Tag: M.W=100-200

Related Products of 5941-55-9, A common heterocyclic compound, 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, molecular formula is C7H12O3, 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 cooled (-10 C) solution of (E)-ethyl 3-ethoxyacrylate (1 g, 6.94 mmol) in water (4 mL) and dioxane (4 mL) was added N-bromosuccinamide (NBS, 1.36 g, 7.63 mmol). The reaction was warmed to room temperature and stirred for one hour, at which point 6-chloropyridazin-3-amine (0.899 g, 6.94 mmol) was added reaction mixture was heated 80C for one hour. The reaction was cooled to room temperature and quenched via the addition of water. The product was extracted with ethyl acetate and the combined organic layers were washed with saturated (aq.) sodium chloride, dried over sodium sulfate, filtered, concentrated and purified using automated chromatography to provide ethyl 6-chloroimidazo[l,2-b]pyridazine-3-carboxylate (1 g, 61 % yield). LC retention time 1.42 min [O]. MS (E+) m/z: 226 (MH+).

The synthetic route of 5941-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
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Electric Literature of 61367-07-5, 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. 61367-07-5 name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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 mixture of 2,4,6-trichloropyridine (2.22 g, 12.20 mmol), methyl trans-4-aminocyclohexanecarboxylate hydrochloride (2.6 g, 13.42 mmol) and cesium carbonate (6.74 g, 48.8 mmol) in DMF (30 mL) was stirred in a sealed tube at 150 C. After 5.5 hours, the crude was poured on water (30 mL) and EtOAc (30 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated. Purification of the residue by flash chromatography (hexanes/ethyl acetate 15% to 30% ethyl acetate) gave the title compound (1.02 g, 28%) as a yellow solid.LRMS (m/z): 303/305 (M+1)+.1 H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.24 (m, 4H), 1.6 (m, 2H), 2.11 (m, 2H), 2.31 (m, 1 H), 3.26 (m, 1 H), 3.69 (s, 3H), 4.32 (d, J = 7.3 Hz, 1 H), 6.34 (s, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Forns Berenguel, Maria Pilar; Castillo Mcquade, Marcos; Erra Sola, Montserrat; Mir Cepeda, Marta; EP2441755; (2012); A1;,
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Electric Literature of 27492-84-8,Some common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, molecular formula is C9H11NO3, 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.

[0542] To a solution of 269-2 (14.4 g, 8 mmol) in EtOH (120 mL) was added acetic anhydride (9.0 g, 88 mmol). The mixture was allowed to stir at 50 °C for 2 h. The mixture was cooled to r.t., and neutralized with aqueous NaHC03 solution. The mixture was extracted with EA (3 x 60 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated at low pressure. The residue was purified by flash column chromatography on silica gel (PE:EA 1 : 1 ) to give 269-3 (15.0 g. 84.1 percent). +ESI-MS:m/z 223.9 [M+H]+.

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

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); 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. 454-31-9, name is Ethyl 2,2-difluoroacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 454-31-9

Step 2 Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione Ethyl difluoroacetate (4.06 g, 32.7 mmol) was placed in a 250 mL Erlenmeyer flask, and dissolved in methyl tert-butyl ether (50 mL). To the stirred solution was added 25% sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone from Step 1 (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected, washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.; 1 H NMR (DMSO-d6) 8.0 (m, 3H), 7.3 (t, 1H), 6.9 (s, 1H), 6.5 (t, 1H), 3.9 (s, 3H).

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US5756529; (1998); A;,
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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. 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 3-(4-fluorophenyl)propiolate

To a solution of N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (9.0 g, 30.0 mmol) in DCM (100 mL) was added (O-(mesitylsulfonyl)hydroxylamine) (20 g, 92 mmol) in DCM (20 mL) dropwise quickly at 0C under N2, and stirred for 2 h at room temperature. After concentrated and the residue was dissolved in MeOH, and re-concentrated again. The residue was dissolved in DMF (20 mL), and then added slowly dropwise to a mixture of methyl 3-(4-fluorophenyl)propiolate (6 g, 34 mmol) and K2C03 (21 g, 154 mmol) in DMF (100 mL) at 0C under N2. The mixture was stirred overnight at room temperature. The reaction mixture was then concentrated in vacuo and the resulting residue was suspended in H20 and extracted with DCM. The organic layer was washed with H20, brine and concentrated in vacuo. The residue obtained was purified using flash column chromatography on silica gel (eluted with PE / EtOAcfrom 5 / 1 to 3 / 1) to give methyl 5-(benzyloxy)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)pyrazolo [1 ,5-a]pyridine-3 -carboxylate (3.5 g, yield: 24%). ?H-NMR(CDC13, 400 MHz) oe 8.54 (s, 1H), 7.70-7.74 (m, 2H), 7.68 (s, 1H), 7.42-7.44 (m, 5H), 7.13 (t, J= 8.8 Hz, 2H), 5.24 (s, 2H), 3.80 (s, 3H), 3.29 (s, 3H), 2.81 (s, 3H). MS (M+H): 484.

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 42122-44-1.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); A1;,
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Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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. Formula: C9H11NO2

Step 1: A stirred solution of compound 14 (1.0 g, 6.1 mmol) in acetic acid (10 mL) was treated dropwise with a solution of bromine (1.5 mL, 12 mmol) in acetic acid (5 mL). On completion of the addition, the resultant suspension was stirred at room temperature for 30 minutes, then water (50 mL) was added. A thick white ppt formed which was filtered, washed with water (3×50 mL) and air dried. The solid still contained water, so it was dissolved in dichloromethane and the solution was dried by passing through a hydrophobic frit. Evaporation of the solvent under reduced pressure afforded compound 15 as a cream solid (1.90 g). 1H NMR (400MHz, CDC13) delta 8.02 (s, 1H), 6.23 (br. s., 2H), 3.85 (s, 3H), 2.67 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6933-47-7, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MITCHELL, Glynn; MULHOLLAND, Nicholas, Phillip; BHONOAH, Yunas; (44 pag.)WO2016/198585; (2016); A1;,
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Electric Literature of 135908-33-7, 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. 135908-33-7 name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 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.

Example 874-{[N-cyano-2-methyl-2-phenoxypropanimidoyl]amino}bicyclo[2.2.2]octane-1-carboxylic acidEthyl N-cyano-2-methyl-2-phenoxypropanimidoate (CI-1) (1 mmol) and methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate (BA-2) (1 mmol) were mixed, and the neat mixture was heated to 100 C. under nitrogen and stirred for 5 hours. After cooling, the mixture was purified by column chromatography on silica gel (mobile phase:CH2Cl2/CH3OH=50/1) to give an impure ester product which was dissolved in methanol (10 mL). To the solution was added a solution of LiOH (10 mg) in methanol (40 mL) and water (1 mL). The mixture was refluxed overnight. After removal of the solvent, the residue was dissolved in water and adjusted pH=56 with HCl (1 mol/L), extracted with ethyl acetate (50 mL×3). The combined extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative reverse phase HPLC [Waters 2767; Benetnach 10-C18 20×250 mm, 10 mum; 35-60% acetonitrile/water (0.05% trifluoroacetic acid), 30 mL/minute; detection at 214 and 254 nm] to give the titled compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT LABORATORIES; US2010/267738; (2010); A1;,
Ester – Wikipedia,
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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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, A new synthetic method of this compound is introduced below., Computed Properties of C5H7BrO2

General procedure: To a 20 mL two-necked round-bottom flask attached with areflux condenser were added V-65 (25 mg, 0.1 mmol) and K2CO3(138 mg, 1.0 mmol), and this flask was purged with argon.Then, 1-nonanal (1a, 71 mg, 0.5 mmol), methyl 2-(bromomethyl)acrylate (2a, 269 mg, 1.5 mmol), and degassedbenzene (5 mL) were added. The mixture was stirred at 60 C for1 h. The reaction mixture was filtered through a short plug ofCelite, and the filtrate was concentrated under reduced pressure.The residue was purified by flash column chromatographyon SiO2 (hexane/EtOAc = 1:0 to 30:1) and preparative HPLC(chloroform) to give methyl 2-methylene-4-oxododecanoate(3b, 101 mg, 84%).

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; Kippo, Takashi; Kimura, Yuki; Ueda, Mitsuhiro; Fukuyama, Takahide; Ryu, Ilhyong; Synlett; vol. 28; 14; (2017); p. 1733 – 1737;,
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Adding a certain compound to certain chemical reactions, such as: 454-31-9, name is Ethyl 2,2-difluoroacetate, 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 454-31-9, SDS of cas: 454-31-9

Intermediate 6 (53.35 g, 0.22 mol) was stirred in toluene (1500 mL) at 0 C under N2. Potassium tert-butoxide (34.14 g) was added at 0-5 C and 2,2-difluoro-acetic acid ethyl ester (33.01 g, 0.27 mol) was added dropwise at 0-5 C. The RIVI was stirred at RT for 2 h, then washed with 10% H2S04 in water and the OL was dried on MgSO4,filtered and evaporated, yielding intermediate 7 (70.50 g, quantitative).

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; JANSSEN PHARMACEUTICA NV; VAN ROOSBROECK, Yves, Emiel, Maria; VAN DEN KEYBUS, Frans, Alfons, Maria; VELTER, Adriana, Ingrid; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; (76 pag.)WO2018/83101; (2018); A1;,
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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 64123-77-9 as follows. name: Methyl 2-(3-fluorophenyl)acetate

Methyl 2-(3-fluorophenyl)acetate (1.90 g, 1 1.3 mmol) and N-bromo succinimide (2.01 g, 1 1.3 mmol) were dissolved in CC14 (80 ml). HBr (64 ul,0.56 mmol) was added and the mixture was stirred under reflux overnight. The mixture was cooled at room temperature, diluted with DCM and washed with sat. NaHCO3, water and brine. The organic layer was dried (Na2SO4), filtered and evaporated obtaining intermediate 115 (2.68 g, 96% yield).

According to the analysis of related databases, 64123-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; RICCABONI, Mauro; WO2011/160919; (2011); A1;,
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