Month: March 2021

Reference of 105-53-3,Some common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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.

Under the protection of nitrogen, the 100g c diethyl malonate, 300 ml anhydrous ethanol into 1000 ml three port in round bottomed flask, under room temperature, adding 40.5g sodium methoxide, then, slowly adding 102.8g bromo n-butane, after adding heating reflux, the reaction 3h; to cool down to room temperature, then adding 40.5g sodium methoxide, then, slowly adding 102.8g bromo-butane, heating reflux reaction 3h. Cooling to room temperature, removing the solvent, by adding 1 mol/L sulfuric acid aqueous solution in the pH value and system to 7 the left and the right, washing the organic phase, is distilled under reduced pressure to obtain the dibutyl c diethyl malonate, 154g (yield 90.6%).

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Advanced Institute; Jiang Yang; Li Jiusheng; Xu Jian; (6 pag.)CN106748724; (2017); A;,
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Some common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, molecular formula is C15H31NO6, 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 tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate

107 mg (0.335 mmol) of tert-Butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate and 93 mg (0.369 mmol) of (2,5-dioxopyrrolidin-1-yl) 2-(2,5-dioxopyrrol-1-yl)acetate were dissolved in 5 ml of dimethylformamide, and 0.074 ml (0.671 mmol) of N-methylmorpholine were added. The reaction mixture was stirred at RT overnight. 0.048 ml (0.838 mmol) of acetic acid were added and the reaction mixture was purified directly by preparative RP-HPLC (column: Reprosil 125*30; 10mu, flow rate: 50 ml/min, MeCN/water/0.1% TFA). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 133 mg (86%, purity 100%) of tert-Butyl 3-[2-[2-[2-[2-[[2-(2,5-dioxopyrrol-1-yl)acetyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate. LC-MS (Method 1): Rt=0.82 min; MS (ESIpos): m/z=459 (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 581065-95-4, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; CANCHO GRANDE, Yolanda; WITTROCK, Sven; BERNDT, Sandra; GRITZAN, Uwe; FITTING, Jenny; STELTE-LUDWIG, Beatrix; JONES, Patrick; MAHLERT, Christoph; VOTSMEIER, Christian; SCHOeNFELD, Dorian; TRAUTWEIN, Mark; WEBER, Ernst; PAWLOWSKI, Nikolaus; GREVEN, Simone; GLUeCK, Julian Marius; HAMMER, Stefanie; DIETZ, Lisa; MAeRSCH, Stephan; (357 pag.)US2020/138970; (2020); 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. 91085-56-2, name is Ethyl 3,5-dichlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Ethyl 3,5-dichlorobenzoate

Ethyl 3,5-dichlorobenzoate (8.4 g, 38.3 mmol) and sodiumhydride (1.1 g, 46.0 mmol) were dissolved in 100 mL THF underN2. To the mixture was added 13.2 mL ethyl propionate slowly atroom temperature and refluxed overnight. The solvent wasremoved under reduced pressure. The residue was extracted withethyl acetate, washed with water and brine and dried over Na2SO4.Flash column chromatography gave 9.7 g (92%) ethyl 3-(3,5-dichlorophenyl)-2-methyl-3-oxopropanoate 5 as orange solid. 1HNMR (400 MHz, DMSO-d6) d 7.97 (t, J = 3.3 Hz, 3H), 4.80 (q, J =6.9 Hz, 1H), 4.07 (q, J = 7.1 Hz, 2H), 1.31 (d, J = 6.9 Hz, 3H), 1.08(t, J = 7.1 Hz, 3H). MS (ESI, m/z): 274.0 [MH].

The synthetic route of 91085-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shu, Shuangjie; Dai, Antao; Wang, Jiang; Wang, Bin; Feng, Yang; Li, Jia; Cai, Xiaoqing; Yang, Dehua; Ma, Dakota; Wang, Ming-Wei; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1896 – 1908;,
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Application of 4934-99-0, 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. 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of oxalyl chloride (5.25 mL, 60.0 mmol) in DCM (200 ml) at -78 C. was added DMSO (7.10 mL, 100 mmol). After 30 minutes, a solution of methyl 3-hydroxycyclobutanecarboxylate (6.51 g, 50 mmol) in methylene chloride (50 mL) was added. The mixture was stirred for 30 minutes at -78 C. and TEA (27.9 mL, 200 mmol) was then added. The mixture was allowed to warm to room temperature over 2 hours. To the reaction mixture was then added water and the layers separated. The organic phase was washed with water, dried over Na2SO4 and concentrated to give product (quantitative yield). 1H NMR (400 MHz, CDCl3): 3.14-3.32 (m, 3H) 3.32-3.46 (m, 2H) 3.73 (s, 3H)

The chemical industry reduces the impact on the environment during synthesis Methyl 3-hydroxycyclobutanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Novartis AG; FU, Jiping; JIN, Xianming; KARUR, Subramanian; LAPOINTE, Guillaume; MADERA, Ann Marie; SWEENEY, Zachary Kevin; (45 pag.)US2016/166548; (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. 42726-73-8, name is tert-Butyl methyl malonate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

9.91 Gram (95percent, 56.9 mmol) of tert-butyl methyl malonate was dissolved in 120 mL of tetrahydrofuran (THF), and the resulting solution was added dropwise to a suspension containing 2.28 g (60 wtpercent, 56.9 mmol) of sodium hydride (NaH) and 120 mL of THF at 0¡ãC over 0.5 hours, followed by stirring for 0.5 hours. Thereafter, a solution containing 8.08 g (56.9 mmol) of methyl iodide (Mel) and 20 mL of THF was added dropwise over 0.5 hours, and the resulting mixture was stirred at 0¡ãC for 0.5 hours and further stirred at 25¡ãC for 5 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in order, twice with saturated brine and twice with water, and dried over sodium sulfate, and the solvent was concentrated to obtain 13.0 g of 1-tert-butyl 3-methyl 2-methylmalonate as a colorless transparent oil. Subsequently, 45.9 g of an aqueous formalin solution was added to 13.0 g of the oil, and resulting mixture was cooled to 0¡ãC. Furthermore, 7.81 g of potassium carbonate was added, and the mixture was stirred at 0¡ãC for 1 hour and further stirred at 25¡ãC for 3 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in order, three times with an aqueous saturated sodium hydrogensulfite solution and twice with water, and dried over sodium sulfate. The solvent was concentrated, and the residue was dissolved in 50 mL of pyridine. The resulting solution was cooled to 0¡ãC, and 21.7 g of p-toluenesulfonyl chloride was added thereto. The obtained mixture was stirred at 0¡ãC for 2 hours and then stirred at 60¡ãC for 4 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in order, three times with an aqueous saturated ammonium chloride solution and twice with water, and dried over sodium sulfate. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate=4/1) to obtain 15.8 g of the objective Compound (I-31) as a colorless transparent oil. 1H-NMR (400 MHz, CDCl3) delta 1.40 (s, 9H), 1.43 (s, 3H), 2.45 (s, 3H), 3.67 (s, 3H), 4.30 (s, 2H), 7.36 (d, 2H), 7.77 (d, 2H).

The synthetic route of 42726-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujifilm Corporation; EP2177506; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, A new synthetic method of this compound is introduced below., Formula: C13H27NO5

A solution of 2-(2,6-dioxopiperidin-3-yl)-4- fluoroisoindoline- 1 ,3-dione (100 mg, 0.362 mmol), tert-butyl 3-(2-(2-(2-aminoethoxy)ethoxy) ethoxy)propanoate (100 mg, 0.362 mmol) and DIPEA (0.5 ml) in DMF (5 ml) was heated at 100 C overnight. After the starting materials were consumed, the reaction was concentratedunder reduced pressure. The resulting residue was purified by prep-HPLC to yield the product(72 mg, 37%) as yellow solid. ?H NMR (600 MHz, CD3OD) oe 7.55 (dd, J 7.1, 8.6 Hz, 1H),7.10 (d, J 8.5 Hz, 1H), 7.05 (d, J 7.0 Hz, 1H), 5.06 (dd, J= 5.4, 12.4 Hz, 1H), 4.10 (q, J=7.1 Hz, 1H), 3.72 (t, J 5.3 Hz, 2H), 3.69-3.59 (m, 8H), 3.59-3.55 (m, 2H), 3.50 (t, J= 5.3Hz, 2H), 2.91 -2.82 (m, 1H), 2.78-2.68 (m, 2H), 2.45 (t, J= 6.2 Hz, 2H), 1.43 (s, 9H). HRMS(ESI-TOF) m/z: [M+Hj calculated for C26H36N309, 534.2446; found: 534.2459.

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; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; JIN, Jian; YANG, Xiaobao; LIU, Jing; XIONG, Yan; POULIKAKOS, Poulikos; KAROULIA, Zoi; WU, Xuewei; AHMED, Tamer; (199 pag.)WO2018/106870; (2018); A1;,
Ester – Wikipedia,
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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 42122-44-1 as follows. category: esters-buliding-blocks

Example 2.42- (4-Fluoro-phenvl)-6-methanesulfonvl-3- (4-methanesulfonyl-phenyl)-pyrazolof 1. 5-blpvridazine(i) 2- (4-Fluoro-phenvl)-6-methvlsulfanvl-pyrazolo1, 5-blpvridazine-3-carboxvlic acid methyl ester Solidt-butoxycarbonyl-O-mesitylenesulfonylhydroxylamine’ (7. 8g) was added portionwise with stirring to TFA (25mL) over 10min then stirred for a further 20 minutes. The solution was poured onto ice(-200mL) and left until the ice melted. The resulting white solid was filtered off, washed with water, and dissolved in DME(100mL). The solution was dried over 4A mol. sieves for 1.5 hours, filtered then added to a solution of3-methylthio-pyridazine2 (2.6g) indichloromethane (35mL) and the reaction stirred at room temperature for 20h. The intermediate salt was isolated by filtration as light brown crystals (3. 87g), suspended in acetonitrile(100mL) and methyl3- (4-fluoro-phenyl)-prop-2-ynoic acid (2. 02g) added. 1,8- Diazabicyclo [5.4. 0] undec-7-ene (2. 1mL) was added dropwise and the reaction was stirred at room temperature for 20 hours. The resulting crystalline precipitate was filtered off, washed and dried (770mg). Concentration of the filtrate gave a second crop (430mg). The residues were partioned between water and ethyl acetate(100mL each) and the aqueous layer was extracted with ethyl acetate (20mL). The combined organics were washed with water, brine and dried. Removal of solvent gave a brown oil which was purified by flash chromatography on silica (300g) eluting with cyclohexane/ethyl acetate (3: 1) to give a further quantity of product (247mg). The three crops were combined to give the title compound (1.45g) as a light brown solid.

According to the analysis of related databases, 42122-44-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/48999; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 174403-69-1, name is Methyl 4-fluoro-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 4-fluoro-2-methylbenzoate

Methyl 4-fluoro-2-methylbenzoate (2.00 g, 11.9 mmol) and butanenitrile (3.1 ml, 36 mmol) are placed in a flask placed under argon and were dissolved in THF (30 ml, 370 mmol). The solution was cooled with a water bath to keep the reaction at room temperature. To this solution lithium 1,1 ,1,3,3,3-hexamethyldisilazan-2-ide (37 ml, 1.0 M, 37 mmol) was slowly added over 10 minutes. Water and ethyl acetate were added, the mixture was subsequently stirred for 10 minutes and acidicfied with aqueous hydrochloric acid. The mixture was three times extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate and concentrated. The crude product (quant.) was used without any further purification in the next step. LC-MS (method 9): Rt = 1.25 min; MS (ESIpos): m/z = 206 [M+H]+

The synthetic route of 174403-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; KLAR, Juergen; EHRMANN, Alexander; WILLWACHER, Jens; ENGEL, David; DIESKAU, Andre Philippe; KAHNERT, Antje; GROMOV, Alexey; SCHMECK, Carsten; LINDNER, Niels; MUeLLER, Thomas; ANDREEVSKI, Anna Lena; DREHER, Jan; COLLINS, Karl; (861 pag.)WO2018/69222; (2018); 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. 10602-06-9, name is Methyl 3-ethynylbenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C10H8O2

General procedure: The alkyne (6 or 7, 1.24 mmol) was dissolved in tert-butanol(10 mL) and added to a water solution (10 ml) of N,N-Dimethyl-N-(3-azidopropyl)amine hydrochloride(226 mg, 1.37 mmol), copper (II) sulphate pentahydrate (31 mg, 10% mol) and sodium ascorbate (246 mg,1.24 mmol). The resulting mixture was stirred for 24 h, at r.t. The organic solvent was removed undervacuum and the residue was diluted with saturated NaHCO3 (10 mL) and extracted with DCM(3 x 20 mL). The combined organic phases were dried over Na2SO4 and the solvent was removedunder reduced pressure. The crude was purified by flash chromatography (CHCl3/MeOH 95:5).

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; Tassinari, Martina; Lena, Alberto; Butovskaya, Elena; Pirota, Valentina; Nadai, Matteo; Freccero, Mauro; Doria, Filippo; Richter, Sara N.; Molecules; vol. 23; 8; (2018);,
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Adding a certain compound to certain chemical reactions, such as: 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, 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 18469-52-8, Recommanded Product: 18469-52-8

General procedure: To a solution of acid 3 (1.25 g, 3.1 mmol), HBTU (1.6 g, 3.7 mmol),and Et3N (10 mL) in 20 mL acetonitrile was added 1.2 equimolaramount of the appropriate amine. The mixture was kept stirring atroom temperature for 5 h. TLC detection found that the reactionwas complete, then the mixture was evaporated under reducedpressure to remove solvent. The residue was taken up saturatedsodium chloride and 1mL 3 N HCl and extracted with ethyl acetate(30 mL x 3), and the combined organic layers were washed twotimes with saturated sodium chloride and 1mL 3 N HCl. Theorganic layers were dried (MgSO4), filtered, and solvent wasremoved under reduced pressure at 40 C to give the crude product,which was purified by column chromatography to produce thecorresponding intermediate, 4 and 7.

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

Reference:
Article; Jia, Ruifang; Zhang, Jian; Ai, Wei; Ding, Xiao; Desta, Samuel; Sun, Lin; Sun, Zhuosen; Ma, Xiuli; Li, Zhong; Wang, Defeng; Huang, Bing; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 64 – 80;,
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