Category: esters-buliding-blocks

Some common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, molecular formula is C7H11FO4, 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. HPLC of Formula: C7H11FO4

(0076) Into a solution, prepared at room temperature, of 7 g of potassium hydrogencarbonate in 70 g of a 30% aqueous formaldehyde solution were metered, after addition of 7.0 g of ethanol, 100 g of diethyl 2-fluoromalonate at an internal temperature of 20 to 25 C. within 1 hour. After stirring at room temperature for a further 3 hours, 122 g of product were obtained in a purity of about 84% by extraction with ethyl acetate and concentration of the extract in the form of a pale beige oil. For further purification, the product was recrystallized from toluene.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 685-88-1, its application will become more common.

Reference:
Patent; SALTIGO GMBH; VON DEM BRUCH, Karsten; SCHERWITZKI, Andreas; (8 pag.)US2017/197905; (2017); A1;,
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21961-31-9, name is Methyl 3-amino-5-chlorobenzoate, 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. HPLC of Formula: C8H8ClNO2

To a stirred solution of 3-amino-5-chloro-benzoic acid methyl ester (CAS 21961-31-9, 0.55 g) and pyridine (0.478 ml) in CH2C12 (14.8 ml) was added slowly a solution of chlorobutyrylchloride (0.372 ml) in CH2C12 (1.5 ml) at 0 C. The cooling bath was removed and the mixture was warmed to r.t. The mixture was diluted with diethyl ether and washed with 1 M HC1 and with water. The organic phase was dried (MgSC^), filtered, concentrated and dried under high vacuum to give 3-chloro-5-(4-chloro-butyrylamino)-benzoic acid methyl ester as a light brown solid. MS 290.0 ([M+H]+)

The synthetic route of 21961-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2006/27135; (2006); A1;,
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Related Products of 87-13-8, 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. 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The quinolone derivatives 1 were prepared by treating the appropriate aniline (100 mmol) with diethyl ethoxymethylenemalonate (100 mmol) under reflux in ethanol (5 mL) for 2-10 h to obtain the enamine derivatives that were then cyclized in refluxing diphenyl ether for 30 min-6 h [29]. These quinolones (13 mmol) were refluxed in thionyl chloride (20 mL), for 17 h, affording the corresponding chloro-derivatives 2a-g [22]. Reaction of 2a-g (4 mmol) with 2-hydrazinobenzothiazole (8 mmol) in toluene (30 mL), for 3 h, followed by a 2 h reflux in acetic acid gave the corresponding 2-(benzo[d]thiazol-2-yl)-8-substituted-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones 3a-g as solids which were collected by filtration under vacuum, washed with water and subsequent purified by washing with hot ethyl alcohol.

The synthetic route of Diethyl 2-(ethoxymethylene)malonate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reis, Raisa Da R.; Azevedo, Elisa C.; De Souza, Maria Cecilia B.V.; Ferreira, Vitor Francisco; Montenegro, Raquel C.; Araujo, Ana Jersia; Pessoa, Claudia; Costa-Lotufo, Leticia V.; De Moraes, Manoel O.; Filho, Jose D.B.M.; De Souza, Alessandra M.T.; De Carvalho, Natasha C.; Castro, Helena C.; Rodrigues, Carlos R.; Vasconcelos, Thatyana R.A.; European Journal of Medicinal Chemistry; vol. 46; 4; (2011); p. 1448 – 1452;,
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Reference of 18583-89-6, 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. 18583-89-6, name is Methyl 3-amino-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

PREPARATION 28 2-Methyl-3-methylamino benzoic acid To a solution of 500 mg (2.5 mmol) of 2-methyl-3-amino benzoate methyl ester in 5 mL of dimethylformamide, was added 387 mg (2.7 mmol) of methyl iodide and 700 mg (5.4 mmol) of diisopropylethylamine. The resultant reaction mixture was heated to 70° C. for approximately two hours and then poured into 10 mL of 1N potassium hydroxide. After about sixteen hours, the mixture was acidified to pH 6 by the addition of 2N hydrochloric acid. The desired titled compound was extracted into ethyl acetate, dried and reduced to dryness under reduced pressure to provide 343 mg of a white solid (m.p. 165°-167° C.). Yield: 84percent. 1 H NMR (CDCl3): delta12.52 (br. s, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.25 (t, J=7.9 Hz, 1H), 6.93 (d, J=7.8 Hz, 1H), 2.92 (s, 3H), 2.21 (s, 3H). Analysis for C9 H11 NO2: Calcd: C, 65.44; H, 6.71; N, 8.48; Found: C, 65.62; H, 6.84; N, 8.26.

The synthetic route of Methyl 3-amino-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US5484926; (1996); A;,
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Reference of 99548-55-7, These common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, 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.

REFERENCE EXAMPLE 2; Methyl 4-bromo-2-(bromomethyl)benzoate; To a solution of methyl 4-bromo-2-methylbenzoate (9.60 g, 0.42 mol, obtained in reference example 1) in CCI4 (150 mL), Lambda/-bromosuccinimide (7.46g, 0.42mol) and benzoyl peroxide (0.19g, 0.79mmol) were added. The reaction mixture was stirred 4h at room temperature while irradiated with a 250 Watt lamp and it was then filtered to remove the precipitated solids. The filtrate was washed with 1 N NaOH and water and it was dried over Na2SO4. The solvent was evaporated to afford 11.87 g of the desired compound as an oil that solidified on standing (yield: 92%, uncorrected).1H NMR (300 MHz, CDCI3) delta (TMS): 3.94 (s, 3 H), 4.90 (s, 2 H), 7.51 (dd, J = 8.4 Hz, J’ = 2.1 Hz, 1 H), 7.63 (d, J = 1.8 Hz, 1 H), 7.84 (d, J = 8.4 Hz, 1 H).

The synthetic route of 99548-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2007/337; (2007); A1;,
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Synthetic Route of 3196-15-4, 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.

[1074] Step 4: methyl 2-(6-(hydroxymethyl)-2-((4-methylbenzoyl)imino)benzo[d]thiazol-3(2H)-yl)butanoate[1075] To a solution of N-(6-(hydroxymethyl)benzo[d]thiazol-2(3H)-ylidene)-4-methylbenzamide (500 mg, 1.676 mmol) prepared in Step 3 in N,N-dimethylformamide (10 mL) were added potassium carbonate (695 mg, 5.028 mmol) and methyl 2-bromobutyrate (289 uL, 2.514 mmol). The reaction mixture was stirred at 50 ? overnight. .The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and then evaporated. Isopropyl ether was added to the resulting residue and then filtered. The resulting solid was dried under reduced pressure to give 470 mg of the titled compound as a white solid (Yield: 70%).[1076] 1H NMR (CDCl3, 400 MHz); 8.19 (d, 2H), 7.76 (s, 1H), 7.44 (d, 1H), 7.26 (m, 3H), 5.60 (brs, 1H), 4.79 (s, 2H), 3.65 (s, 3H), 2.51 (m, 2H), 2.42 (s, 3H), 1.97 (s, 1H), 1.57 (s, 2H), 0.89 (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; WO2013/43001; (2013); 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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 2,2,2-trifluoroacetate

According to the procedure for 5d, 4-bromo-1-(pentan-3-yl)-1H-pyrazole (1.23 g, 5.68 mmol) was dissolvedin dry THF (15 mL) at -78 C under nitrogen and was stirred for 10 min. n-BuLi (2.5 M inhexanes, 2.38 mL, 5.96 mmol) was added drop wise to the solution was stirred for 2 hours at -78 C. After two hours, methyl trifluoroacetate (0.68 mL, 6.81 mmol) was added drop wise andstirred for 30 min at -78 C. The solution was then allowed to warm up to room temperature andlet stir for overnight. The mixture was then quenched with NH4Cl (20 mL) and extracted withether (50 mL), and dried over MgSO4. After concentration in vacuo (note: remove shortly afterthe ether is removed, because the compound is quite volatile), the residue was purified with flash chromatography over silica gel (DCM: hexane = 20:80) to yield the product as a liquid in 67%yield (0.90 g).

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; Camerino, Eugene; Wong, Dawn M.; Tong, Fan; Koerber, Florian; Gross, Aaron D.; Islam, Rafique; Viayna, Elisabet; Mutunga, James M.; Li, Jianyong; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4405 – 4411;,
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Related Products of 889858-12-2,Some common heterocyclic compound, 889858-12-2, name is tert-Butyl 4-bromo-2-fluorobenzoate, molecular formula is C11H12BrFO2, 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 250 mL round-bottom flask was added (1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6- dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptane 52i (40 mg, 0.11 mmol, 1.00 equiv.), tert-butyl 4-bromobenzoate (40 mg, 0.16 mmol, 1.50 equiv.), Pd2(dba)3 (20 mg, 0.02 mmol, 0.20 equiv.), BINAP (26 mg, 0.04 mmol, 0.40 equiv.), Cs2CO3 (138 mg, 0.42 mmol, 4.00 equiv.), and toluene (5 mL). The resulting mixture was heated at 110°C overnight. After cooling to room temperature, the mixture was diluted with H2O (50 mL), and extracted with ethyl acetate (100 mL x 2). The combined organic extracts were washed with brine (100 mL x 2), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography eluting with ethyl acetate/hexane (1 :2) to afford tert-butyl 4- [(1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2- azabicyclo[2.2.1]heptan-2-yl]benzoate 52j (50 mg, 85percent) as a yellow oil.

The synthetic route of 889858-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 454-31-9, name is Ethyl 2,2-difluoroacetate, 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 454-31-9, Product Details of 454-31-9

Step 2: Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione. Ethyl difluoroacetate (4.06 g, 32.7 mmol) was dissolved in methyl t-butyl ether (50 mL). To the stirred solution was added 25 weight % sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected and washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.

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Reference:
Patent; G.D. Searle & Co.; US5990148; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 10601-80-6,Some common heterocyclic compound, 10601-80-6, name is Ethyl 3,3-diethoxypropionate, molecular formula is C9H18O4, 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: 2-aminopyridine 1a (47 mg, 0.5 mmol), ethyl 3,3-diethoxypropanoate 2 (285 mg, 1.5 mmol) and p-TsOH (8.6 mg, 10 mol %) were stirred in 2 mL of toluene for 6 h at 80 C. After completion of the reaction (monitored by TLC), the water (10 mL) was added. The aqueous solution was extracted with ethyl acetate (3×8 mL) and the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether/ethyl acetate = 2:1) to give a pure sample of 3a (Yellow crystal, 100 mg, 82%).

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

Reference:
Article; Liu, Wenjie; Wang, Shaohua; Zhan, Haiying; Li, Mingshan; Synlett; vol. 25; 10; (2014); p. 1478 – 1481;,
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Ester – an overview | ScienceDirect Topics