Month: June 2021

658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, 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. HPLC of Formula: C7H7F3N2O

To a stirred solution of compound AW (4.0 g, 20.83 mmol) in CH3OH (40 mL) was added 2-oxoacetic acid (2.3 mL, 20.83 mmol) at 0 C. The resulting reaction mixture was allowed to warm to RT and stirred for 24 h. After the consumption of starting material (by TLC), the reaction mixture was diluted with H2O (50 mL) and stirred for 5 min. The solid precipitated was filtered and washed with H2O (3×50 mL). The crude solid was purified by silica gel column chromatography (eluting with 30% EtOAc/hexane) to afford compound AX (1.4 g, 6.08 mmol, 29.8%) as pale-yellow solid. 1H NMR (500 MHz, DMSO-d6): delta 12.6 (br s, 1H), 8.25 (s, 1H), 7.78 (s, 1H), 7.60 (d, J=7.0 Hz, 1H), 7.04 (d, J=8.5 Hz, 1H). MS (ESI): m/z 230 [M+H]+.

The synthetic route of 658-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
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Reference of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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 mixture of 0.6 mmol of quinomethane 1a-1c and 0.6 mmol of 3,3-diethoxypropan-1-amine (2) or 4,4-diethoxybutan-1-amine (3) in 1 mL of 1,4-dioxane was stirred for 2-3 h at room temperature under argon. When the reaction was complete, the solvent was removed under reduced pressure (water-jet pump), and the residue was washed with hexane and dried in a vacuum (oil pump) until constant weight.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Article; Vagapova; Amirova; Burilov; Pudovik; Sinyashin; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1268 – 1271; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1294 – 1297,4;,
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Adding a certain compound to certain chemical reactions, such as: 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, 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 60789-54-0, name: ((4-Bromobutoxy)methyl)benzene

2-(4-benzyloxy)butyl-propanedioic acid, diethyl ester 19 To a warm solution of sodium (49.5 g, 2.15 mol) in 1 L abs. ethanol there is added diethyl malonate (325 mL, 2.11 mol). The solution is warmed up to 50 C. and crude bromide 18 (410 g, 1.68 mol) is added over a 30 m period. The mixture warms up to 65 C. and is then heated under reflux for 1 h. Most of the solvent is evaporated and to the residue there is added 1 L toluene and 500 mL water. The layers are separated and the organic layer is washed with 2*750 mL water, then dried and evaporated. The residue is purified by bulb-to-bulb distillation to afford 410 g of 19 (1.273 mol, 76%) with bp 170 C. (0.2 mmHg). This product is used as such in the next step. 1 H-NMR (CCl4): delta 1.0-2.0 (m) and 1.2 (t) (12H), 3.2(t, 1II), 3.4 (t, 2H), 4.0 (q, 4H), 4.3 (s, 2II), 7.2 (s, 5H).

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; The Horticulture and Food Research Institute of New Zealand Limited; US5677432; (1997); A;,
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Related Products of 148583-65-7,Some common heterocyclic compound, 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, molecular formula is C9H12FNO, 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 1: Phosgene (20% in toluene; 63 mL, 118.2 mmol, 2 equiv) was cooled to – 10 C (ice/MeOH) under argon. Then 4-fluoro-2-isopropoxybenzenamine (10.0 g, 59.1 mmol, 1 equiv) was added drop wise, and the reaction mixture was stirred at -10 C for 15 min then heated to 90 C for 3 h under argon. After cooling, the reaction mixture was evaporated to dryness, and the crude 4-fluoro-l-isocyanato-2-isopropoxybenzene was dried in vacuo.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); A1;,
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Electric Literature of 321-28-8, 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 3-fluoro-4-methoxybromobenzene Into a flask of 5 l were charged 384 g (3.04 mol) of 2-fluoroanisole and 2.5 l of chloroform, to which was added dropwise 504 g (3.16 mol) of bromine over about 3 hours while cooling on an ice water bath at 10 C. The resulting mixture was stirred at room temperature over a night and heated under reflux for 8 hours. After the air cooling, the product was added with 1 l of water and 50 g of sodium bisulfite and sufficiently shaken to separate into two layers. The resulting organic layer was washed with an aqueous solution of 5% sodium hydrogen carbonate and further with 1 l of water and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and distilled under a reduced pressure (4 mmHg, bp: 93-96 C.) to obtain 585 g (yield: 94%) of 3-fluoro-4-methoxybromobenzene.

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:
Patent; Nippon Mining Co., Ltd.; US5098602; (1992); A;,
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Synthetic Route of 162705-07-9, 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 162705-07-9 as follows.

General procedure: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

According to the analysis of related databases, 162705-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
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Electric Literature of 6876-00-2, 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 6876-00-2 as follows.

EXAMPLE 29 1-(2-Fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl) cyclopropane The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.26 g), tetrahydrofuran (2 ml) and magnesium (22 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl)cyclopropane (Example 21) (0.1 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C8; solvent: methanol; flow rate: 2 ml/min) to afford 1-(2-fluoro-3-(3-phenoxyphenyl) prop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl)cyclopropane (38 mg, 27%).

According to the analysis of related databases, 6876-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; British Technology Group Limited; US5763700; (1998); A;,
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Synthetic Route of 89282-70-2, A common heterocyclic compound, 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, molecular formula is C5H13NO, 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.

[0407] In Examples, a room temperature usually indicates10 to 30 C. ?H NMR indicates a proton nuclear magnetic resonance spectrum, and chemical shift (6) is expressed in ppm, using tetramethylsilane as an internal standard substance.; [0424] The intermediate compound (1) (0.24 g, 1.0 mmol), 2-methoxy-2-methylpropylamine (0.13 g, 1.2 mmol), and HOST (0.01 g, 0.1 mmol) were added to chloroform (Amylene-added product) (2.5 mE). Afier EDCD (0.24 g, 1.2 mmol) was added to the mixed liquid at room temperature, the mixture was stirred at room temperature for 3 hours. Thereafier, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with chloroform two times. After the organic layer was passed through a short column to remove impurities, this was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.24 g of a compound offollowing formula: (hereinafier, referred to as compound (8)).; [0425] ?H-NMR (CDC13, TMS, oe(ppm)): 1.21 (6H, s),3.23 (3H, s), 3.46 (2H, d), 4.61 (2H, s), 4.65 (2H, s), 6.73(1H, s), 7.10 (1H, br s), 7.30-7.40 (5H, m)

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; SUMITOMO CHEMICAL COMPANY, LIMITED; MITSUDERA, Hiromasa; OKAJIMA, Mayumi; KOWATA, Ayano; AWASAGUCHI, Kenichiro; UJIHARA, Kazuya; (108 pag.)US2017/295789; (2017); A1;,
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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. 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Formula: C8H10FNO

General procedure: A microvawe vial (ovendried and under argon) was chargedwith the corresponding bromoindazole derivative (1.0 equiv.), theappropriate amine (1.2 equiv.), Pd(OAc)2 (5 mol%), BrettPhos(10 mol%), Cs2CO3 (1.5 equiv.) and anhydrous dioxane (0.2 mmol/mL). The vial was capped properly, flushed with argon and heatedto 120 C overnight. After cooling, the reaction mixture wasconcentrated under vacuum. The crude residue was diluted withwater and the aqueous phase was extracted 3 times with EtOAc.The organic layers were combined, washed with brine, dried overNa2SO4, filtered, concentrated and purified by silica gel columnchromatography, using the appropriate heptanes:EtOAc mixture.

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:
Article; Bollenbach, Maud; Lugnier, Claire; Kremer, Melanie; Salvat, Eric; Megat, Salim; Bihel, Frederic; Bourguignon, Jean-Jacques; Barrot, Michel; Schmitt, Martine; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 269 – 290;,
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Adding a certain compound to certain chemical reactions, such as: 34967-24-3, name is 3,5-Dimethoxybenzyl amine, 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 34967-24-3, Recommanded Product: 34967-24-3

To a stirred solution of 2,4 dichloro-pyrido [2,3-d] pyrimidine (1.3 g, 6.7 mmol) and 3, 5-dimethoxybenzylamine (1.1 g, 6.7 mmol) in 30 mL EtOH at RT was added TEA (4 mL, 28.7 mmol). A precipitate formed that was filtered off and washed with cold EtOH followed by hexanes to give 1.8 g of the title compound (82%) as a solid. mp 185C (dec).’H-NMR (DMSO-d6) 8 : 9.5 (t, 1H), 8. 9 (dd, 1H), 8.7 (dd, 1H), 7.5 (m, 1H), 6.5 (d, 2H), 6.4 (t, 1H), 4.6 (d, 2H), 3.7 (s, 6H). MS (m/z, %): 331 (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; PFIZER PRODUCTS INC.; WO2005/61497; (2005); A1;,
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