Tag: M.W=100-200

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 7664-66-6 as follows. name: 4-Isopropoxyaniline

General procedure: 3-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the appropriate alkoxyaniline (5.3 mmol) were suspended in dry chlorobenzene (25 mL). Phosphorous trichloride (0.23 mL, 2.7 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure and the solid residue washed with 50 mL of 2 M HCl. The crude product was recrystallized from aqueous ethanol.

According to the analysis of related databases, 7664-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gonec, Tomas; Zadrazilova, Iveta; Nevin, Eoghan; Kauerova, Tereza; Pesko, Matus; Kos, Jiri; Oravec, Michal; Kollar, Peter; Coffey, Aidan; O’Mahony, Jim; Cizek, Alois; Kralova, Katarina; Jampilek, Josef; Molecules; vol. 20; 6; (2015); p. 9767 – 9787;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (2,4-Dimethoxyphenyl)methanamine

1-(2,4-Dimethoxyphenyl)methanamine (23 g, 140 mmol) was added to a solution of C6 (20 g, 91 mmol) in methanol (275 mL). The reaction mixture was stirred at room temperature (20 C) for 24 hours, whereupon it was cooled to -78 C and treated in a drop-wise manner with lithium borohydride (2 M solution in tetrahydrofuran; 46.0 mL 92.0 mmol). The reaction mixture was allowed to slowly warm to room temperature, andwas then stirred at room temperature overnight. This was combined with a similar reaction mixture that employed C6 (16.18 g, 73.5 mmol) and concentrated in vacuo. The residue was mixed with saturated aqueous sodium bicarbonate solution (300 mL) and water (200 mL), and extracted with ethyl acetate (4 x 200 mL). The combined organic layers were dried over sodium sulfate, filtered, concentrated under reducedpressure, and purified via chromatography on silica gel (Gradient: 0% to 9% methanolin dichloromethane) to provide the product as a light yellow oil. Combined yield: 52.0 g,140 mmol, 85%. LCMS m/z 371.9 [M+H]. 1H NMR (400 MHz, CDCI3) 7.38-7.25 (m,5H), 7.12 (d, J=8.0 Hz, 1H), 6.46 (d, half of AB quartet, J=2.5 Hz, 1H), 6.43 (dd, half ofABX pattern, J=8.O, 2.5 Hz, 1 H), 4.58 (AB quartet, JAB= 12.0 Hz, IIVAB=23.2 Hz, 2H),4.07 (ddd, J=1 1.5, 4.5, 1.5 Hz, 1 H), 3.81 (5, 3H), 3.80 (5, 3H), 3.75 (5, 2H), 3.59-3.39(m, 4H), 2.75-2.65 (m, 1H), 1.91-1.80 (m, 2H), 1.48-1.35 (m, 1H), 1.23-1.12 (m, 1H).

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; PFIZER INC.; BRODNEY, Michael Aaron; CHAPPIE, Thomas Allen; CHEN, Jinshan Michael; COE, Jotham Wadsworth; COFFMAN, Karen Jean; GALATSIS, Paul; GARNSEY, Michelle Renee; HELAL, Christopher John; HENDERSON, Jaclyn Louise; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G.; MARTINEZ-ALSINA, Luis Angel; PETTERSSON, Martin Youngjin; REESE, Matthew Richard; ROSE, Colin Richard; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; WARMUS, Joseph Scott; ZHANG, Yuan; (193 pag.)WO2018/163066; (2018); A1;,
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Synthetic Route of 39538-68-6, 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 39538-68-6 as follows.

To a solution of 3a (550 mg,4 mmol) in 3 mL concentrated HCl at 0 C was added NaNO2(320 mg, 4.6 mmol; dissolved in 5 mL H2O), and the mixture was stirred at 0 C for 1 h. A solution of KI (950 mg, 5.7 mmol; dissolvedin 10 mL H2O) was added dropwise at 0 C, and the mixture was slowly warmed up to room temperature overnight with stirring. The mixture was extracted with ether and the combined organic layers were washed with brine, dried over anhydrous MgSO4, and evaporated under reduced pressure. The residue was purified by silica gel flash chromatography (hexane as eluent) to give the titled product as colorless oil (0.826 g, 84% yield): 1H NMR (400 MHz, CDCl3) delta 7.62 (d, J=7.9 Hz, 1H), 6.65 (s, 1H), 6.55 (d, J=7.9 Hz, 1H), 3.87 (s, 3H), 2.33 (s, 3H).

According to the analysis of related databases, 39538-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Muppidi, Avinash; Doi, Kenichiro; Ramil, Carlo P.; Wang, Hong-Gang; Lin, Qing; Tetrahedron; vol. 70; 42; (2014); p. 7740 – 7745;,
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Synthetic Route of 3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Step 8B: Compound 8-2; To a flask containing (R)-1-{4-[2-((S)-l-amino-2-methyl-propyl)-6-fluoro-phenyl]- piperazin-l-yl}-3- (4-chloro-phenyl)-2-methyl-propan-l-one (43 mg, 0. 10 mmol) and (2,2- diethoxy-ethyl) -dimethyl-amine (100 pL, 0.50 mmol), TFA (30011L, 4.0 mmol) was added via syringe. After-5 min. , NaCNBH3 (95 mg, 1.5 mmol) was added and the resulting mixture was heated to 120 °C overnight. The resulting brown reaction mixture was concentrated in vacuo and purified via preparative HPLC/MS to furnish 8-2 (3.8 mg, 0.006 mmol, 6percent) as the TFA salt. LCMS-tR (method 4) 1.596 min. m/z 502.8 (M+ + H+).

The chemical industry reduces the impact on the environment during synthesis 2,2-Diethoxy-N,N-dimethylethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/42516; (2005); A2;,
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Reference of 7664-66-6, The chemical industry reduces the impact on the environment during synthesis 7664-66-6, name is 4-Isopropoxyaniline, I believe this compound will play a more active role in future production and life.

4-Isopropoxy-phenylamine (1.52 g, 10 mmol) in CH2Cl2 (10 mL) was slowly added to 1,1′-carbonyldiimidazole (CDI, 1.64 g, 10 mmol) in CH2Cl2 (5 mL) at 0 C. After stirring at room temperature for 1 h, 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.05 g, 10 mmol) in CH2Cl2 (5 mL) was added and the mixture was kept stirring at room temperature overnight. It was quenched with water and extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4 and evaporated. A portion of the BOC-protected product (0.35 g, 0.93 mmol) was re-dissolved in CH2Cl2 (5 mL). To this solution was added 1 mL of trifluoroacetic acid and the resulting mixture was stirred at room temperature for 1 h. The organic solvents were removed in vacuo and the crude material was neutralized with 2 M NH3 in MeOH. After evaporation of the solvents, the crude residue was purified by flash column chromatography on silica gel (5% MeOH/CH2Cl2) to afford the product as a light brown solid (250 mg, 97%). 1H NMR (CDCl3) delta 7.26 (m, 2H), 6.84 (d, J=8.70 Hz, 2H), 6.49 (br, 1H), 4.88 (m, 1H), 4.48 (sep, J=6.0 Hz, 1H), 3.12 (m, 2H), 2.83 (m, 2H), 2.04 (m, 2H), 1.71 (m, 2H), 1.31 (d, J=6.0 Hz, 6H); LC/MS (ESI) calcd for C15H23N2O3 (MH)+ 279.2, found 279.3.

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

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281700; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, 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 60792-79-2, name: 2,2′-Oxybis(ethylamine) dihydrochloride

To a solution of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.55 g, 1.95 mmol) in 1-methyl-2-pyrrolidone (40 mL) bis-(2-aminoethyl)-ether dihydrochloride (2.1 g, 11.9 mmol, 6eq.) and DBU (3.49 mL, 23.4 mmol, 12 eq.) added and the reaction mixture was stirred at 110 C. for 18 hours. The reaction mixture was then diluted with water (70 mL) and the pH was adjusted to 11 and extracted with CH2Cl2 (9*40 mL). Water layer was then acified with H2SO4 to pH 6.8, extracted with 50 mL of CH2Cl2 and then evaporated in vacuum. Crude product was diluted in 2-propanol (60 mL), stirred at 82 C. for 20 minutes and filtrated. Precipitate was pure salt (Na2SO4). 2-Propanol was evaporated in vacuum and product was purified by column chromatography (fraction, eluent: CH2Cl2-MeOH-NH3-CH3CN=4:4:2:1) yielding 0.5 g of title compounds as a mixture of chloro and fluoro derivatives in ratio 3:1 MS (ES+) m/z: [MH]+=365.8 (A) (75%) MS (ES+) m/z: [MH]+=349.4 (B) (25%).

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; Pliva-Istrazivacki Institut d.o.o.; Glaxo Group Limited; US2006/258600; (2006); A1;,
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Related Products of 22483-09-6, These common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, 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.

100 g of aminoacetaldehyde dimethyl acetal and 146 g of benzaldehyde are added to 2.5 liters of toluene, heated to reflux for 16 hours, and concentrated.The residue was dissolved in 1.8 L of methanol, 45 g of sodium borohydride was slowly added in portions, and the mixture was stirred at room temperature for 5 hours.Saturated ammonium chloride solution was added and extracted with ethyl acetate, followed by liquid separation, drying,Concentration gave 162 g of N-benzyl-2,2-dimethoxyethanamine and the crude product was used in the next reaction without purification.

Statistics shows that 2,2-Dimethoxyethanamine is playing an increasingly important role. we look forward to future research findings about 22483-09-6.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (6 pag.)CN107778208; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 454-90-0, name is 3-(Trifluoromethyl)anisole, 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 454-90-0, Quality Control of 3-(Trifluoromethyl)anisole

In each of the examples in Table 3A, the substrate is reacted with the base in THF to form a metallic organoborate intermediate under the temperature and time conditions specified in Table 3A. The metallic organoborate intermediate is then reacted with the electrophile, E, in THF to form the functionalized products 11b to 11g under the following conditions:Similarly, the substituted arenes 10b-d reacted with 2b (25 C, 0.5-12 h) affording the corresponding borate which lead after subsequent cross-coupling (ZnCl2 (10 mol%), Pd(OAc)2 (3 mol%), S-Phos (6 mol%), 65 C, 1 h) with 12 (0.8 equiv) to the biphenyl derivatives llb-d in 75-95% yield (Table 3A, entries 2-4). For example, tmpBEtyMgCl LiCl (2.2 mL, 1.0 M in THF, 2.2 mmol) was added dropwise at 25 C to a solution of 3,5-(trifluoromethyl)anisole (10b; 352 mg, 2.0 mmol) in THF (2 mL) in a flame-dried and Argon-flushed Schlenk-tube equipped with septum and magnetic stirring bar. After stirring for 1 h at 25 C, ZnCl2 (0.2 mL, 1 M in THF, 10 mol%), Pd(OAc)2 (14 mg, 3 mol%), S-Phos (25 mg, 6 mol%) and ethyl 4-iodobenzoate (12; 441 mg, 1.6 mmol) were added followed by continuously stirring for 1 h at 65 C. After cooling to 25 C, the reaction mixture was diluted with Epsilon2Omicron (5 mL) and quenched with sat. NH4C1 (aq.) (5 mL). The aqueous layer was extracted with CH2CI2 (3x 15 mL). The combined organic phases were dried over Na2SC>4 and the solvent was removed under vacuum. Flash column chromatography (pentane-Et20, 9: 1) afforded lib (492 mg, 95%) as a pale yellow solid.

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; HAAG, Benjamin; WO2012/85169; (2012); 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, Formula: C7H7F2NO

Example 2 3- { [4- (DIFLUOROMETHOXY) PHENYL] AMINO}-1- (2-METHOXYETHYL)-4-PHENYL-LH-PYRROLE-2, 5- dione 3-CHLORO-1-(2-METHOXYETHYL)-4-PHENYL-LH-PYRROLE-2, 5-dione (0.13 mmol, 36 mg) AND 4- difluoromethoxyaniline (0.28 mmol, 45 mg) were dissolved in DMF (1 mL). The mixture was heated in a microwave reactor at 150C for 20 min.. After cooling, the reaction mixture was purified by HPLC (95% 0. 1M ammonium acetate buffer: 5% CH3CN No. 100% CH3CN) to give 13 mg (24%) of the title COMPOUND. 1H NMR (400 MHz, CDC13) : 8 7.25 (bs, 1H), 7.19-7. 08 (m, 3H), 7.02-6. 97 (m, 2H), 6.81-6. 75 (m, 2H), 6.66-6. 60 (m, 2H), 6.36 (t, J=74.0 Hz, 1H), 3. 83 (t, J=5.7 Hz, 2H), 3.63 (t, J=5.7 Hz, 2H), 3. 38 (s, 3H)

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

Reference:
Patent; ASTRAZENECA AB; WO2005/5417; (2005); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 74654-07-2

Example 58A tert-Butyl [(trans-4-{[(2S)-3-[4′-({2-[2-(2-methoxyethoxy)ethoxy]ethyl}carbamoyl)-2′-methylbiphenyl-3-yl]-1-oxo-1-{[4-(1H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate 3′-[(2S)-2-{[(trans-4-{[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-oxo-3-{[4-(1H-tetrazol-5-yl)phenyl]amino}propyl]-2-methylbiphenyl-4-carboxylic acid and 2-[2-(2-methoxyethoxy)ethoxy]ethanamine (29 mg, 0.17 mmol) were dissolved in tetrahydrofuran (4 ml), N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (67 mg, 0.17 mmol) and N,N-diisopropylethylamine (23 mg, 0.17 mmol) were added and the mixture was stirred at RT overnight. Subsequently, the mixture was concentrated and the residue was purified chromatographically by HPLC (Method 10). This gave 53 mg (44% of theory) of the title compound. LC-MS (Method 4): Rt=1.17 min; MS (ESIpos): m/z=827.6 [M+H]+.

The synthetic route of 74654-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHN, Ulrike; ELLERMANN, Manuel; STRASSBURGER, Julia; WENDT, Astrid; ROeHRIG, Susanne; WEBSTER, Robert Alan; SCHMIDT, Martina Victoria; TERSTEEGEN, Adrian; BEYER, Kristin; SCHAeFER, Martina; BUCHMUeLLER, Anja; GERDES, Christoph; SPERZEL, Michael; SANDMANN, Steffen; HEITMEIER, Stefan; HILLISCH, Alexander; ACKERSTAFF, Jens; TERJUNG, Carsten; (163 pag.)US2016/244437; (2016); A1;,
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