Month: August 2021

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. 6290-49-9, name is Methyl 2-methoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H8O3

To a solution of 5-methoxy-2-(t fluoromethyl)-4-(t methylsilyl)py dine (5 g, 20.06 mmol) in Tetrahydrofuran (10 mL) cooled to -70 C was added dropwise -BuLi in hexane (23.14 mL, 30.1 mmol) over a period of 30 min. After the addition was complete, the mixture was stirred for 1 h. Methyl 2-methoxyacetate (3.13 g, 30.1 mmol) was then added dropwise and the resulting mixture was stirred for 1 h before being allowed to warm to rt. The reaction was quenched with aqueous NH4CI (100 mL) and the mixture was extracted with ethyl acetate (3 x 50mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc = 19/1 ) to give the title compound 2-methoxy-1 -(3-methoxy-6-(trifluoromethyl)- 4-(trimethylsilyl)pyridin-2-yl)ethanone (5 g, 15.56 mmol, 78 % yield) as a yellow oil. m/z: [M + H]+ Calcd for C13H19F3NO3S1 322.1 ; Found 322

According to the analysis of related databases, 6290-49-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
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Application of 6627-89-0, 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. 6627-89-0, name is tert-Butyl phenyl carbonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Neat tert-butyl phenyl carbonate (284 mg, 271 uL, 1.46 mmol) was added to a solution of Nu,Nu’- bis(3-aminopropyl)butane-1,4-diamine (296.0 mg, 1.46 mmol) in ethanol (2.0 ml_) and the contents heated to reflux with stirring for 18 hours. The reaction mixture was concentrated to a pale yellow-colorless oil under vacuum and purified by reverse phase HPLC (Method J). Product containing fractions were lyophilized to obtain 221 mg (23%) of the desired product. LC-MS m z 303.3 [M+H+]; retention time = 0.26 minutes (Method 5). 73 mg (8%) Of tert-butyl (2,2-dimethyl-4-oxo-3-oxa-5,9,14-triazaheptadecan-17-yl)carbamate was also obtained; LC-MS m/z 403.4 [M+H+]; retention time = 0.47 minutes (Method 5).

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, tert-Butyl phenyl carbonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; AHMAD, Omar Khaled; BROWN, Stephen Paul; DIRICO, Kenneth John; DUSHIN, Russell; FILZEN, Gary Frederick; PUTHENVEETIL, Sujiet; STROP, Pavel; SUBRAMANYAM, Chakrapani; TUMEY, Lawrence N.; (402 pag.)WO2018/138591; (2018); 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. 711-01-3, name is Methyl adamantane-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H18O2

To 40 g (206 mmol) of methyl 1-adamantanecarboxylate obtained in Production Example 1, 40 g of toluene was added and the atmosphere was replaced with nitrogen, and cooled with refrigerant. While keeping the toluene solution at 10 ° C. or less, 247 g (494 mmol) of methyl magnesium chloride in THF solution (2 M) was added dropwise over 4.5 hours. After that, the temperature was raised naturally and the reaction was carried out at room temperature (25 ° C.) for 3 hours. The reaction solution was again cooled with a coolant, while keeping the temperature below 10°C, 82.3 g (534 mmol) of methacrylic anhydride was added dropwise over 3.3 hours. Thereafter, the temperature was allowed to rise naturally, and the reaction was allowed to proceed at room temperature (25 ° C.) for 3 hours. The measurement results of this crude reaction solution by GC were as follows. Residual material = methyl 1-adamantanecarboxylate: 1.5percent, By-product = 1-(1-adamantyl) -1-methylethanol: 7.3percent and target product=1- (1-adamantyl) -1-methylethyl methacrylate: 91.2percent. While maintaining the crude reaction solution at 25 ° C. or less, magnesium salt was decomposed with hydrochloric acid aqueous solution, the aqueous layer was separated. After washing with 10percent aqueous sodium hydroxide solution and saturated brine, and concentrated. By concentrating the concentrated solution from methanol, 1-(1-adamantyl)-1-methylethyl methacrylate (37 g) was obtained. The isolation yield was 68.5percent. The purity measured by GC was 98.3percent by mass.

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Osaka Organic Chemical Industry Co., Ltd.; Tanaka, Shinji; Uenoyama, Yoshitaka; Kono, Naoya; Ono, Hidetoshi; Kojima, Akio; (11 pag.)JP5993171; (2016); B2;,
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Application of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, 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.

2,2-Diphenylacetohydrazide To a stirred solution of methyl 2,2-diphenylacetate (0.5 g, 1 equiv) in anhydrous EtOH (150 mL) was added hydrazine hydrate (8 mL) and heated to reflux. Stirring was then continued for 1 hour. The reaction mixture was then cooled and the solvents removed under reduced pressure. The crude oil was diluted with EtOAc and washed with H2O and the organic phase dried over Na2SO4, filtered, and the solvents removed under reduced pressure to yield a yellow oil (0.97 g, 97%) that was used without further purification.

The synthetic route of 3469-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Omeros Corporation; US2010/35872; (2010); A1;,
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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. 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H9ClO3

Example-113 Potassium carbonate (95 mg, 0.69 mmol) and methyl (E)-4-chloro-3-methoxy-2-butenoate (114 mg, 0.69 mmol) were added to a solution of 5-chloro-4-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,2-tetramethylene-4-pyrazolin-3-one (200 mg, 0.63 mmol) in DMF (2 mL), followed by stirring at 50 C. for 5 hours. After the reaction was completed, water (20 mL) was added to the reaction solution, and the resultant product was extracted with ethyl acetate (20 mL*2, 10 mL*1). The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and was concentrated under reduced pressure, whereby a pale yellow oily crude product (319 mg) was obtained. This was purified by silica gel column chromatography (ethyl acetate), whereby methyl (E)-4-[2-chloro-5-(5-chloro-3-oxo-1,2-tetramethylene-4-pyrazolin-4-yl)-4-fluorophenyloxy]-3-methoxy-2-butenoate (283 mg, yield: quantitative) was obtained as a pale yellow oily material. 1H-NMR (400 MHz, CDCl3): delta1.87-1.92 (m, 2H), 1.99-2.03 (m, 2H), 3.60-3.62 (m, 2H), 3.69 (s, 3H), 3.72 (s, 3H), 3.80-3.83 (m, 2H), 5.21 (s, 1H), 5.27 (s, 2H), 7.13 (d, J=6.3 Hz, 1H), 7.17 (d, J=9.1 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-119 (s, 1F).

According to the analysis of related databases, 110104-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
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Application of 146307-51-9,Some common heterocyclic compound, 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, molecular formula is C13H23NO4, 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 2 trans-Methyl 4-((tert-butoxycarbonyl)(methyl)amino)cyclohexanecarboxylate To a solution of trans-methyl 4-((tert-butoxycarbonyl)amino)cyclo hexanecarboxylate (1.7 g, 6.6 mmol) in DMF (50 mL) was added NaH (1.05 g, 26.4 mmol, 60% in mineral) at room temperature. The reaction mixture was stirred at room temperature for 1 h. Iodomethane (9.9 g, 69.7 mmol) was added into the reaction mixture and the reaction mixture was stirred at room temperature for 18 h. TLC (PE / EtOAc = 4 : 1) showed the starting material has been consumed. The mixture was neutralized with HCl (2N) till pH ~7. The reaction mixture was added into 100 mL of water. The aqueous was extracted with EtOAc (70 mL x 2). The combined organic layers were dried over anhydrous (1204) Na2S04 and concentrated in vacuum to give trans-methyl 4-((tert- butoxycarbonyl)(methyl)amino)cyclo hexanecarboxylate (1.3 g, yield 72%) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; KUMARAVEL, Gnanasambandam; PENG, Hairuo; XIN, Zhili; WO2015/188051; (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. 618-89-3, name is Methyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 618-89-3

Methyl 3-bromobenzoate (110 g, 0.51 mol), dry acetonitrile (500 mL), ethynyl(trimethyl)silane (60.0 g, 0.61 mol), diisopropylamine (62.0 g, 0.61 mol) and tetra(triphenylphosphine)palladium (23.6 g, 0.02 mol) were placed under an atmosphere of argon in a three-necked round-bottomed 1 liter flask, equipped with a magnetic stirrer and a thermometer. The mixture was stirred for 30 minutes and then cooled to 10 0C. Copper iodide (9.7 g, 0.06 mol) was added, and the obtained suspension was stirred for a further 2.5 hours at 20 0C and finally for 3 hours at 60 0C. Then the mixture was left to stand at room temperature overnight and filtered. The precipitate of hydrobromide was washed with ether, and the combined filtrate was washed with saturated aqueous solutions of NH4CI and NaCI, dried over Na2SO4 and evaporated. The crude product was purified by chromatography (hexane) on a silica gel column to give methyl 3-(2- (trimethylsilyl)ethynyl)benzoate in 95% (112.8 g) yield.A suspension of methyl 3-(2-(trimethylsilyl)ethynyl)benzoate (112.8 g, 0.48 mol), mercury(2+) diacetate (16.2 g, 0.005 mol) in THF (350 mL) and concentrated H2SO4 (40 mL) was stirred at 60 0C for 3 hours. Then the mixture was cooled, diluted with ether (500 mL), filtered to remove precipitated mercury salts and washed to obtained neutral medium. Then the solution was dried over Na2SO4 and evaporated. The residue was purified by chromatography (hexane/ethyl acetate 4:1) on a silica gel column to give methyl 3-acetylbenzoate in 75% (65.2 g) yield.(Dimethoxymethyl)dimethylamine (90 mL) was added to a suspension of methyl 3-acetylbenzoate (65.2 g, 0.27 mol) in toluene (90 mL). The mixture was refluxed for 9 hours, during which time forming methanol was distilled off. The solution was then concentrated in vacuo, and the residue was purified from ether by crystallization to give methyl 3-(3-(dimethylamino)acryloyl)benzoate as yellow prismatic crystals in 80% (68.1 g) yield. ‘ . lmidoformamide acetate (20.3 g, 0.19 mol) was added to a suspension of methyl 3-(3- (dimethylamino)acryloyl)benzoate (30.3 g, 0.13 mol) in toluene (300 mL). The reaction mixture was refluxed for 20 hours, during which time toluene and dimethylamine acetate were distilled off* Then imidoformamide acetate (6.7 g) and toluene (175 mL) were added again, and after 8 hours the mixture was evaporated in vacuo. The residue was purified by chromatography (ethylacetate/hexane 3:1) on a silica gel column to afford methyl 3-(pyrimidin-4-yl)benzoate in 70% (19.5 g) yield.A suspension of methyl 3-(pyrimidin-4-yl)benzoate (19.5 g, 0.091 mol), sodium methylate (7.6 g, 0.14 mol) in ethanol (250 mL) was refluxed for 30 minutes. Then the reaction mixture was cooled, and the formed-precipitate was separated by filtration was dissolved in water. The obtained solution was acidified with concentrated HCI to pH about 2 that caused precipitation. The precipitate was separated by filtration, washed with water and dried to give the title compound as crystals in 94% (17.2 g) yield.

The synthetic route of 618-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65508; (2008); A1;,
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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. 3153-37-5, name is Methyl 4-chlorobutyrate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H9ClO2

In a 1000 ml reactor, 1 mol of calcium carbide was added, and after sealing, the air was replaced with nitrogen 3 times.4 mol of methanol was initially added dropwise and acetylene gas was collected until the end of the reaction. Then, 1.8 mol of methyl gamma-chlorobutyrate was added dropwise to the reactor to control the dropping rate and keep the temperature constant at 100 C., while collecting the methanol fraction produced during the dropping process. After the reaction was completed, the temperature was distilled by distillation. Fractions were collected to obtain 170.3 g of methyl cyclopropanecarboxylate in a yield of 94.5%.

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 3153-37-5.

Reference:
Patent; Shandong Guobang Pharmaceutical Co., Ltd.; Lu Huawen; Li Qibin; Wang Weihong; Liao Shixue; Li Jinwei; Liu Cong; (5 pag.)CN107673973; (2018); A;,
Ester – Wikipedia,
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Synthetic Route of 454-31-9, 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.

EXAMPLE 8 Ethyl 3,5-bis(difluoromethyl)-1H-pyrazole-4-carboxylate (Ia/b-3) To a mixture of (3.44 g, 10 mmol) ethyl 3-[(diphenylmethylene)hydrazinylidene]-4,4-difluorobutanoate and 1.02 g of ethyl difluoroacetate in 15 ml of methyl tert-butyl ether are added 1 g of potassium tert-butoxide and the mixture is stirred for 18 hours at 40 C. The mixture is cooled to 20 C., the precipitate is filtered off and dissolved in 15 ml of ethanol 2 ml of HCl were added to the solution and the mixture is stirred for 3 hours at 50 C. The product is extracted with 50 ml of methyl tert-butyl ether. The organic phase is washed with water, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by means of column chromatography (ethyl acetate/methylcyclohexane). 1.87 g (78%) of product is obtained. 1NMR delta: 7.15 (t, 2h, CHF2, JH-F=53.6 Hz), 4.39 (q, 2H, CH2, J=7.1 Hz), 1.39 (t, 3H, CH3, J=7.1 Hz) ppm. 13C NMR delta: 161.1 (CO), 143.8 (t, CIV arom, JC-F=23.1 Hz), 111.6 (CIV arom), 108.2 (t, JC-F=238.4 Hz), 61.7 (CH2), 13.9 (CH3) ppm. 19F NMR delta: -117.3 (CHF2, JF-H=53.6 Hz) ppm.

The synthetic route of Ethyl 2,2-difluoroacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; PAZENOK, Sergii; LUI, Norbert; (10 pag.)US2016/122304; (2016); 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, A new synthetic method of this compound is introduced below., Application In Synthesis of Diethyl 2-bromo-2-methylmalonate

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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