Month: November 2020

541-16-2, 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 541-16-2 as follows.

2) Preparation of 2-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one After 55% sodium hydride (322 mg, 7.38 mmol) was added to a solution of di-tert-butyl malonate (970 mg, 4.48 mmol) in N,N-dimethylformamide (10 mL), 4-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphen yl)-2H-pyridazin-3-one (1.8 g, 4.90 mmol) was added under ice-cold stirring. The reaction mixture was stirred at room temperature for 1 hour, poured into water, and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was isolated and purified by chromatography on silica gel (hexane/ethyl acetate=3/1) to yield the title compound as a yellow powder (yield: 1.39 mg, 61.8%). 1H NMR (400 MHz, CDCl3) delta: 0.44-0.50 (2H, m), 0.50-0.58 (2H, m), 1.41 (18H, s), 1.56 (1H, m), 3.12 (2H, d, J=7.8 Hz), 3.87 (1H, t, J=7.8 Hz), 3.94 (3H, s), 4.09 (2H, d, J=7.8 Hz), 7.01 (1H, dd, J=8.5, 8.5 Hz), 7.43 (1H, d, J=8.5 Hz), 7.50 (1H, s), 7.57 (1H, dd, J=12.4, 2.2 Hz).

According to the analysis of related databases, Di-tert-Butyl malonate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOWA CO., LTD.; US2004/2497; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 5026-62-0, name is Sodium 4-(methoxycarbonyl)phenolate, 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 5026-62-0. 5026-62-0

EXAMPLE 60 1,4-Bis(1,3-benzodioxol-5-yloxy)-2-methyl-2-butene 3.2 g (0.02 mol) of sodium salt of 3,4-methylendioxyphenol are suspended in 60 cc of 1,2-dimethoxyethane and cooled to 0-5. 2.28 g (0.01 mol) of 1,4-dibromo-2-methyl-2-butene, dissolved in 20 cc of 1,2-dimethoxyethane are added while stirring. The mixture is stirred at 20-25 during the course of 20 hours and at 50 during the course of 5 hours; it is subsequently filtered and the filtrate is evaporated. The residue is taken up in ether, extracted with saturated salt solution, the ether phase is dried with sodium sulphate and evaporated. The obtained viscous oil is purified by chromatography on silica gel with hexane/ethyl acetate 5: 1 and subsequently by crystallization from ethyl acetate/hexane. M.P. 73.5-74. In analogous manner as described in Example 60, but using sodium salt of 4-hydroxy-benzoic methyl ester in the place of the sodium salt of 3,4-methylendioxy-phenol, the following compound is produced.

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 Sodium 4-(methoxycarbonyl)phenolate.

Reference:
Patent; Sandoz Ltd.; US3978134; (1976); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

37466-90-3, These common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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.

Synthesis of 2-Oxo-2,3-dihydro-lH-benzoimidazole-5-carboxylic acid ethyl ester ’22a): 3,4-Diamino-benzoic acid ethyl ester (100 mg, 0.56 mmol) was dissolved in 5 mL of IHF and cooled to 00C. Triethyamine (77 muL, 0.56 mmol) was added followed by potassium carbonate (230 mg, 1.68 mmol). Triphosgene (82 mg, 0.28 mmol) was added in one portion, md the reaction mixture was then warmed up to room temperature and quenched with saturated ammonium chloride solution. The mixture was extracted with ethyl acetate. The organic layers were combined, washed with brine and dried over MgSO4. Solvent was then removed and the residue was purified by column chromatography (60% ethyl acetate/hexanes). The product (92 mg, 80%) was obtained as a white solid. MS (ES) M+H expected = 207.1, found = 207.1.

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 37466-90-3.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2007/51062; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

455-75-4, A common compound: 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, 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 3-amiotano-4-fluorobenzoate (547 g, 30 mmol) and pyridine (2 55 mL, 33 mmol) in DCM (150 mL) was added 2,6-diotafluorobenzenesulfonyl chloride (4 45 mL, 33 mmol) The reaction was stirred overnight at rt After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7 87 g (66% yield) of the product of Step A as a white powder ES-LCMS m/z 360 (M+H)

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

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-14-7, 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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 4-amino-3-methyl-benzoate (12.17 g, 73.70 mmol) in DCM (135 mL) was added 1-pyridin-1-ium-1-yliodanuidylpyridin-1-ium (Boron Tetrafluoride Ion) (30.14 g, 81.00 mmol). The reaction mixture was stirred for 1.5h, then 1-pyridin-1-ium-1- yliodanuidylpyridin-1-ium (Boron Tetrafluoride Ion) (2.740 g, 7.367 mmol) was added and the mixture was stirred for another 2h, then quenched with aqueous saturated NaHCO3 (100 mL).The layers were separated. The aqueous layer was extracted with DCM (2 x 100 mL). The combined organic extracts were washed with aqueous 1M Na2S2O3 (100 mL) and dried over Na2SO4, filtered and concentrated. The crude residue was co-evaporated with heptane (2x) and purified by flash chromatography on a BiotageTM snap 340g silica cartridge, using a gradient of EtOAc (0-25%) in Hex as eluent. The fractions were combined and concentrated to provide thetitle compound (18.0 g, 84% yield). ?H NMR (400 MHz, CDC13) oe 8.23 (s, 1H), 7.71 (s, 1H),4.51 (s, 2H), 3.85 (s, 3H), 2.25 (s, 3H).

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; VERTEX PHARMACEUTICALS INCORPORATED; GALLANT, Michel; TRUCHON, Jean-Francois; REDDY, Thumkunta, Jagadeeswar; DIETRICH, Evelyne; VAILLANCOURT, Louis; VALLEE, Frederic; (131 pag.)WO2016/199105; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2555-28-4, 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. 2555-28-4, name is 7-Methoxy-4-methylcoumarin belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A general procedure for preparation of compounds 5, 9a-b and13: the corresponding N-bromosuccinimide (1.2 equiv) was addedslowly to a solution of 7-methoxycoumarin (1 equiv) and sodiumacetate (0.05 equiv) in DMF, and the mixture was stirred at 75 Cfor 6 h. After pouring into brine, and washing, then mixture wasextracted with ethyl acetate. The combined organic layers werewashed with brine, dried over anhydrous Na2SO4 and then filteredand concentrated in vacuum. The product was purified by columnchromatography (0-20% ethyl acetate in petroleum ether).

The synthetic route of 7-Methoxy-4-methylcoumarin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Lu; Hu, Zhiye; Luo, Junjie; Tang, Chu; Zhang, Silong; Ning, Wentao; Dong, Chune; Huang, Jian; Liu, Xianjun; Zhou, Hai-Bing; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3531 – 3539;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

51329-15-8, name is Methyl 3,5-dibromobenzoate, 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. 51329-15-8

A mixture of compound 2 (5.6 g, 19.2 mmol), PMBSH (3.8 g, 24.7 mmol), Pd2(dba)3 (1.7 g, 1.9 mmol), Xantphos (2.2 g, 3.8 mmol) and DIPEA (4.9 g, 38.0 mmol) in 1,4-dioxane (100 mL) was heated to 100 C. for 16 h. The reaction mixture was concentrated under vacuum, and purified by column chromatography to give the compound 3 (3.9 g, 56%).

Statistics shows that 51329-15-8 is playing an increasingly important role. we look forward to future research findings about Methyl 3,5-dibromobenzoate.

Reference:
Patent; Novira Therapeutics, Inc.; Hartman, George D.; US2015/225355; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, name is Ethyl 3-bromobenzoate, 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. 24398-88-7

Step 1 : Ethyl 3-(3-methoxypropyl)benzoateTo a THF solution (0.1 M) of allyl methyl ether (1.4 eq.) was added, at 0 0C, 9- borabicyclo[3.3.1]nonane (2.4 eq.) over a period of 30 min. The solution was stirred at 0 0C for 1 h and then warmed slowly to RT over 16 h. To the resulting clear solution was then added sodium methoxide (2.4 eq.), Cl2Pd(dppf)-dichloromethane complex (5% loading) and ethyl 3-bromobenzoate (1 eq.). The now brown suspension was heated to reflux for 16 h. The reaction mixture was cooled to RT, quenched with sat. aq. NH4Cl and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex -^ 4: 1 (v/v) Hex : EtOAc) afforded the title compound as a light yellow oil.

Statistics shows that 24398-88-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 3-bromobenzoate.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2007/9250; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

35180-01-9, These common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, 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.

Preparation of Compound 165Compound 165. A 20 mL microwave vial was charged with starting acid (300 mg, 0.632 mmol), potassium carbonate (1 14 mg, 0.822 mmol), sodium iodide (66.3 mg, 18.1 mu, 0.442 mmol), DMF (10 mL) and chloromethyl isopropyl carbonate (116 mg, 0.758 mmol). Heated at 80 C in microwave for 20 min, then the reaction mixture was partitioned between EtOAc and water (80 mL each). The organic layer was separated, washed with water then brine (80 mL each), dried (magnesium sulfate), filtered and concentrated. The resulting residue was purified by MPLC using an Isco Combiflash (40 g column) 0-80% EtOAc in hexanes linear gradient over 24 column volumes at 40 mL/min. Product isolated from column was dissolved in MeCN (10 mL), treated with water (8 mL) then the resulting mixture was frozen and lyophilized. Gave 166 (291 mg, 0.479 mmol, 76%) as a white solid. Analysis carried out by LCMS (60-98% aqueous MeCN, formic acid modifier, 7 min, C4) ESI-MS m/z calc. 590.2662, found 591.59 (M+l)+; Retention time: 2.59 minutes. 1H NMR (300.0 MHz, DMSO) delta 7.27 (s, 1H), 5.84 (dd, J = 6.2, 9.7 Hz, 2H), 4.91 (d, J = 16.7 Hz, 1H), 4.80 (septet, J = 6.2 Hz, 1H), 3.89 (d, J = 16.7 Hz, 1H), 3.55 (br s, 4H), 3.45 – 3.35 (m, 4H), 2.13 – 1.98 (m, 1H), 1.79 – 1.33 (m, 7H), 1.30 (s, 9H), 1.24 (d, J = 6.2 Hz, 6H), 0.77 (d, J = 6.4 Hz, 3H) and 0.75 – 0.57 (m, 2H) ppm.

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 35180-01-9.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; GREEN, Jeremy; WILSON, Dean, M.; KONG, Laval, Chan Chun; DAS, Sanjoy, Kumar; POISSON, Carl; COURT, John, J.; TANG, Qing; LI, Pan; COLLIER, Philip, N.; WAAL, Nathan; LAUFFER, David, J.; DORSCH, Warren; WO2012/6055; (2012); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

816-27-3, 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of ethyl 2-ethoxy-2-iminoacetate (2.5 g, 17.22 mmol, 1.0 eq) and H4C1 (738 mg, 13.78 mmol, 0.8 eq) in EtOH (60 mL) was stirred at rt overnight. The reaction solution was filtered. The filtrate was concentrated and the residue was washed with acetone. The resulting residue was dried in vacuo to afford ethyl 2-amino-2- iminoacetate (1.8 g, 69%) as a white solid. IH NMR (DMSO-d6, 300 MHz): delta 9.76 (br, 4 H), 4.35 (q, 2 H), 1.31 (t, 3 H).

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; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics