Month: June 2021

Synthetic Route of 1132-95-2, 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 1132-95-2 as follows.

The compound (103 mg) produced in production step 11-1 was dissolved in 2.0 mL of N,N-dimethylformamide. Cyclohexanone di-i-propyl acetal (58 muL) and 12.4 mg of p-toluenesulfonic acid were added to the solution, and the mixture was allowed to react at room temperature for one hr. A saturated aqueous sodium bicarbonate solution (20 mL) was added thereto, and the resultant precipitate was collected by filtration, was washed with water, and was dried under the reduced pressure to give the title compound (103 mg, 88%). Rf value: 0.53 (chloroform: methanol = 10: 1) ESIMS: m/z 1171 [M + Na]+

According to the analysis of related databases, 1132-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Meiji Seika Kaisha Ltd.; Microbial Chemistry Research Foundation; EP2036917; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 35180-01-9 as follows. Recommanded Product: Chloromethyl isopropyl carbonate

Step 1. Preparation of Iodomethylisopropyl carbonate: Tea solution of anhydrous sodium iodide (6 g, 40 mmol) in anhydrous acetonitrile (20 mL) chloromethyl isopropyl carbonate (2.9 g, 19 mmol) in anhydrous, acetonitrile (10 mL) was added drop wise over 20 min. The reaction mixture, covered with aluminum foil (protected from light) was stirred at room temperature overnight. The solid separated was filtered, washed with acetonitrile and the filtrate was concentrated under reduced pressure. Residue was dissolved in water (10 mL) and organics were extracted in ether (25 mL). Ether extracts were washed with sodium bisulfite (5%, 10 mL), later brine (10 mL). Organic layer was dried over anhydrous, sodium, sulfate, filtered, concentrated and dried under high dried vacuum. Yield 2.72 g (58%); 1H-NMR delta 1.3 (d, 6H), 4.95 (m, 1H), 5.95 (s, 2H).

According to the analysis of related databases, 35180-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPRING BANK PHARMACEUTICALS, INC.; Iyer, Radhakrishnan P.; Coughlin, John Edward; (35 pag.)US2015/329864; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 99548-55-7, name is Methyl 4-bromo-2-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 99548-55-7, COA of Formula: C9H9BrO2

General procedure: A mixture of methyl 5-fluoro-2-methylbenzoate (0.5 g, 3.0 mmol),NBS (0.18 g, 3.0 mmol), and di-benzoyl peroxide (BPO) (36 mg, 0.15 mmol) in 1,2-dichloroethane (5 mL) was heated at 80 C for 12 huntil all starting material was consumed. The reaction was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give a crude product (0.65 g, 89%), which was used in the next step reaction without further purification.

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, Methyl 4-bromo-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Huang, Junli; Deng, Xiaoyan; Zhou, Siru; Wang, Na; Qin, Yujun; Meng, Liuwei; Li, Guobao; Xiong, Yuhua; Fan, Yating; Guo, Ling; Lan, Danni; Xing, Junhao; Jiang, Weizhe; Li, Qing; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 644 – 654;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 142166-01-6, name is Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate, molecular formula is C10H11NO3, 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. Computed Properties of C10H11NO3

Step 3: 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (1 g, 5.2 mmol) was dissolved in MeOH (5 ml) and THF (10 ml) in a 25 mL flask, to which LiOH (2 g) dissolved in H2O (5 ml) was added, followed by stirring at room temperature for 12 hours. Upon completion of the reaction, the solvent was concentrated. The pH of the reaction mixture was adjusted to 5 by using 2N HCl. The mixture was extracted with EA. The organic layer was dried over MgSO4 and filtered. As a result, 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid was obtained (1.2 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 142166-01-6, its application will become more common.

Reference:
Patent; Hyundai Pharm Co., Ltd.; LEE, In Hee; CHAE, Hee Il; KIM, Se hoan; MOON, Soon Young; HA, Tae Young; CHOI, Hyo sun; KIM, Young Seok; KIM, Chun hwa; RHEE, Jae Keol; (132 pag.)US2016/355483; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-amino-4-methoxylbenzoate

To a solution of compound 1 (50 g, 276 mmol) in CHCb (600 mL) was added SO2CI2 (26 mL, 331 mmol) in an ice bath and stirred at reflux for 4 hours. The reaction mixture was concentrated to afford the crude product, which was purified by trituration with PE/EA = 1 : 1 (200 mL) to get desired product as white solid (36 g, 61% yield). 1H MR (400 MHz, DMSO-d6) delta: 7.64 (IH, s), 6.48 (IH, s), 3.81 (3H, s), 3.75 (3H, s).

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 50413-30-4.

Reference:
Patent; CEREPEUT, INC.; LU, Bingwei; (43 pag.)WO2019/55528; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 606-45-1, name is Methyl 2-methoxybenzoate, 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 606-45-1, category: esters-buliding-blocks

General procedure: Various benzohydrazides 5-7 and 9-13 were obtained accordingto known procedures [40,65] except for benzohydrazides 4and 8 which were commercially available. A solution of the methylbenzoate (1 equiv) in ethanol was added dropwise to 65% hydrazinemonohydrate (5 equiv). The reaction mixture was then heatedunder reflux and stirred overnight. The reaction progress was followedup by TLC. Crude product was collected by filtration aftercooling of the reaction medium and finally washed with coldethanol unless specified otherwise. The desired benzohydrazides were used without any further purification.The analysis of spectral data (1H and 13C NMR), the yields, HRMS,Mp and Rf of these precursors are presented in SupplementaryInformation.

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

Reference:
Article; Ameryckx, Alice; Thabault, Leopold; Pochet, Lionel; Leimanis, Serge; Poupaert, Jacques H.; Wouters, Johan; Joris, Bernard; Van Bambeke, Francoise; Frederick, Raphael; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 324 – 338;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6624-71-1,Some common heterocyclic compound, 6624-71-1, name is Dodecyl isobutyrate, molecular formula is C16H32O2, 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 I Dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate STR7 To a solution of diisopropylamine (5.56 g, 0.055 mole) in 200 ml of dry ether at 0 C. under nitrogen is added with stirring n-butyllithium (0.055 mole) in hexane (31 ml). The resulting mixture is cooled to -70 C., and a solution of dodecyl isobutyrate (12.8 g, 0.05 mole) in ether (25 ml) is added dropwise over a period of 20 minutes. The mixture is warmed to -15 C., and a solution of 2,3-butanedione (4.73 g, 0.055 mole) in ether (10 ml) is added rapidly. The mixture then is stirred at -5 C. for 15 minutes. The reaction mixture is combined with 200 ml of saturated ammonium chloride solution, and the separated organic layer is washed in sequence with 200 ml of 0.5N HCl, 200 ml of saturated sodium bicarbonate, and 200 ml of saturated sodium chloride. The solution is dried over magnesium sulfate and the solvent is removed under reduced pressure to give 19 g of an oil. The oil is distilled in a Kugelrohr apparatus (air bath temperature 85-115 C. at 0.1 mm Hg) to provide 13.5 g of almost pure product. Fractional distillation of the oil yields 11.5 g of pure product (67%), b.p. 132-133 C. at 0.05 mm Hg. IR and NMR data confirm the above structure. Anal. calc. for C20 H38 O4: C, 70.13; H, 11.18. Found: C, 70.11; H, 11.24.

The synthetic route of 6624-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Philip Morris Incorporated; US4701282; (1987); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2967-93-3, name is Methyl 2-fluoro-5-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 2967-93-3, Computed Properties of C9H9FO2

The 2-fluoro-5-methyl benzoic acid methyl ester (100 mg, 0 . 60mmol), NBS (112 mg, 0 . 63mmol), AIBN (60 mg, 0 . 36mmol) is added in the reaction bottle, by adding CCl4(5 ml), Ar atmosphere reflow 3h, raw material a small amount of residual, reducing pressure and evaporating solvent, adding anhydrous ethyl ether (10 ml), vacuum filtration, filtrate turns on lathe does, column chromatography, to obtain 20 mg of white solid, yield 13.5%.

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, Methyl 2-fluoro-5-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Institute Of Materia Medica Chinese Academy Of Medical Sciences; Xu, Bailing; Chen, Xiaoguang; Yao, Haiping; Ji, Ming; Jin, Jing; Zhou, Jie; Wang, Ke; Zhao, Dalong; (55 pag.)CN105461697; (2016); A;,
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. 6279-86-3, name is Triethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C10H16O6

Example 2N-r(7-hvdroxy-5-oxo-4,5-dihvdropyrazolori,5-alpyrimidin-6-yl)carbonyllglvcine A mixture of lH-pyrazol-5-amine (0.20 g, 2.40 mmol), triethyl methanetricarboxylate (0.51 mL, 2.40 mmol), glycine (0.27 g, 3.60 mmol) and l,8-diazabicyclo[5.4.0]undec-7-ene (0.68 mL, 4.80 mmol) in ethanol (5.0 mL) was heated to 180 0C for 20 minutes in a Biotage Initiator microwave synthesizer. The mixture was purified via preparative HPLC (YMC 75 X 30 mm column, 0.1% TFA in water and 0.1% TFA in acetonitrile) to afford the title compound as a yellow solid (0.065 g, 11%). 1H NMR (400 MHz, OMSO-d6) delta ppm 13.0 (s, 2 H) 9.87 (t, J=5.6 Hz, 1 H) 7.85 (d, J=2.0 Hz, 1 H) 6.01 (d, J=LO Hz, 1 H) 4.16 (d, J=5.8 Hz, 2 H). MS(ES+) m/e 253 [M+H]+.

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; SMITHKLINE BEECHAM CORPORATION; WO2009/39323; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18595-18-1, name is Methyl 3-amino-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 18595-18-1, Quality Control of Methyl 3-amino-4-methylbenzoate

To a suspension of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (4.09 g, 25.3 mmol) in dichloromethane (100 mL) and DMF (0.25 mL) at 0 C was added oxalyl chloride (4.15 mL, 48.0 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and stirred until complete conversion was detected by LCMS. The reaction was subsequently reduced to dryness and suspended in dichloromethane (100 mL) and was added a solution of methyl 3-amino-4-methylbenzoate (2) (4.6 g, 27.9 mmol) in dichloromethane (100 mL) and triethylamine (7.1 mL) . Contents were stirred at room temperature for 4 hours and diluted with dichloromethane (100 mL). The reaction was washed with water, saturated NaHC03, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude solid was triturated with diethyl ether to remove excess aniline and dried to afford methyl 3-(imidazo[1 ,2-a]pyridine-3-carboxamido)-4- methylbenzoate (3) as a white solid. MS m/z 310.1 (M+1 ) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-4-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics