Tag: M.W=100-200

Reference of 23786-14-3, These common heterocyclic compound, 23786-14-3, name is Methyl 4-methoxyphenylacetate, 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 a solution of methyl 2-(4-methoxyphenyl)acetate (10.0 g, 55.49 mmol) in THF (100 mL) at -78 C was added methyl iodide (23.64 g, 166.5 mmol) very slowly. KO?-Bu (18.68 g, 166.5 mmol) was then added portionwise over 30 min and the reaction mixture was stirred at -78 C for 1 h followed by rt for another 1 h. The reaction was quenched by the addition of water (25 mL) and extracted with EtOAc (2 x 250 mL). The organic layer was dried over Na2S04 and concentrated to obtain the title compound (10.46 g, 91%).

The synthetic route of 23786-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; BOHNERT, Gary, J.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; SUNG, Leonard; WO2013/19682; (2013); 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. 5335-05-7, name is Chloromethyl benzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7ClO2

Chloromethyl benzoate (2.87 g, 16.82 mmol) was dissolved in acetonitrile (20 mL) and treated portionwise with sodium iodide (5.04 g, 33.6 mmol). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (x 2). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-20 % ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a yellow oil (3.15 g);1 H NMR (400 MHz, CDCI3): delta 8.06-8.03 (2H, m), 7.63-7.59 (1 H, m), 7.49-7.44 (2H, m), 6.16 (2H, s).

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; PROXIMAGEN LIMITED; DINNELL, Kevin; LIGHTFOOT, Andrew; MORTON, Gillian Elizabeth; WO2011/45353; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3377-20-6, name is Diethyl 2-methylenemalonate, belongs to esters-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 3377-20-6, COA of Formula: C8H12O4

nBuLi solution (2.5 M in hexanes, 2.4 mL, 6.0 mmol) was added, dropwise over 4 min., to a cooled (-20 C bath maintained by an immersion cooler) solution of N,N,N?-trimethylethylenediamine (655 mg, 6.41 mmol) in 2-MeTHF (14 mL). After stirring for 15 min., 4-tert-butoxybenzaldehyde (1.02 g, 5.72 mmol) was added via syringe by mass difference dropwise over 5 min. After 15 min., more nBuLi solution (2.5 M in hexanes, 6.9 mL, 17 mmol) was added, dropwise over 4 min. After stirring at this temperature for 24 h, the reaction mixture was cooled in a dry ice/acetone bath. After stirring for 20 min., diethyl ketomalonate (3.6 mL, 23 mmol) was added to the reaction mixture, dropwise over 8 min. After 5 min., the reaction was quenched by rapid addition of aq. HCl (2.0 M, 12.5 mL), and cooling was ended. The resulting mixture was partitioned between dichloromethane and half-saturated brine. The aqueous layer was extracted once more with dichloromethane, and the combined organic layers were dried (sodium sulfate) and concentrated to a clear, yellow oil (5.45 g). Chromatographic purification (354 g silica gel, heptane to 3:7 EtOAc/heptane gradient) afforded the title compound as a white solid (1.06 g, 53 % yield, ca. 90 % purity). LCMS (ESI) m/z: 375.3[M+Na] (19 %). 1H NMR (400 MHz, CDCl3) delta 1.29 (t, J = 7.1 Hz, 3H), 1.33 (t, J = 7.1 Hz, 3H), 1.35 (s, 9H), 2.48 (d, J = 7.8 Hz, 1H), 4.24 (dq, J = 10.8, 7.1 Hz, 1H), 4.32 (dq, J = 10.8, 7.1 Hz, 1H), 4.34 (dq, J = 10.7, 7.1 Hz, 1H), 4.38 (dq, J = 10.8, 7.1 Hz, 1H), 5.85 (dt, J = 7.8, 0.6 Hz, 1H), 6.64 (dd, J = 8.1, 2.0 Hz, 1H), 6.66 (dt, J = 2.0, 0.5 Hz, 1H), 7.27 (dt, J = 8.2, 0.6 Hz, 1H). 13C NMR (101 MHz, CDCl3) delta 13.9 (1C), 14.1 (1C), 28.8 (3C), 62.7 (1C), 62.7 (1C), 76.1 (1C), 79.3 (1C), 93.6 (1C), 106.4 (1C), 118.2 (1C), 120.2 (1C), 125.3 (1C), 158.6 (1C), 159.3 (1C), 165.3 (1C), 166.4 (1C).

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; Rocke, Benjamin N.; Conn, Edward L.; Eisenbeis, Shane A.; Ruggeri, Roger B.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5467 – 5470;,
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Adding a certain compound to certain chemical reactions, such as: 82782-85-2, name is Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, belongs to esters-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 82782-85-2, name: Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

Compounds e4. Dried K2CO3 (0.15 mol), alkylating agent (0.1 mol) and crown-16 (0.5 mmol) were added to the solution of compound e3 (0.1 mol) in DMF (100 ml). The suspension obtained was stirred at 80-90 C. for 4 hours, cooled to room temperature and poured into 10-fold volume of water. The precipitated solid was filtered off, washed with water, dried in the opened air and recrystallized from ethanol. The oily products were extracted three times with methylene chloride, combined extracts were washed with water, dried over MgSO4 and evaporated at reduced pressure. The residue was recrystallized from ethanol. If required, recrystallization was repeated from the proper solvent. The yield of compounds e4 was 30-75%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ALLA CHEM, LLC; US2011/53915; (2011); A1;,
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Some common heterocyclic compound, 2005-10-9, name is 6H-Benzo[c]chromen-6-one, molecular formula is C13H8O2, 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 6H-Benzo[c]chromen-6-one

4′-Bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine 8 (1.60 g,4.00 mmol) was dissolved in 25 mL of anhydrous THF in an oven dried round bottom flask. The solution was cooled to 78 C in a dry ice/acetone bath and sparged with Ar for 20 min. 2.5 M n-BuLi in hexane (1.60 mL, 4.00 mmol) was added dropwise via syringe and the reaction was stirred for 15 min at 78 C. The cooling bath was removed, and the reaction stirred for 10 min. The reaction was cooled back to 78 C and stirred another 15 min. During this time 6H-benzo[c]chromen-6-one 9 (713 mg, 3.63 mmol) was dissolved in 10 mL of anhydrous THF in a separate oven dried round bottom flask. The solution was cooled to 78 C in a dry ice/acetone bath and sparged with Ar for 10 min. The aryllithium solution was transferred to the solution containing 9 at 78 C via cannula under Ar pressure. The cooling bath was removed, and the reaction stirred for 10 min. The reaction was cooled back to 78 C and stirred another 15 min. The reaction was quenched by the addition of 20 mL of sat. NH4Cl over 10 min at 78 C. The cooling bath was removed, and the reaction was allowed to warm to rt with stirring. 20 mL of water was added, and the mixture was subsequently extracted 3x with 50 mL of EtOAc. The combined organics were washed with brine, dried with Na2SO4, filtered, and concentrated under reduced pressure to yield a crude oily solid. The crude product was purified with column chromatography under gradient elution (10:90 CH2Cl2:hexane/80:20 CH2Cl2:hexane) to yield 17a as a light-yellow powder (750 mg, 40%) but not characterized further. 300 mg (0.580 mmol) of 17a was dissolved in 20 mL of CH2Cl2 in a graduated cylinder and 0.1 mL of a neat 1:1 HBF4 diethyl ether complex and 0.5 mL of Ac2O was carefully added resulting in a blue solution. Diethyl ether (30 mL) was layered on top of the solution and was allowed to sit for 48 h as a ppt formed. The ppt was filtered to achieve a greenish/black solid (273 mg, 80%). The product was acid sensitive and was therefore analyzed via NMR spectroscopy dissolved in CD2Cl2 as a solvent with no added CF3CO2D, which reduced its solubility. mp 226e229 C. 1H NMR (400 MHz,CD2Cl2): d 8.92 (d, J 8.6 Hz, 1H), 8.84 (d, J 8.3 Hz, 1H), 8.78 (d,J 8.1 Hz, 1H), 8.60 (t, J 7.7 Hz, 1H), 8.36 (d, J 8.6 Hz, 2H), 8.27 (d,J 8.3 Hz, 1H), 8.17 (t, J 7.8 Hz, 1H), 8.15-8.02 (m, 4H), 7.73 (br,2H), 7.36 (br, 5H) 7.20 (br, 7H). 13C NMR (100 MHz, CD2Cl2): d 183.4,151.9, 144.1, 139.8, 136.5, 135.2,135.1, 132.6, 131.2, 130.2, 129.1, 128.2,127.5, 126.3, 124.7, 124.6, 124.1, 122.1, 121.0, 120.3. IR (ATR) nmax:1583, 1485, 1050 cm1. HRMS (ESI) m/z calcd for C37H26NO [M]500.2014, found 500.2023.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2005-10-9, its application will become more common.

Reference:
Article; Meyer, Samantha M.; Charlesworth-Seiler, Eva M.; Patrow, Joel G.; Kitzrow, Jonathan P.; Gerlach, Deidra L.; Reinheimer, Eric W.; Dahl, Bart J.; Tetrahedron; vol. 76; 23; (2020);,
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4341-76-8, name is Ethyl 2-butynoate, belongs to esters-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. Product Details of 4341-76-8

General procedure: In a 1 dram vial, methyl non-2-ynoate (88 mg, 1.0 equiv), 4-picoline (2.55 muL, 0.05equiv.), half the amount of bis(pinacolato)diboron (198 mg total, 1.5 equiv), and 1 mL of 1.3mg/mL CuSO4 stock solution (0.01 equiv.) are mixed and stirred vigorously at 50 C. The remaining half of bis(pinacolato)diboron is added over a period of 10 minutes. After 3 hours, 1mL of hexanes is added to quench the reaction. The aqueous layer is extracted 3x with hexanes. The hexanes layer is washed 5x with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Column chromatography is used to purify the product.

The synthetic route of 4341-76-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Peck, Cheryl L.; Calderone, Joseph A.; Santos, Webster L.; Synthesis; vol. 47; 15; (2015); p. 2242 – 2248;,
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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 17205-02-6 as follows. Product Details of 17205-02-6

To a diethyl ether solution (30 mL) containing methyl magnesium bromide (7.63 mL of a 3.0 M diethyl ether solution) was added a diethyl ether solution (5 mL) containing ethyl 3- hydroxycyclobutane carboxylate (2.05 g, 6.94 mmol), dropwise. After 2 h the reaction was carefully quenched with 3 M aqueous HCI. MgS04 was added until the evolution of gas stopped. The solution was filtered, and the solvent removed in vacuo yielding a viscous oil which was purified by silica gel chromatography (50%-100% EtOAc in hexanes) to give the title compound (419 mg, 46%). 1H NMR (CDCb) delta 1 .13 (s, 6 H), 1 .74-1 .86 (m, 4 H), 2.23-2.39 (m, 2 H), 2.66 (br s, 1 H), 4.03-4.09 (m, 1 H).

According to the analysis of related databases, 17205-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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35179-98-7, name is Chloromethyl ethyl carbonate, belongs to esters-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. category: esters-buliding-blocks

(2S,3S)-3-((2-bromo-5-fluoro-6-(2-thienyl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2- Formic acid (2.00 g, 4.69 mmol) was dissolved in DMF (20 mL)Add potassium carbonate (2.02 g, 14.20 mmol)And chloromethylethyl carbonate (0.79g, 5.70mmol),The resulting mixture was stirred at room temperature overnight.Add water (50 mL) to the reaction solution.Extracted with ethyl acetate (50 mL×3).The combined organic phases were washed with saturated brine (100 mL×3).Dry over anhydrous sodium sulfate, filter,The filtrate was concentrated under reduced pressure.The residue obtained was subjected to silica gel column chromatography(Petroleum ether / ethyl acetate (nu / nu) = 5 / 1) purification,The title compound is a pale yellow solid(1.70 g, 69%).

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Wang Yejun; Yi Kai; Lei Yibo; Zhang Yingjun; S ·geerdeman; Yan Huan; Nie Biao; Xu Juan; Chen Jianping; Chen Yunfu; Zhang Weihong; Cheng Lijun; Ye Weiliang; (197 pag.)CN110117285; (2019); A;,
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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 2033-24-1 as follows. Formula: C6H8O4

A solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (10.0g, 69.4mmol) disolved in trimethoxymethane (40mL, 366mmol) was refluxed at 110C for 3 hours.Then the reaction mixture was cooled to room temperatue and yellow crystalformed, the crystal was filtered out, washed with petroleum ether and dried in the air to give the titled compound as a light yellow crystaline solid (7.5g,59%). 1H NMR (400 MHz, Chloroform-d) delta 8.15 (s, 1H), 4.27 (s, 3H), 1.72(s, 6H).

According to the analysis of related databases, 2033-24-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cheng, Yu; Shen, Jian; Peng, Run-Ze; Wang, Gui-Feng; Zuo, Jian-Ping; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 12; (2016); p. 2900 – 2906;,
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Application of 90030-48-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 90030-48-1 name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of 1-(5-(4-chloro-2-fluorophenyl)-2-methyl-7,8-dihydro-[1 ,3,4]thiadiazolo- [2 3^2,3]imidazo[4,5-c]pyridin-6(5H)-yl)-2-((2-chloro-6-iodopyridin-3-yl)oxy)ethanone (150 mg), Cul (135 mg) and sodium 3-methoxy-3-oxopropane-1-sulfinate (124 mg) in DMSO (1.5 mL) was stirred at 130C for 2.5h. Sat. aq. NH4CI (5 mL) was added at rt and the mixture was stirred for 1 h. The mixture was diluted with EA and sat. aq. NaHC03. The layers were separated and the aq. phase was washed twice with EA. The combined org. layers were washed with aq. sat. NaCI, dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by FC (solvent: DCM/MeOH, 95/5) to afford 107 mg of a beige solid. LC- MS (A): tR = 0.88 min; [M+H]+: 642.49.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 3-methoxy-3-oxopropane-1-sulfinate, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GRISOSTOMI, Corinna; NAYLER, Oliver; REMEN, Lubos; VERCAUTEREN, Magali; WELFORD, Richard; WO2015/75023; (2015); A1;,
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