Month: June 2021

Related Products of 20781-20-8, 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 20781-20-8 as follows.

To a solution of ethyl 4,6-dichloronicotinate (15 g, 68 mmol), TEA (8.25 g, 81.5 mmol) in MeCN (200 mL) at 0 C was added (2,4-dimethoxyphenyl)methanamine (12 g, 71 mmol) over 0.5 h. The mixture was stirred at rt for 1 6h and then concentrated. The residue was diluted withEtOAc, washed with water, brine, dried over Na2SO4 and then concentrated to afford ethyl 6-chloro-4-((2,4-dimethoxybenzyl)amino)nicotinate (22 g, 92%) as a yellow solid.

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRINCIPIA BIOPHARMA, INC.; VERNER, Erik; BRAMELD, Kenneth Albert; WO2015/120049; (2015); A1;,
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Electric Literature of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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: A mixtureof 4,5-dichloroimidazole (Ia) (1.37 g, 10 mmol)and finely ground KOH (10 mmol, taking intoaccount the 85% content) in DMSO (7 mL) wasstirred at 35 C for 15 min, followed by the addition of2-aryloxybromide (11 mmol) at such a rate that thereaction temperature did not exceed 50C. The reactionoccurred for 30 min at 45C. After cooling, water(40 mL) was gradually added, and the resulting voluminousprecipitate of 1-aryloxyethyl-substitutedimidazoles (IIf)-(IIn) were filtered and washed with5% KOH (2 mL) and water.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Bromoethoxy)-4-fluorobenzene, its application will become more common.

Reference:
Article; Kovalenko; Divaeva; Zubenko; Morkovnik; Drobin; Fetisov; Bodryakov; Dorofeenko; Russian Journal of Bioorganic Chemistry; vol. 42; 5; (2016); p. 551 – 559; Bioorg. Khim.; vol. 42; 5; (2016); p. 608 – 616,9;,
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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. 103-50-4, name is Benzyl ether, A new synthetic method of this compound is introduced below., Recommanded Product: 103-50-4

6-{2-[2-(2-{2-[2-(2-hydroxyethoxy) ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester (4). Substantially monodispersed benzyl ether 3 (1.03 g, 2.0 mmol) was dissolved in 25 ml ethanol. To this solution was added 270 mg 10% Pd/C, and the mixture was placed under a hydrogen atmosphere and stirred for four hours, at which time TLC showed the complete disappearance of the starting material. The reaction mixture was filtered through Celite 545 to remove the catalyst, and the filtrate was concentrated in vacuo to yield the monodispersed compound 4 as a clear oil (0.67 g, 79%). FAB MS: m/e 425 (M+H), 447 (M+Na).

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; Soltero, Richard; Radhakrishnan, Balasingam; Ekwuribe, Nnochiri N.; US2003/87808; (2003); A1;,
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These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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 3-Benzyloxyaniline

General procedure: [0158]7?c?3). Compound Ta or Tv (0.02 minol) dissolved in 0.5 ml.. of DMF was added to a solution of corresponding amines (0.04 mmol), HOB?I? (3.06 rng, 0.02 rnmol), [II3TU (7.5 mg, 0.02 inmol), and D1PEA (5.16 1±L, 0.04 mmol) in I mE of DMF. The mixture was stirred under room temperature for 4 hours. This crude product was purified by Pre-HPLC to give Ta?I to 7?a-3 and 7?c?l to 7?c?3.[0159] 2-(-ft3-(benzyloxy)phenyl)amino)-4-oxobntyfl-6-hydroxy-3-iodo-l-methyl-lH-indole-5-carboxylic acid (Ta-i, L89M52). White solid (5.4 tug,46percent): H NMR (500 MHz, DM80): iS 13.68 (s, IN), 11.27(s, 111), 9.91 (s, 111), 7.70(5, 1 H ), 7.45?7.3 1 (m, 611), 7. 18 (m, 1K), 7.10 (in, I H), 6.96 (s, 1 K), 6.69 (in, 111).5.05 (s. 211), 3.73 (a, 3K), 2.65 (nt 2H), 2.39 (in, 2H), 1.87 (in, 2H); LC-MS (ESI):607.0 (M±Na, 582.8 (M-H)?; Purity: >95percent WV, A 254 urn).

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

Reference:
Patent; INDIANA UNIVERSITY RESEARCH & TECHNOLOGY CORPORATION; ZHANG, Zhong-Yin; ZENG, Li-Fan; WO2014/176488; (2014); A1;,
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Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, 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

Intermediate 67: Mixture of (trans)-N-{2-amino-4-r(trifluoromethyl)oxylphenyl)-2-oxo-3-(3- pyridinyl)-1-oxa-3-azaspiror4.5ldecane-8-carboxamide and (trans)-N-{2-amino-5- [(trifluoromethvDoxyiphenvD^-oxo-S-O-pyridinvD-i-oxa-S-azaspiroK.deltaidecane-delta- carboxamide; Lithium (trans)-2-oxo-3-(3-pyridinyl)-1-oxa-3-azaspiro[4.5]decane-8-carboxylate (Intermediate 66, 75 mg, 0.251 mmol) and EDC (77 mg, 0.401 mmol) were suspended in pyridine (2 ml) and stirred for 30 min. 4-[(trifluoromethyl)oxy]-1 ,2-benzenediamine (Intermediate 32, 72.2 mg, 0.376 mmol) was then added and the resulting dark solution was stirred overnight at r.t. Solvent was removed under vacuum, taken up with DCM (20 ml) and washed with saturated NaHCO3 solution (2X5 ml). The organic phase was concentrated under vacuum to afford a crude oil. The crude was purified by flash chromatography on Biotage SP1 (25+M column, NH cartridge) eluting in gradient with CyclohexaneEtOAc. The title compound was eluted with 100% EtOAc and recovered as colourless solid (60 mg) as mixture of regioisomers with unknown ratio. 1 H-NMR (400 MHz, CD3OD): delta 8.88 (br s, 2H), 8.34-8.32 (m, 2H), 8.13 (dq, 2H), 7.50-7.45 (m, 2H), 7.18-7.14 (m, 2H), 6.97-6.95 (m, 1 H), 6.75-6.73 (m, 1 H), 6.58-6.53 (m, 2H), 3.74 (s, 4H), 2.68-1.68 (m, 18 H); UPLC-MS: 0.60 min, mz 226 [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 658-89-9, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
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Reference of 366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, 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.

Was added in a 500 mL reaction flask3-fluoro-4-methoxyaniline(30 g, 0.21 mol) and dichloromethane(100 mL).The ice bath was cooled to below 5 ° C,Acetic anhydride was slowly added dropwise(22 mL, 0.23 mol),The temperature of the reaction solution was controlled at 30 ° C or lower,About 1 hour period.Remove the ice bath,After stirring at room temperature for 5 hours,N-Hexane (300 mL) was added to the reaction solution,A large number of solid precipitation.After stirring for 1 hour,The filter cake was washed with n-hexane,30 degrees vacuum drying,To give the title compound (whiteColor solid powder, 28 g, 72percent).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang, Ruihao; (36 pag.)CN105949178; (2016); A;,
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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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C18H21NO4

In a three-necked flask equipped with a stirrerDOTA (20 g, 0.05 mol),Thionyl chloride (200 ml)Stirring, heating reflux 4h,After cooling, the dichlorosulfone liquid was distilled off under reduced pressure,Then, 100 ml of dry THF was added, the solvent was distilled off under reduced pressure,To give solid acid chloride.The resulting solid acid chloride was dissolved in 250 ml of dry dichloromethane,Adding 20 ml of diisopropylethylamine,Stir,Ice bath to join(Z)-1- (3,4,5-trimethoxyphenyl) -2- (3-hydroxy-4-methoxyphenyl) ethylene (4 g, 0.0125 mol), the ice bath was removed and the temperature was gradually raised to 30 C. 3h, TLC tracking.After the reaction, add ice water 100ml, stirring 30min, vacuum distillation of organic solvents. In the aqueous phase with concentrated hydrochloric acid to adjust the pH to 2, a solid precipitation, filtration to obtain a white solid,Recrystallization from an ethanol-water solution gave 22.8 g of the desired product in 65% yield.

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; Zhejiang Dade Pharmaceutical Group Co., Ltd.; Wang Jianping; Wang Jianguo; (23 pag.)CN104447598; (2017); B;,
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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. 10541-78-3, name is 2-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Methoxy-N-methylaniline

General procedure: The N-methyl aniline intermediates were prepared according to the method in the literature. To a solution of sodium 3,4-dioxo-3,4-dihydronaphthalene-1-sulfonate (2) (130 mg, 0.5 mmol) in water (15 mL), N-methyl aniline intermediate (0.55 mmol) was added. The reaction mixture was stirred at room temperature for 3 to 20 h (TLC monitoring). For the preparation of compounds 3, the solvent was removed in vacuum, and the residue was purified by column chromatography to give the target products. For the preparation of compounds 4, the precipitate produced was filtered, and the residue was crystallized from EtOH to give compounds 4 as red solids.

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 10541-78-3.

Reference:
Article; Yang, Honghao; An, Baijiao; Li, Xingshu; Zeng, Wei; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3057 – 3063;,
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Reference of 366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, 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.

To cyanuric chloride (0.180 g,1 mmol) in 1,4-dioxane (1 mL) at about- 10 to-20 C was addedN, N-diisopropylethylamine (DIEA) (0.19 mL,lmmol) in CH3CN (1 mL) and3-fluoro-p-anisidine (0.14 g, 1 mmol) inCH3CN(1 mL) and stirred for about1 hour. The reaction mixture was then stirred at room temperature for about I hour. Then a solution of cycloheptylamine (0.13mL,1 mmol) and DIEA (0.19 mL, 1 mmol) inCH3CN (0.5 mL) was added and the reaction mixture was stirred overnightat rt. Then, N-methyl-4 (methylamino) piperidine (0.15 mL,1 mmol) and DIEA (0.19 mL,1 mmol) inCH3CN (0.5 mL) were added and the reaction mixture was refluxed overnight. The reaction mixture was worked-up using saturated sodium bicarbonate, and brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 90: 9: 1 dichloromethane: methanol:conc. ammonium hydroxide) to give 158 (0.130 g, 28percent) ; TLC (silica gel, 90: 9 : 1,CH2CI2, CH30H, conc.NH40H), Rf 0.26) ;1H NMR (600MHz, CDC13, 55 C)8 7.74 (br s, 1H), 6.94 (br s, 1H), 6.81-6. 84(m, 2H), 4.83 (br resonance, 1H), 4.55 (s,1H), 3.98 (s,1H), 3.82 (s,3H), 2.97 (s, 3H), 2.94 (br d,J=11. 9 Hz, 2H), 2.29 (s, 3H), 2.06-2. 10(m, 2H), 1.93-1. 97(m, 2H), 1.84-1. 90(m, 2H), 1.44-1. 66(m, 12H). Compound 159 was’isolated as a by-product (55 mg) by column chromatography (silica gel, 90: 9: 1 dichloromethane: methanol:conc. ammonium hydroxide); TLC (silica gel, 90: 9: 1,CH2C12, CH30H, conc.NH40H), Rf 0.1) ; HPLC: Inertsil ODS-3V C18, 40: 30: 30 [KH2PO4(0. 01 M, pH 3.2) :CH30H : CH3CN], 264nm, Rt 8.3 min, 93.5percent purity; MS(ESp : m/z 443 (M+H, 100).

Statistics shows that 3-Fluoro-4-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 366-99-4.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); 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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H13NO

General procedure: A 25 mL round bottomed flask was charged with N,N-dialkyl-aniline (0.5 mmol), 2-naphthol (0.5 mmol) and acetonitrile (3 mL), followed by 10 mg of Ce-MCM-41 and TBHP (2 equiv.) via syringe. The mixture was heated to 60 C and stirred for 3 h in open air. After completion of the reaction, as judged by TLC, the solution was cooled and the catalyst was removed by filtration. The resulting crude mixture was gently evaporated under reduced pressure and purified by column chromatography using silica gel and a mixture of hexane and ethyl acetate as the eluent.

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 701-56-4.

Reference:
Article; Akondi, Adinarayana Murthy; Trivedi, Rajiv; Sreedhar, Bojja; Kantam, Mannepalli Lakshmi; Bhargava, Suresh; Catalysis Today; vol. 198; 1; (2012); p. 35 – 44;,
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