sodium hydroxide (30ml), which was then acidified to pH1 by drop wise addition of concentrated hydrochloric acid. The aqueous layer was then re- extracted with dichloromethane (3x15mL), the combined organic solution was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid in 54% yield, 1.72g. 1HNMR(400MHz, CD3OD) delta: 3.72(s, 3H), 6.07-6.15(m, 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 52189-63-6.

Reference:
Patent; PFIZER LIMITED; WO2007/34325; (2007); A1;,
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929-75-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 929-75-9 name is 1,11-Diamino-3,6,9-trioxaundecane, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

N-i^e-Dichlorotl^^Jtriazin^-y -HO-dimethyl-hydroxylamine (XXX) (1.63 g, 7.8 mmol) in EtOH (100 mL) was added to 2,2′-(2,2*-oxybis(ethane- 2,l-diyl)bis(oxy))diethanamine {Org. Biomol. Che . 2005, 3:2255-61) (1.5 g, 7.8 mmol) and DIPEA (2.01 g, 15.6 mmol). The reaction was heated at 100 C for 3 h, after which time the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (200 mL), washed with water (2 x 100 mL) and then with a brine solution (100 mL) and lastly dried over Na2S0 . The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (DCM MeOH=50/l to 20/1) to yield N-(5,8,l l-trioxa-2, 14,16,18,19- pentaazabicyclo[l 3.3.1 ]nonadeca-l(l 8), 15( 1 ), 16( 17)-trien-l 7-yl)-N,0- dimethylhydroxylamine (CXVII) (700 mg) as a colourless oil (yield 27%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,11-Diamino-3,6,9-trioxaundecane, and friends who are interested can also refer to it.

Reference:
Patent; GALLEON PHARMACEUTICALS, INC.; DAX, Scott, L.; WOODWARD, Richard; PENG, Sean; WO2012/74999; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 103-50-4, name is Benzyl ether, 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 103-50-4, 103-50-4

General procedure: To a stirred solution of ether (1.0 mmol) in AcOH (6 mL), was added 30 mol % of BF3¡¤Et2O followed by the addition of cyanamide (1.0 mmol). The reaction mixture was refluxed at an elevated temperature (40-50 C) till the completion of the reaction as monitored by TLC. Upon complete consumption of the cyanamide, the reaction medium was diluted with EtOAc (15 mL). The organic layer was washed with water followed by 5% NaHCO3 (2 ¡Á 5 mL), water (2 ¡Á 5 mL), and brine (5 mL). The organic layer was then dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo to afford the crude which was then purified through silica gel column chromatography (30-40% EtOAc/hexane).

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, Benzyl ether, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Panduranga, Veladi; Basavaprabhu; Sureshbabu, Vommina V.; Tetrahedron Letters; vol. 54; 8; (2013); p. 975 – 979;,
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