Month: August 2021

Related Products of 1186-73-8, These common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, 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.

Step 1: Methyl 10-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-2,5,6,7-tetrahydro-lH-benzo[6,7]cyclohepta[l,2-b]pyridine-3-carboxylate The crude imine was combined with diphenyl ether (5 mL) and trimethylmethanetricarboxylate (1.07 g, 5.63 mmol). The reaction was stirred in a pre-heated 190 C bath for 1 hr. After cooling to room temperature, the mixture was purified by silica gel chromatography (5-50% EtOAc in hexanes). Trituration with acetone yielded the title compound (620 mg, 49%) as an off-white solid. 1H NMR (acetone- d6): delta 1.45 (m, 1H), 1.85-2.05 (m, 2H), 2.26 (m, 1H), 2.53 (dd, J = 13 Hz, 6 Hz, 1H), 2.96 (dd, J = 14 Hz, 6 Hz, 1H), 3.61 (s, 3H), 3.75 (s, 3H), 3.94 (s, 3H), 5.05 (d, J = 16 Hz, 1H), 5.28 (d, J = 16 Hz, 1H), 6.41 (m, 2H), 6.81 (d, J = 8.5 Hz, 1H), 7.27 (d, J = 8.5 Hz, 1H), 7.37 (m, 1H), 7.41 (dd, J = 8 Hz, 2.5 Hz, 1H), 13.83 (s, 1H)

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
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Synthetic Route of 2435-36-1, 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. 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution a solution of LDA (33.6 mL, 67.1 mmol) in 10 mL THF was added a solution of dimethyl cyclopentane-1, 3-dicarboxylate (5 g, 26.9 mmol) in 10 mL THF under N2 protection dropwise at -78 and stirred at -78 for 25 mimutes. To the solution was added iodomethane (9.53 g, 67.1 mmol) dropwise and stirred at ROOM TEMPERATURE for another 16 houtrs. The solution was poured into water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4, concentrated in vacuo to give the title compound. 1H NMR (400MHz, CDCl3) : delta3.66 (major) , 3.63 (minor) (s, 6H) , 2.29-2.20 (m, 2H) , 2.12 (s, 2H) , 1.65-1.55 (m, 2H) , 1.30 -1.20 (m, 6H) ppm.

The synthetic route of Dimethyl cyclopentane-1,3-dicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ANDRESEN, Brain M.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (111 pag.)WO2016/106624; (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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2,2-dimethoxyacetate

Lithium hydroxide monohydrate (89.5 mmol, 3.75 g,1.2 equiv) was added at 0 C to a solution of methyl dimethoxyacetate (74.6 mmol, 10 g, 1 equiv) in dioxane (45 mL) and water (45 mL). The mixture was stirred for 1 h at 0 C and one additional hour at room temperature. Sodium hydroxide (1M aq soln, 75 mL) was subsequently added and the mixture extracted with diethyl ether (3 x 75 mL). The recovered aqueous layer was acidified with hydrogen chloride (6N aq soln) until a pH of 1-2 then the organics extracted with diethyl ether (3 x 75 mL). The combined organic layers were subsequently dried with magnesium sulfate, filtrated and the solvent slowly evaporated under reduced pressure to conduct to the desired carboxylic acid in a quantitative yield. Colorless liquid; Yield: 99%

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; Munyemana, Francois; George, Isabelle; Devos, Alain; Colens, Alain; Badarau, Eduard; Frisque-Hesbain, Anne-Marie; Loudet, Aurore; Differding, Edmond; Damien, Jean-Marie; Remion, Jeanine; Van Uytbergen, Jacqueline; Ghosez, Leon; Tetrahedron; vol. 72; 3; (2016); p. 420 – 430;,
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6274-50-6, name is Methyl 2-(4-methoxyphenyl)-2-methylpropanoate, 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 6274-50-6

To a solution of methyl 2-(4-methoxyphenyl)acetate (10.0 g, 48.00 mmol) in MeOH (20 mL) was added dropwise a solution of NaOH (7.69 g, 192.3 mmol) in water (50 mL). The reaction mixture was stirred at rt for 6 h. The MeOH was distilled off at reduced pressure and water (25 mL) was added. The aqueous layer was washed with Et20 and then acidified to pH=4 using 6.0 M HC1. The resultant precipitate was filtered, washed with hexanes, and dried. The resultant solid was dissolved in CH2CI2 (150 mL) and cooled to -78 C followed by the addition of BBr3 (1.0 M solution in CH2C12) (72.0 mL, 72.00 mmol) over 30 min. After the completion of the addition, the temperature was raised to 0 C, and the reaction mixture was stirred for an additional 30 min. Water was slowly added and the organic layer was separated, dried over Na2S04; and concentrated to provide the title compound (4.30 g, 50%). lU NMR (400 MHz, DMSO-d6) delta ppm 12.17 (br s, 1H), 9.31 (s, 1H), 7.14 (d, 2H), 6.71 (d, 2H), 1.42 (s, 6H).

The synthetic route of 6274-50-6 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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Adding a certain compound to certain chemical reactions, such as: 63485-51-8, name is trans-Methyl 3-hydroxycyclobutanecarboxylate, 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 63485-51-8, Computed Properties of C6H10O3

The 3 – [(1 R) -1 – phenyl ethyl] imidazole -4 – carboxylic acid (1 A) (1.0 g, 4.6 mmol) suspended in dichloromethane (20 ml) in, adding trans -3 – hydroxy-cyclobutyl carboxylic acid methyl ester (2 A) (0.9 g, 6.9 mmol), 1 – (3 – dimethylamino propyl) -3 – ethyl carbodiimide hydrochloride (1.3 g, 6.9 mmol), 4 – dimethylamino pyridine (0.85 g, 6.9 mmol), stirring at room temperature for 2 hours. The reaction solution for sequentially saturated sodium dihydrogen phosphate aqueous solution (30 ml × 2) and saturated salt water (30 ml × 1) washing, drying of the organic phase with anhydrous sodium sulfate, filtered, the filtrate is concentrated under reduced pressure, the residue separation and purification with silica gel column chromatography (ethyl acetate/petroleum ether (v/v)=1/20 – 1/5), to obtain the title compound trans – (3 – methoxy carbonyl cyclobutyl) 3 – [(1 R) -1 – phenethyl] imidazole -4 – carboxylic acid ester (compound 2), colorless oily matter (1.0 g, yield 66percent)

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, trans-Methyl 3-hydroxycyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Qiu Guanpeng; Wei Yonggang; Lu Yonghua; Huang Qingping; Liao Pengfei; (17 pag.)CN107641105; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 25542-62-5, 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. 25542-62-5, name is Ethyl 6-bromohexanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The compound represented by Formula 8-a was synthesized by Reaction 8-1.Ethyl 2-methylacetatoacetate (23.5 g, 163 mmol) and ethyl 6-bromohexanoate (40.0 g, 179 mmol) were stirred in 200 ml of ethanol and liquid sodium ethoxide was added dropwise thereto. The mixture was stirred at 80 C. for 10 h. After completion of the reaction, the solid was filtered off. The filtrate was distilled under reduced pressure and extracted with dichloromethane and a 2 N aqueous solution of hydrochloric acid. The organic layer was treated with anhydrous sodium sulfate and distilled under reduced pressure (47.7 g). After removal of the solvent, 300 ml of water was added, followed by stirring under reflux for 10 h. After completion of the reaction, the reaction solution was extracted with dichloromethane, treated with sodium sulfate, and distilled under reduced pressure (25 g, 71%).1H NMR (400 MHz, CDCl3): delta=10.85 (1H, s), 2.52 (1H, m), 2.36 (2H, m) 2.30 (3H, s), 1.65 (4H, m), 1.35 (4H, m), 1.09 (3H, d)

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

Reference:
Patent; SFC CO., LTD.; Song, Ju-man; Min, Seon-Gi; Lee, Seung-Soo; Lee, Do-min; Park, Kyung-Hwa; Hwang, Moon-Chan; Shin, Bong-Ki; Je, Jong-Tae; (72 pag.)US10473666; (2019); B2;,
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Application of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-5-chloro-1,2-oxydiethylene-4-pyrazolin-3-one(300mg, 0.860mmol) in acetonitrile (12 mL ) was added potassium carbonate (300 mg, 2.15 mmol) and methyl-2-bromobutyrate (230muL, 1.72mmol) and the mixture was stirred at room temperature for 23 hours. After completion of the reaction, water (50mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50mL × 3). After drying the combined organic layers over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography – (ethyl acetate: methanol – Le = 9: 1) to give 5-chloro-4-(8-chloro-2-ethyl-6-fluoro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-5-yl)-1,2-oxydiethylene-4-pyrazolin-3-one white solid (231 mg, yield: 64%)

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; TATENO, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (76 pag.)JP2016/60742; (2016); 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 23426-63-3 as follows. Application In Synthesis of Methyl 2-bromo-2-methylpropanoate

To a solution of 2,3,5-trimethylphenol (20.0 g, 147 mmol) in dimethylsulfoxide (100 ml) was added methyl 2-bromoisobutyrate (52.2 g, 288 mmol) and potassium carbonate (40.0 g, 289 mmol) at room temperature. The mixture was stirred for 36 hours. The resulting mixture was poured into water and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified using basic silica gel column chromatography (hexane/ethyl acetate = 50/1) to obtain 30.3 g (yield 87 %) of oily title compound.1H-NMR (CDCl3) delta : 1.57 (6H, s), 2.11 (3H, s), 2.21 (6H, s), 3.79 (3H, s), 6.33 (1H, s), 6.46 (1H, s).

According to the analysis of related databases, 23426-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1411052; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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. name: Methyl trans-4-aminocyclohexanecarboxylate hydrochloride

To a stirred solution of 6-((1,6-naphthyridin-2-yl)amino)-4-(cyclopropylamino)nicotinic acid (1.85 g, 5.76 mmol, Intermediate N) and methyl (1R,4R)-4-aminocyclohexane-1-carboxylate hydrochloride (1.34 g, 6.91 mmol) in DMF (10 mL) was added DIPEA (5 mL, 28.8 mmol) and PyBOP (4.5 g, 8.64 mmol) at rt. The resulting reaction mixture was stirred at rt for 16 h. The reaction mixture was then transferred into ice water and the resulting precipitate was filtered off, and dried reduced pressure. The crude product was purified using silica gel column chromatography (7% MeOH-DCM) to give methyl (1r,4r)-4-(6-((1,6-naphthyridin-2-yl)amino)-4-(cyclopropylamino)nicotinamido)cyclohexane-1-carboxylate as light a green solid (1.3 g, 49%). LC-MS (ESI+) m/z 460.54 (M+H)+

The synthetic route of Methyl trans-4-aminocyclohexanecarboxylate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6627-89-0, These common heterocyclic compound, 6627-89-0, name is tert-Butyl phenyl carbonate, 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.

Example 36A; To a solution of 8.00 g (76.7 mmol) pentane-1 ,3-diamine in 150 ml anhydrous ethanol 29.0 ml (153 mmol) te/t-butyl-phenyl-carbonate are added. The mixture is heated to reflux for 4 h. After cooling to room temperature 500 ml water is added, the mixture is adjusted to pH 3 with 2M HCI and extracted two times with 500 ml DCM. The aqueous layer is separated, adjusted to pH 12 with 2M sodium hydroxide solution and extracted three times with 500 ml DCM. The organic phases are combined, dried and evaporated under reduced pressure to yield the product as an oil. The product is used for the next reaction without further purification, yield: 15.5 g (100%) LC-MS (Method 1s): RT = 0.91 min MS (ESI pos): m/z = 203 (M+H)+

The synthetic route of 6627-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/92566; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics