Month: October 2020

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 3196-15-4 as follows. 3196-15-4

Step 4: methyl 2-(6-(azetidin-1-carbonyl)-2-((4-methylbenzoyl)imino)benzo[d]thiazol-3(2H)-yl)butanoate To a solution of N-(6-(azetidin-1-carbonyl)benzo[d]thiazol-2(3H)-ylidene)-4-methylbenzamide (91 mg, 0.26 mmol), prepared in Step 3, in N,N-dimethylformamide (1.0 mL) were added potassium carbonate (108 mg, 0.78 mmol) and methyl 2-bromobutyrate (45 uL, 0.39 mmol). The reaction mixture was stirred at 80 C. overnight and then cooled to room temperature. The reaction mixture was and quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. Diisopropyl ether and ethyl acetate were added to the filtrate. The resulting mixture was stirred for 5 minutes and then filtered. The resulting solid was washed with diisopropyl ether, and then dried under reduced pressure to give 61 mg of the titled compound as a white solid (Yield: 52%). 1H NMR (CDCl3, 400 MHz) delta 8.18 (d, 2H), 8.01 (s, 1H), 7.73-7.88 (m, 2H), 7.26-7.31 (m, 2H), 5.54-5.62 (m, 1H), 4.27-4.38 (m, 3H), 3.66 (s, 3H), 3.13 (m, 1H), 2.37-2.54 (m, 7H), 0.90 (t, 3H)

According to the analysis of related databases, 3196-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUHAN CORPORATION; Hur, Youn; Kim, Dong-Hyun; Kim, Eun-Kyung; Park, Jin-Hwi; Joo, Jae-Eun; Kang, Ho-Woong; Oh, Se-Woong; Kim, Dong-Kyun; Ahn, Kyoung-Kyu; US2015/11528; (2015); A1;,
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349-43-9, A common heterocyclic compound, 349-43-9, name is Ethyl 2-fluoropropionate, molecular formula is C5H9FO2, 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.

LDA (2.0 M, 36 mL) was added to the solution of ethyl 2- fluoropropanate (7.23 g) and acetaldehyde (13.5 mL) in ether (100 mL) at-78 ¡ãC. After the addition finished the reaction flask was kept in ice bath and gradually warm to room temperature. The reaction was quenched with aqueous ammonium chloride after overnight stirring. The aqueous phase was extracted with ether and the combined organic phase was dried over sodium sulfate. The solvent was stripped off and the residue was distilled in vacuo to give 541-YJ-97 (4.22 g).

The synthetic route of 349-43-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI CO. LTD.; WO2003/76424; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, molecular formula is C7H15NO2, 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. 5616-81-9

B. Synthesis of Intermediate B5 Intermediate B5 was synthesized using the method reported in Bioorganic & Medicinal Chemistry Letters 2008, 18, 3902-3905, with modifications as shown in the above scheme. Observed ESI HRMS: m/z 992.3193 [M+H]+. The 1H NMR spectrum of B5 is shown in FIG. 42a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5616-81-9, its application will become more common.

Reference:
Patent; Sirenas LLC; MACHERLA, Venkat Rami Reddy; SCHAMMEL, Alexander Wayne; USUI, Ippei; STOUT, Elizabeth Paige; BEVERAGE, Jacob Neal; LEE, Bryan Junn; COHEN, Steven Bruce; (304 pag.)US2017/15710; (2017); A1;,
Ester – Wikipedia,
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A common compound: 106614-28-2, name is Methyl 2,4-difluorobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 106614-28-2

To a three-necked flask was added 100 g of 5-hydroxy-7-azaindole (746 mmol), 141 g of methyl 2,4-difluorobenzoate(821 mmol), 237 g of potassium phosphate (1.12 mol) and 500 mL of diethylene glycol dimethyl Ether, 110 C for 24 h (HPLC to monitor 5-hydroxy-7-azaindole).The reaction solution was concentrated to dryness, and 2L of ethyl acetate and 2 L of water were added. The organic phase was separated,dried over anhydrous sodium sulfate, and concentrated to dry crude.The crude product was heated to reflux with 1260 mL of ethyl acetate. The mixture was slowly added dropwise to a solution of 1260 mL ofpetroleum ether. After 1 h of dropping, the mixture was stirred for 1 h, slowly cooled to 25 C, filtered and dried to give163g of pale white solidRate of 76.5%.HPLC purity 98%.

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, 106614-28-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou Keyao Pharmaceutical Technology Co., Ltd.; Zhou Junming; (10 pag.)CN107089981; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

13831-03-3, 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. 13831-03-3, name is tert-Butyl propiolate, This compound has unique chemical properties. The synthetic route is as follows.

To ethyl cyanoformate (10 g, 101.01 mmol) was added NH2OH-HCl (8.4 g, 121.74 mmol), K2CO3 (19.9 g, 144.20 mmol), and CH2C12/H2O (100 mL). The resulting mixture was stirred for 12 hr at room temperature. The solids were filtered out and the filtrated was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 6 g (45%) of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate as a white solid. To a mixture of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate (1 g, 7.58 mmol) and tert-butyl propiolate (940 mg, 7.46 mmol) was added Et3N (765 mg, 7.57 mmol) and toluene (50 mL). The resulting solution was stirred at 140 0C for 1 min. The resulting mixture was washed with 50 mL of H2O and then was extracted with 3 x 50 mL of dichloromethane. The organic layers were combined and washed with 20 mL of brine, then dried over anhydrous sodium sulfate. Evaporated the solvents and the residue was purified onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 1.1 g (61%) of 5 -tert-butyl 2-ethyl lH-imidazole-2, 5-dicarboxylate as a yellow solid.

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; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 18595-18-1

Example 1 A Preparation of 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(dimethylcarbamoyl)-1H- indazol-3-yl)cyclohex-3-enecarboxylic acid (1A) Step 1: Preparation of methyl 1H-indazole-6-carboxylate (A-2). Methyl 3-amino-4-methylbenzoate (A-l) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added drop-wise to the solution of starting material under ice-cooling at room temperature. The ice bath was removed and the mixture was stirred overnight. The half of the solvents were evaporated, the mixture was diluted with water (80 mL) and extracted with EtOAc(3×30 mL). The collected organic phase was washed with water and brine (2×200 mL), dried and evaporated to afford 2 (4.4 g), yield 83%. LCMS (ESI): calc’d for C9H8N202, [M+H]+: 177, found: 177.

The synthetic route of 18595-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26328; (2014); 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. 82911-71-5, name is (9H-Fluoren-9-yl)methyl 1H-benzo[d][1,2,3]triazol-1-yl carbonate, A new synthetic method of this compound is introduced below., 82911-71-5

4-[Bis(tert-butyl)phosphonomethyl]-N-Fmoc-DL-phenylalanine (Compound No. 4) A solution of amine compound No. 3 (770 mg, 1.93 mmol) in dioxane (10 mL) is stirred at room temperature 20 min) with aqueous 1 N NaOH (10 mL, 10 mmol, 5 equiv.). Carbon dioxide is then bubbled in (resulting pH 8.0-8.5) and Fmoc-OBT (857 mg. 2.40 mmol, 1.2 equiv) is added as a suspension in dioxane (3*10 mL) and stirred overnight at ambient temperature. The reaction mixture is partitioned between cold aqueous 5% citric acid (200 mL) and CHCl3 (3*100 mL); the combined organic is washed with cold 5% citric acid (1*100 mL); brine (1*200 mL); dried (MgSO4) and taken to dryness, yielding a light yellow resin (1.92g). The resin is taken up in CHCl3 and filtered through a silica pad. Unreacted Fmoc-OBT and faster impurities are removed with CHCl3 (5*100 mL) with product then being eluted (8*100 mL) with 1% EtOH in CHCl3 and taken to dryness, providing a foam (953 mg) which is dissolved in Et2 O (5 mL) and cooled with petroleum ether (20 mL) to yield compound No. 4 as a white powder: 835 mg (73%); mp 65-70 C. (gas, dec.).

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; The United States of America as represented by the Secretary of the Department of Health and Human Services; US5264607; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 25597-16-4, 25597-16-4

The resulting product (0.50, 2.6mmol) from step 5, ethyl 4,4,4-trifluorocrotonate (1.7g, 10.1mmol) and anhydrous potassium carbonate (0.36g, 5.6mmol) were dissolved in DMF (20mL), and then the system was stirred for 2hrs at 90C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.50g of the product (50%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.65(s, 1H), 7.16 (s, 1H), 7.07(s, 1H), 5.73(m, 1H), 4.30(m, 2H),1.27(m,3H)

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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; ZHANG, Yanmei; TALLEY, John Jeffrey; OBUKOWICZ, Mark G.; TU, Zhengchao; TORTORELLA, Micky; WANG, Yican; LIU, Jianqi; CHEN, Yan; LIU, Xiaorong; LU, Xin; EP2845854; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

40800-65-5, A common compound: 40800-65-5, name is Ethyl 4-amino-3-methylbenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of ethyl 4-amino-3-methylbenzoate (7.43 g)in DMF ..(35 ml) were added DMAP (506 mg) and acetic anhydride(4.66 g) at ambient temperature. After stirring for 4 hours,the reaction mixture was diluted with water (40 ml) andextracted with EtOAc (4 x 60 ml). The combined organicextracts were washed with saturated NaHCOs (2 x 30 ml) andbrine (3 x 100 ml) . The organic layer was dried over MgSC>4 andfiltered. Evaporation gave a residue which was triturated withEtOAc – n-hexane to give ethyl 4-(acetylamino)-3-methylbenzoate(4.324 g) as white crystals. The filtrate was evaporated andtriturated with EtOAc – n-hexane to give second crop (1.64 g).NMR(DMSO-d6,8) :. 1.31 (3H, t, J = 7.1Hz), 2.11 (3H, s) , 2.28(3H, s), 4.29 (2H, q, J = 7.1 Hz), 7.7-7.8 (3H, m), 9.37 (1H,br s) .MS: 244 (M+Na). .

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, Ethyl 4-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAICEL CHEMICAL INDUSTRIES, LTD.; WO2004/108686; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 140-39-6, name is p-Tolyl Acetate, molecular formula is C9H10O2, 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. 140-39-6.

NBS (13.91 g, 0.12 mol, 0.9 eq) and AIBN (2.17 g, 0.01 mol,0.1 eq) were placed in a Schlenk flask and put under an argonatmosphere. CHCI3was added followed by p-toy acetate (19.67 g, 0.13 mol). The mixture was refluxed for 4 h. After cooling down the volume of the mixture was reduced on rotavap to approximately a third and the suspension was filtered. 200 mL of CHCI3was added to the filtrate and it was 3x washed with 80 mL of water, the combined organic layers were dried with MgSC>4, filtered and volatiles were removed on rotavap. 5 mL of AcOEt was added, the mixture was shortly sonicated and while stirring, 40 mL of hexane was added causing precipitation. The mixture was put to a freezer overnight and then filtered washing the white solid with 25 mL of hexane giving 12.05 g (41 %, 0.05 mol) of the product. It was stored in the freezer. The NMR spectrum was in accordance with the literature (J. Org. Chem. 1981, 46 (15), 3029-3035)

The synthetic route of p-Tolyl Acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE JOHNS HOPKINS UNIVERSITY; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR V.V.I.; SLUSHER, Barbara; RAIS, Rana; VAVRA, Jan; TICHY, Toma?; MAJER, Pavel; JANCARIK, Andrej; TENORA, Luka?; (148 pag.)WO2018/94334; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics