Tag: M.W=100-200

Application of 54149-17-6, A common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11BrO2, 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.

1-(2-Bromo-ethoxy)-2-methoxy-ethane (107 mg, 0.58 mmol) was added to a suspension of 4- hydroxy-2-(4-methoxy-benzyl)-isoindole-1 ,3-dione (150 mg, 0.53 mmol) and potassium carbonate (200 mg, 1.4 mmol) in DMF (2 mL). After 3.5 hours, a catalytic amount of potassium iodide was added. After a further 17 hours, the mixture was warmed to 60C. After 3 hours, an additional amount of 1-(2-bromo-ethoxy)-2-methoxy-ethane (20 mg, 0.11 mmol) was added and the mixture maintained at 6O0C for a further 20 hours. The mixture was concentrated in vacuo then the residue was taken up in ethyl acetate and washed with potassium carbonate solution and brine. The organic phase was dried (MgSO4) and concentrated to give the title compound as a yellow oil (149 mg, 73%). 1H NMR (methanol-d4) 7.71 (1 H, t), 7.43-7.40 (2H, m), 7.31-7.27 (2H, m), 6.87-6.83 (2H, m), 4.71 (2H, s), 4.37-4.34 (2H, m), 3.92-3.89 (2H, m), 3.77-3.74 (5H, m), 3.55-3.53 (2H, m), 3.33 (3H, s). MS: [M+H]+ 386.

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
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Electric Literature of 592-55-2, 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 592-55-2 as follows.

Add 3 g of potassium hydroxide solid to a 250 mL flask, then add 30 mL of DMF and stir well. After the above system was stirred for 10 minutes, 2 g of compound 2 was added thereto, and then the system was stirred for 30 minutes. Subsequently, 1.38 mL of was added2-bromoethyl ether, the reaction 18 hours at room temperature. After the reaction was completed, the above system was poured into 400 mL of water and extracted with 400 mL of dichloromethane. The organic layer was dried with 4 g of anhydrous magnesium sulfate and the solvent was evaporated to give a white product in a yield of 81%.

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong University; Yu Xiaoqiang; Tian Minggang; He Xiuquan; Zhang Ruoyao; (11 pag.)CN106632264; (2017); 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Safety of 1-(3-Methoxyphenyl)-N-methylmethanamine

General procedure: To a solution of bromobenzoyl chloride (2 mmol) was added the corresponding N-methylaniline (2 mmol) followed by Et3N (2 mmol) in CH2Cl2 (10 mL) at 0 C. After a few minutes, the ice bath was removed and the reaction mixture was warmed up to room temperature and stirred at room temperature overnight. The reaction mixture was extracted twice with CH2Cl2 (2 × 15 mL). The organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexanes and EtOAc as eluent or by trituration in a mixture of diethyl ether / petroleum ether to afford the desired compound.

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; Gargano, Emanuele M.; Allegretta, Giuseppe; Perspicace, Enrico; Carotti, Angelo; Van Koppen, Chris; Frotscher, Martin; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; PLoS ONE; vol. 10; 7; (2015);,
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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.

A mixture of 2-chloropyrimidine (2.00 g, 17.50 mmol), (2,4-dimethoxyphenyl)methanamine (2.92 g, 17.50 mmol) and potassium carbonate (2.90 g, 21.00 mmol) in anhydrous acetonitrile (20 mL) was degassed with by sparging with nitrogen, and then stirred to 80 C. for 10 h. After cooling to ambient temperature, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography, eluting with 50% of petroleum ether in ethyl acetate, to afford the title compound as a yellow solid (2.10 g, 49% yield): 1H NMR (400 MHz, CDCl3) delta8.27 (d, J=4.5 Hz, 2H), 7.24 (d, J=8.3 Hz, 1H), 6.50 (t, J=4.8 Hz, 1H), 6.47 (d, J=2.5 Hz, 1H), 6.43 (dd, J=8.3, 2.5 Hz, 1H), 5.58 (br s, 1H), 4.55 (d, J=6.0 Hz, 2H), 3.83 (s, 3H), 3.80 (s, 3H).

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; Xenon Pharmaceuticals Inc.; Andrez, Jean-Christophe; Bogucki, David Earl; Burford, Kristen Nicole; Chowdhury, Sultan; Cohen, Charles Jay; Decker, Shannon Marie; Dehnhardt, Christoph Martin; Devita, Robert Joseph; Empfield, James Roy; Focken, Thilo; Grimwood, Michael Edward; Hasan, Syed Abid; Jia, Qi; Johnson, JR., James Philip; Wilson, Michael Scott; Zenova, Alla Yurevna; (287 pag.)US2018/162868; (2018); A1;,
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These common heterocyclic compound, 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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. HPLC of Formula: C4H7ClO3

In a glass RBF equipped with a Teflon-coated magnetic stirrer was dissolved (2-chloro-ethoxy)- acetic acid (1 eq.) in dichlormethane (0.67 M). To this was then added sequentially pyridine (2.5 eq.) and thionyl chloride (1.5 eq.), the latter of which was added drop-wise over 10 mm. The resulting orange solution was stirred at RT under nitrogen for 30 mm before 2-bromo-4-fluoro-5- nitro-phenylamine (1 eq.) was added drop-wise as a solution in dichloromethane (0.67 M). Finally, triethylamine (3.5 eq.) and DMAP (0.1 eq.) were added and the resulting mixture was allowed to stir at RT for 18 h. The reaction was quenched with the addition of water and extracted with EtOAc. The combined organic extracts were then washed further with water and brine, dried over MgS 04, filtered and the filtrate concentrated in vacuo. Further purification by way of column chromatography (Si02, gradient elution, 9:1 (v/v) Hex: EtOAc – EtOAc) furnish the desired product as an orange oil that solidified upon standing (51percent yield).

The synthetic route of 2-(2-Chloroethoxy)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Formula: C7H6F3NO

General procedure: To a mixture of substituted phenyl amine (0.06 mol) and 20% HCl (50 mL), NaNO2 (0.123 mol) in H2O (200 mL) was added drop-wise at 0 C. After the completion of addition, the reaction mixture was stirred at this temperature for 30 min, and then it is dropped into the mixture of appropriate intermediate (10a or 10b) (0.047 mol), sodium acetate anhydrous (10.2 g, 0.124 mol), EtOH (200 mL) at 0 C. Upon completing the addition, the mixture was filtered and the cake was dried to give light yellow to white solid (11a-t, 12a and 12b) yielded 75-80%.

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; Li, Sai; Zhao, Yanfang; Wang, Kewen; Gao, Yali; Han, Jianming; Cui, Bingbing; Gong, Ping; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 2843 – 2855;,
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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.

A reaction vessel containing a stirrer, a thermometer and a dropping funnel was charged with 1.36 mol of a 25% sodium sulfite solution, 1.7 mol of a mixture of beta-aminopropanal (2), a mass fraction of 55% Of 2-nitrophenol solution (3) 2.3mol, strontium chloride 0 · 56mol, acetonitrile 300ml, control the stirring speed at 180rpm, raise the temperature of the solution to 135 C, the reaction 9h, static stratification, remove the oil layer , Washed with sodium bromide solution, the mass fraction of 65% isopropyl alcohol, the mass fraction of 75% triethylamine washing, 1.9kPa vacuum distillation, collecting 90-95 C fractions, in the mass fraction of 90% toluene Recrystallization gave 103.43 g of crystalline diethanol acrolein in 83% yield.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu qianyu Longhua Petroleum Engineering Consulting Co. Ltd.; Guan, genan; (5 pag.)CN105503547; (2016); A;,
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Electric Literature of 7252-83-7,Some common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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 a stirred solution of 3-bromothiophenol (10.0 g, 52.88 mmol) in DMF (180 mL) was added NaH (3.0 g, 63.45 mmol) portionwise at 0C. After the addition, the reaction mixture was stirred at room temperature for 30 mi Bromoacetaldehyde dimethylacetal (6.85 mL, 58.17 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (250 mL) and washed with cold water and brine solution. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford the crude material which was purified by column chromatography using silica gel (100-200 mesh) and 2% EtOAc-hexane as eluent to afford 1-bromo-3-(2,2-dimethoxy- ethylsulphanyl)-benzene (11.0 g, 36.038 mmol, 68%) as colorless liquid. GCMS: 277 (mlz).

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

Reference:
Patent; CURADEV PHARMA PRIVATE LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Dharmendra B.; YADAV, Veejendra K.; KAPOOR, Kamal Kishore; VENKATESAN, Aranapakam; SMITH, Roger A.; THOMPSON, Scott K.; WO2014/186035; (2014); A1;,
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Electric Literature of 450-91-9, These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-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.

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (15.0 g), 4-fluoro-2-methoxyaniline (9.5 g), 4M hydrochloric acid in dioxane (4.5 ml) and dioxane (100.0 ml) were stirred at 100 C. overnight. Then the mixture was filtrated and the solid was dried in vacuo. Yield: 24.0 g ESI mass spectrum: m/z=348 (M+H)+

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/212103; (2011); A1;,
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Synthetic Route of 70894-71-2, A common heterocyclic compound, 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine, molecular formula is C11H15NO, 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.

6-Chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile To a stirred solution of 6,8-dichloroimidazo[1,2-b]pyridazine-3-carbonitrile and 8-bromo-6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile (15 g, 71.09 mmol) in THF (20 mL) was added DIPEA (14 mL, 78.19 mmol) at room temperature under argon atmosphere, prior to the addition of N-(4-methoxybenzyl)cyclopropanamine (13.99 g, 78.19 mmol) at room temperature. The reaction mixture was stirred for 4 h at 65 C. The reaction mixture was quenched with water and extracted with ethyl acetate (2*200 mL). The combined extracts were washed with brine, dried over Na2SO4, concentrated to give the crude product, which was purified on a silica gel column (eluting with 20% ethyl acetate: pet ether) to get the title compound 6-chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile (18 g, 71.1%) as a pale yellow solid. ES+, m/z 354.4 [M+1].

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; Polaris Pharmaceuticals; WEBBER, Stephen E.; TAO, Xueliang; BRIN, Elena; (85 pag.)US2017/369489; (2017); A1;,
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