Category: ethers-buliding-blocks

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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., 366-99-4

Example 104 Synthesis of 6-Chloro-N,N’-bis-(3fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine (E15) To 124 (1.09 g, 3.5 mmol) dissolved in acetone (25 mL) was added 3-fluoro-p-anisidine (0.54 g, 3.5 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.4 mL, 3.5 mmol) and water (3.5 mL). The reaction mixture was stirred and heated at reflux for 3 hours. The reaction mixture was extracted three times using dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was filtered, concentrated in vacuo, and the resulting solid was dried overnight under vacuum to yield white solid (E15) (1.332 g, 97percent); mp 194¡ã C.; HPLC: Inertsil ODS 3V C18, 40:30:30 v:v:v [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 33.2 min, 97.6percent purity; MS (TOF ES+) m/z 396 (35.0); 394 (M+H, 100).

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; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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60792-79-2, A common compound: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A suspension of 0.2 M 2,2′-oxydiethylamine dihydrochloride (0.167 gm, 0.92 mmole) and 0.4 M DIEA (0.40 ml, 2.3 mmole) in 2.5 DMF was added to 4-amino-1,8-naphthalic anhydride (0.067 gm, 0.30 mmole) and heated at 170 C with microwave treatment under nitrogen for 10 minutes. The mixture was cooled, concentrated under vacuum, and purified by preparatory HPLC to give N-aminoethylethoxy-4-amino- EPO 1,8 naphthalimide 8. MS m/z 300 (M + H)+

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, 2,2′-Oxybis(ethylamine) dihydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; WO2006/60533; (2006); A2;,
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Adding a certain compound to certain chemical reactions, such as: 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)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 349-55-3, 349-55-3

Example 39 Synthesis of 3,5-Diamino-4-[(3-methoxy-5-trifluoromethylphenyl)-hydrazono]pyrazole This compound was prepared using 134 mg (0.5 mmol) of 2-[(3-methoxy-5-trifluoromethylphenyl)hydrazono]malononitrile, which was derived from 3-methoxy-5-trifluoromethylaniline (191 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Very little solid had formed after heating the reaction at 75 C. for 1 hr, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to room temperature and the solvent was evaporated. The residue was dissolved in ethyl acetate and then precipitated by the addition of hexanes. The resulting solid was isolated by filtration and dried to yield 10 mg (7%) of the title compound as a yellow solid.

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, 3-Methoxy-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kinetek Pharmaceuticals, Inc.; US6436915; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-methoxybenzene, 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 321-28-8, 321-28-8

General procedure: To a 5 mL screw-capped vial equipped with a 15¡Á10 mm spinvane triangular-shaped Teflon stirbar, simple arene 1(0.5 mmol), saccharin (1.0 mmol), Selectfluor (1.0 mmol), K2CO3 (1.0 mmol) and CuCl (0.1 mmol) were added in nitromethane (3.0 mL). The mixture was sealed with aTeflon-lined cap and stirred at 90 C for 6.0 h (monitoredby TLC), extracted with dichloromethane (5¡Á3 mL), and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by flash silica gel column chromatography to give aromatic amine 2. The characterizations of aromatic amines 2 and 4 were listed in the Supporting Information online.

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, 1-Fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Kai; Li, Yan; Zhang, Qian; Science China Chemistry; vol. 58; 8; (2015); p. 1354 – 1358;,
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Adding a certain compound to certain chemical reactions, such as: 4179-19-5, name is 3,5-Dimethoxytoluene, 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 4179-19-5, 4179-19-5

Into a 500-mL 3-necked round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-dimethoxy-5-methylbenzene (5 g, 32.85 mmol, 1.00 equiv) in dichloromethane (150 mL). This was followed by the addition of sulfuroyl dichloride (8.869 g, 65.71 mmol, 2.00 equiv) dropwise with stirring at 00 C. Theresulting solution was stirred overnight at room temperature. The pH value of the solution was adjusted to 8 with sodium carbonate (sat. aq.). The resulting solution was extracted with dichloromethane, and the combined organic layers were concentrated under vacuum. The resulting mixture was washed with hexane to give 5.36 g (74%) of 2,4-dichloro-1,5-dimethoxy- 3-methylbenzene as a white solid.

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, 3,5-Dimethoxytoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth A.; VERNER, Erik; WO2014/182829; (2014); A1;,
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A common compound: 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 363-47-3

Example 19 N-(3,5-difluoro-4-methoxyphenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0299) To a mixture of 3,5-difluoro-4-methoxyaniline (54 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (46 mg). 1H NMR (300 MHz, DMSO-d6) delta3.86 (3H, s), 4.15 (2H, s), 6.88 (1H, d, J = 6.8 Hz), 7.25 (1H, dd, J = 9.0, 6.8 Hz), 7.35 (2H, d, J = 10.5 Hz), 7.55 (1H, d, J = 9.0 Hz), 7.62 (1H, d, J = 1.1 Hz), 7.85 (1H, s), 10.66 (1H, s).

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, 363-47-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
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1515-81-7, 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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), thiol (1.0 mmol), p-methoxybenzylmethyl ether (167 mL,167 mg, 1.10 mmol), TMSOTf (271 muL, 333 mg, 1.50 mmol), anddiisopropylethylamine (244 muL, 181 mg, 1.40 mmol). The homogenous mixture was stirredovernight and then passed through a column of silica (2 cm x 1 cm) with Et2O.The solvent was removed in vacuo and the residue was purified by columnchromatography (0-2% EtOAc/hexanes).

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:
Article; Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; Confair, Danielle N.; Tetrahedron Letters; vol. 55; 37; (2014); p. 5213 – 5215;,
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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. 111-95-5, name is Bis(2-methoxyethyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 111-95-5

In a 100 ml eggplant type flask, 3.6 ml (25 mmol) of bis (2-methoxyethyl) amine,3.2 g (25 mmol) of phloroglucinol and 30 ml of THF were added and stirred. After 48 hours,The reaction was confirmed by TLC (SiO 2, developing solvent hexane: acetone = 1: 1), followed by extraction with chloroform, and the solvent was distilled off under reduced pressure to obtain a black viscous substance (yield 5.1 g, yield 86 %).

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Satoru: Yamagata University; Kido Junji; Sasabe Hisa Hiroshi; Sasaki Isamu; (15 pag.)JP6281975; (2018); B2;,
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These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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. 20781-20-8

Intermediate 3C:; [00197] To Intermediate 3B (3.0 g, 11.99 mmol) in toluene (18 mL) was added (2,4-dimethoxyphenyl)methanamine (2.476 mL, 16.48 mmol). The mixture was stirred at 125 0C (oil bath) for 3.5 h. The color changed from deep red to yellow. After the mixture cooled to rt, it was triturated with EtOAc/hexanes (1 : 2) and left standing overnight. The yellow precipitate was collected by filtration to give Intermediate 3C (3.92 g, 96% yield).

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 20781-20-8.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
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22236-10-8, 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 22236-10-8 as follows.

2-Chloro-N-(4-(difluoromethoxy)phenyl)acetamide (Compound 39): To a solution of 4-(difluoromethoxy)aniline (0.078 ml, 0.628 mmol) and Triethylamine (0.131 ml, 0.943 mmol) in DCM at 0 C., was added 2-chloroacetyl chloride (0.060 ml, 0.754 mmol). The mixture was stirred at RT for 2 h. Solvent was removed and the crude was purified by combiflash chromatography (0-30% EtOAc-Hexanes) to afford 2-chloro-N-(4-(difluoromethoxy)phenyl)acetamide (110 mg, 0.467 mmol, 74.3% yield) as a pale orange solid. 1H-NMR (400 MHz, CDCl3) delta ppm 8.24 (brs, 1H), 7.55 (dd, 2H, J=2 Hz, J=4 Hz), 7.13 (d, 2H, J=8 Hz), 6.48 (t, 1H, J=71.5 Hz), 4.20 (s, 2H); ESI-MS: m/z 235.86 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 22236-10-8, and friends who are interested can also refer to it.

Reference:
Patent; Stingray Therapeutics, Inc.; The University of Utah; Vankayalapati, Hariprasad; Liu, Xiaohui; Ramamoorthy, Gurusankar; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (59 pag.)US2019/31655; (2019); A1;,
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