Month: September 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. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H7FO4

2-Hydroxy-3-fluoro-8,8-dimethyl-6,7,8,9-tetrahydro-4H-pyrimido[1 ,2- a]pyrimidin-4-one can be prepared in the following way. A suspension of 5 g of 4,4-dimethyl-1 ,4,5,6-tetrahydropyrimidin-2- amine, 29 g of dimethyl fluoromalonate and 3.9 g of sodium methoxide is heated at 100C for 3 hours. The reaction medium is concentrated to dryness under reduced pressure. The residue obtained is taken up with ethyl ether. The solid formed is filtered off and then dried. 10 ml of water are added to the solid obtained, and the resulting mixture is cooled on ice, before acidification to pH 5-6 by adding concentrated hydrochloric acid (25%). The suspension is filtered and then the solid is washed with 5 ml of water and then dried under vacuum over P2O5, so as to give 3.15 g of 2-Hydroxy-3-fluoro-8,8-dimethyl- 6,7,8,9-tetrahydro-4H-pyrimido[1 ,2-a]pyrimidin-4-one, in the form of a yellow powder, the characteristics of which are the following: Mass spectrum (method A) (ES+/-) [M+H]+: m/z 232; [M-H]-: m/z 230; Tr (min) = 0.86

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 344-14-9.

Reference:
Patent; SANOFI; EL-AHMAD, Youssef; FILOCHE-ROMME, Bruno; LETALLEC, Jean-Philippe; MARCINIAK, Gilbert; RONAN, Baptiste; VIVET, Bertrand; WO2013/190510; (2013); A2;,
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Synthetic Route of 344-14-9, 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 344-14-9 as follows.

Part A: 5-Fluoro-2-(fluoromethyl)-6-hydroxy-4(1 H)-pyrimidinone 2-Fluoro-acetamidine hydrochloride salt (1 1 .2 g, 100 mmol) and dimethyl fluoromalonate (15 g, 100 mmol) in anhydrous methanol (300 mL) were treated with solid NaOMe (16.2 g, 300 mmol) and heated to 50 C with stirring. When LCMS showed formation of the desired product, the solvent was evaporated to dryness, and the residue was neutralized with concentrated HCI (20 mL). The white precipitate was collected by filtration to give 5-fluoro-2-(fluoromethyl)-6-hydroxy-4(1 H)-pyrimidinone (100% yield). LCMS: (M+H)+: 163.1.

According to the analysis of related databases, 344-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
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Electric Literature of 1014645-87-4,Some common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, molecular formula is C11H14ClNO2, 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.

General procedure: To a solution of selected acid (1 eq) in DMF, HCTU (1.1 eq) and DIPEA (2.5 eq) were added in sequence and the resulting mixture was stirred 30 min before adding the selected amine (1.1 eq). The mixture was left stirring at RT for 1-18 hrs then the reaction mixture was partitioned between EtOAc and H2O and the organic phase was separated. The aqueous phase was washed with EtOAc. All the collected organic phases were washed with NaCl sat. sol., dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified on SPE-Si cartridge or Biotage SNAP-Si column eluting with a mixture of DCM/EtOAc from 100:0 to 95:5 affording the title amide compound. The title compound (D58) (250 mg) was prepared according to the general procedure for amides preparation (Method C) starting from 1-(tert-butoxycarbonyl)-4,4-dimethylpiperidine-2-carboxylic acid (320 mg; described in J. Med. Chem. 1997, 40, 2491-2501) and methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (312 mg). Reaction time: 18 hrsMS: (ES/+) m/z: 431.4 [MH+] C24H34N2O5 requires 430.251H NMR (400 MHz, CHCl3-d) delta (ppm): 7.96 (d, J=8.2 Hz, 2H), 7.32-7.29 (m, 2H), 6.82-6.59 (m, 1H), 4.65 (d, J=4.4 Hz, 1H), 4.02 (br. s., 1H), 3.92 (s, 3H), 3.00 (d, J=10.6 Hz, 1H), 2.18 (d, J=12.9 Hz, 1H), 1.50 (s, 9H), 1.43-1.29 (m, 7H), 0.96 (s, 3H), 0.84 (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 Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, its application will become more common.

Reference:
Patent; Borriello, Manuela; Pucci, Sabrina; Stasi, Luigi Piero; Rovati, Lucio; US2015/87626; (2015); 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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, A new synthetic method of this compound is introduced below., Formula: C5H10O4

Preparation of substituted 3-hydroxy isoquinolines were carried out in the manner described in Fukumi, H.; Kurihara, H.; Heterocycles., 1978, 9(9), 1197-1205. Thus, a mixture of 4-methyl benzylamine (5.54 g, 45.7 mmol) and methyl dimethoxyacetate (6.17 mL, 50.3 mmol) was heated to 130 C. where it stirred for 4 h. After this time, the volatiles were removed under reduced pressure to provide a residue. The residue was azeotroped to dryness from toluene to provide the product, which was used directly in the next step without further purification. MS (E+) m/z: 224 (MH+); LC retention time (Method A): 2.49 min.

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; Weinstein, David S.; Gilmore, John L.; Sheppeck, James; Yang, Bingwei Vera; Kim, Soong-Hoon; Vaccaro, Wayne; US2005/187242; (2005); A1;,
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Synthetic Route of 29263-94-3, 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the compound of Reference Example 61 (176 g) in tetrahydrofuran (1000 ml) were addded tetrakistriphenylphosphine palladium (2.21 g) and morpholine (200 g), and the mixture was stirred at room temperature. Twenty-five minutes later, to the reaction solution were added a 5 % aqueous potassium hydrogen sulfate solution and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2-methyl-2-propanyl (3R)-3-{[(4-hydroxy-2-methyl-5-nitrophenyl)carbonyl](2-propanyl)amino}-1-piperidinecarboxylate (156 g). To a solution of the obtained 2-methyl-2-propanyl (3R)-3-{[(4-hydroxy-2-methyl-5-nitrophenyl)carbonyl](2-propanyl)amino}-1-piperidinecarboxylate (138 g) in N,N-dimethylformamide (1000 ml) were added potassium carbonate (91 g), diethyl 2-bromo-2-methylmalonate (94 g), and the mixture was stirred at 80C for 8 hours. The reaction solution was allowed to cool to room temperature, filtered through celite, and to the filtrate were added a 5 % aqueous sodium hydrogen sulfate solution and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g). Subsequently, to a suspension of iron (110 g) in acetic acid (500 ml) was added dropwise a solution of the obtained diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g) in acetic acid (200 ml) slowly at 90C. Ten hours later, the mixture was allowed to cool to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to give the title compound (102 g). Rf = 0.25 (n-hexane/ethyl acetate=1/1)

The chemical industry reduces the impact on the environment during synthesis Diethyl 2-bromo-2-methylmalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP2447264; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 59247-47-1,Some common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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 tert-butyl 4-bromobenzoate (616 mg, 2.4 mmol) in 1,4-dioxane and water (4:1, 10 mL) were added (E)-4,4,5,5-tetramethyl-2-styryl-1,3,2-dioxaborolane (553 mg, 2.4 mmol), tetrakis(triphenylphosphine)palladium (58.9 mg, 0.05 mmol) and sodium carbonate (164 mg, 1.55 mmol). The mixture was stirred at 90° C. under nitrogen atmosphere for 18 hours. Once the start material was consumed, the resultant mixture was concentrated to give a residue and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=30:1) to give tert-butyl 4-(1-phenylvinyl)benzoate (0.59 g, 87.5percent). 1H NMR (300 MHz, CDCl3): delta 7.96 (d, J=4.8 Hz, 2H), 7.41-7.26 (m, 7H), 5.55-5.53 (m, 2H), 1.61 (s, 9H).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US9206128; (2015); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 87-24-1, 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. 87-24-1 name is Ethyl 2-methylbenzoate, 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 A 9,10-Dihydrophenanthrene-1-methanol A stirred mixture of ethyl 2-methylbenzoate (30 grams, 0.183 mole) and N-bromosuccinimide (35 grams, 0.194 mole) in carbon tetrachloride (200 ml) was irradiated with an infrared lamp and heated at reflux for 20 minutes. The reaction mixture was allowed to cool to room temperature, then filtered. The filtrate was evaporated under reduced pressure to give ethyl 2-bromomethylbenzoate as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; FMC Corporation; US4451484; (1984); A;; ; Patent; FMC Corporation; US4507317; (1985); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1462-12-0, name is Diethyl 2-ethylidenemalonate, molecular formula is C9H14O4, 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. Safety of Diethyl 2-ethylidenemalonate

General procedure: In the following three cases, Ia-1, Ia-2, and Ia-3 were used as free radical precursors, and reacted with Michael acceptor IIa to obtain addition product IIIa. The same reaction conditions were used: base K2HPO4, photocatalyst [Ir(ppy)2(dtbbpy)]PF6 (1 mol%),Solvent THF (concentration: 0.2 M), light source 8W blue LED strip, reaction temperature 40 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1462-12-0, its application will become more common.

Reference:
Patent; Sichuan University; Song Hao; Qin Yong; Xue Fei; Liu Xiaoyu; Zhang Dan; Wang Falu; Liu Jiazhen; Di Jiamei; Liao Qi; Lu Huifang; Zhu Min; He Liping; (29 pag.)CN108456156; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, 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 88709-17-5, name: Ethyl 2-ethoxy-4-methylbenzoate

To the reaction kettle were added ethyl 4-methyl-2-ethoxybenzoate (2.08 g, 10 mmol), ethanol (23 g, 0.50 mol), tetrahydrofuran (100 mL), and tert-peroxybutyl ether (1.75 g, 10 mmol) in this order. , PdCl2 (54.3 mg, 0.3 mmol) and 1,2-bis (di-2-pyridylphosphine) ethane (123.3 mg, 0.3 mmol), charged with 2.0 MPa of CO, heated to reflux, and stirred for 20 hours. After cooling to room temperature, a 2 mol / L sodium hydroxide aqueous solution (30 mL) was added to the reaction solution after depressurization. After stirring for 6 hours, cyclohexane (50 mL × 3) was added to wash the reaction solution. The reaction solution was neutralized with hydrochloric acid to a pH of 7, The solution was concentrated under pressure to about 50 mL, hydrochloric acid was acidified to pH 3, a yellow solid was precipitated, and the residue was recrystallized from toluene-petroleum ether to obtain a white solid intermediate (I) (1.94 g, yield: 76.9%).

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; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Yu Rui; Hong Xuming; Zheng Min; Shao Qingling; (8 pag.)CN110483292; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6138-26-7,Some common heterocyclic compound, 6138-26-7, name is Trimethyl propane-1,2,3-tricarboxylate, molecular formula is C9H14O6, 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.

In a reactor equipped with a stirrer, a thermometer, a condensing tube, and a Dean-Stark trap, 4-hydroxy-2,2,6,6-tetramethylpiperidine (4.32 g), 1,2,3-propanetricarboxylic acid trimethyl ester (2.00 g), and dibutyl tin oxide (0.28 g) were dissolved in xylene (28 mL), and the resulting solution was refluxed under heating for 48 hours in a nitrogen atmosphere. During the course, generated methanol was removed by molecular sieves. The resulting product was cooled to room temperature and then washed by adding water. The resulting product was purified by recrystallization, and (I-1-a) was obtained as colorless powder. The yield was 1.12 g. The melting point was 110 C.1H-NMR (400 MHz, CDCl3): 1.05-1.16 (m, 24H), 1.21 (s, 18H), 1.87-1.92 (m, 6H), 2.54 (dd, J=6.2 Hz, 16.6 Hz, 2H), 2.70 (dd, J=7.1 Hz, 16.6 Hz, 2H), 3.16-3.23 (m, 1H), 5.13-5.23 (m, 3H).GC-MS (EI): m/z 594 [M+H+], 578 [M-15+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Trimethyl propane-1,2,3-tricarboxylate, its application will become more common.

Reference:
Patent; DIC CORPORATION; Iwakubo, Masayuki; Nose, Sayaka; Takachi, Manabu; Aoki, Yoshio; (13 pag.)US10336939; (2019); B2;,
Ester – Wikipedia,
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