Month: June 2021

Reference of 24988-36-1, 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. 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 14 is combined with anhydrous tetrahydrofuran:dioxane (5:0.9), and the mixture is agitated under a nitrogen atmosphere until a homogeneous solution is achieved. The solution is cooled to -3 C and 1.3 eq. of /-PrMgCl-LiCl in tetrahydrofuran is added. The reaction mixture is agitated at 0 C until the formation of the mono-Grignard is complete as determined by HPLC analysis. Next, a solution of 1.1 eq. of 3-chloro-2-fluorobenzaldehyde in tetrahydrofuran is added. This mixture is allowed to stir at 0 0C until the formation of Compound 15a is complete by HPLC. Next, additional /-PrMgCl-LiCl solution in tetrahydrofuran (2.5 eq.) is added and the reaction mixture is warmed to about 20 C. After conversion to the second Grignard intermediate is complete, the reaction mixture is cooled to 3 C. Anhydrous CO2 (g) is charged to the reaction mixture at about 5 0C. The reaction mixture is adjusted to about 20 C. After the carboxylation reaction is complete by HPLC, the reaction mixture is cooled to about 10 C and water is charged to quench the reaction followed by the addition of concentrated hydrochloric acid to adjust the pH to no more than 3. The reaction mixture is then warmed to about 20 C. The phases are separated. The organic phase is solvent exchanged to a mixture of isopropyl alcohol and water and the resulting slurry is cooled to about 0 0C. The product is isolated by filtration, washed with a mixture of isopropyl alcohol and water and dried at about 40 C to yield Compound 3.

The synthetic route of 1,5-Dibromo-2,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2009/36161; (2009); A1;,
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Related Products of 4003-89-8, A common heterocyclic compound, 4003-89-8, name is 7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine, molecular formula is C11H15NO, 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.

Example 17; Acetic acid 2-[3-(7-methoxy-1 ,2,3,4-tetrahydro-naphthalen-2-yl)-thioureido]-ethyl ester(compound 17); A solution of 7-methoxy-1 ,2,3,4-tetrahydro-naphthalen-2-ylamine (0.34 g) in toluene (10 mL) was treated with acetic acid 2-isothiocyanato-ethyl ester (0.28 g, cf. Collect. Czech. Chem Commun. 1986, 51 , 112-117), refluxed for 1 h and stirred at room temperature overnight. Purification by chromatography on silica gel yielded the product (0.45 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:
Patent; BASF SE; WO2008/145615; (2008); A2;,
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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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 162705-07-9

General procedure: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

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 162705-07-9.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
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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. 4316-51-2, name is 4-Methoxytriphenylamine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C19H17NO

To a 250 mL four-necked flask was added a solution of 4-methoxytriphenylamine in DMF (previously prepared from 5.5 g of 4-methoxytriphenylamine dissolved in 75 mL of DMF), protected by nitrogen and magnetically stirred and cooled to 0 C. ,Using a constant pressure dropping funnel, 12.24g of POCl3 was slowly added dropwise to the reaction solution. After the addition was completed, the reaction conditions were maintained for 1h. Heating to 80 reaction.After the reaction was completed, the reaction mixture was poured into ice water and quenched, extracted with methylene chloride, washed with deionized water five times and anhydrous sulfurThe mixture was dried over magnesium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was separated by column chromatography (petroleum ether / ethyl acetate = 10/1, v / v)Pure, to obtain a green oily liquid, the yield was 94.8%.

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 4316-51-2.

Reference:
Patent; Hebei University of Science and Technology; Lv Haijun; Zhou Haoran; Jin Gengen; Yu Yifeng; Ma Weiqing; Kang Caihong; Wang Lili; (37 pag.)CN107298689; (2017); A;,
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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 50592-87-5 as follows. Computed Properties of C7H15BrO

(3) Production of 4′-methoxyhexyloxy-biphenyl-4-carboxylic acid. 8.4 Grams of 1-bromo-6-methoxyhexane and 4.5 g of 4′-hydroxybiphenyl-4-carboxylic acid were refluxed in 100 ml of water and 400 ml of ethanol for 4 hours. Concentrated hydrochloric acid was added to the reaction mixture so that the mixture showed pH 1, then 150 ml of water was added, and the resultant mixture was refluxed for 1 hour. The reaction mixture was cooled to precipitate a crystal, and the crystal was recovered by filtration. The so-obtained crystal was recrystallized from acetone. Yield 55%.

According to the analysis of related databases, 50592-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; US5340498; (1994); A;,
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Electric Literature of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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: A microwave vial (2?5mL) was charged with 1 equiv of mon-subtituted triazine in acetonitrile. Then 1.1 equiv of DIPEA and 1 equiv of aryl amine derivative were added. The vial was sealed and heated under microwave irradiated between 10 and 180 min at 150°C. After completion of the reaction (monotored by TLC), the solvent was removed by vacuum evaporation. The resultant mixture was dissolved in EtOAc or CH2Cl2, a solution of 2N HCl was added then water. The layer organic was extracted whit EtOAc or CH2Cl2 and dried with MgSO4, The product was purified by silica gel chromatography or recrisallized in ethanol 95.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tber, Zahira; Wartenberg, Mylene; Jacques, Jean-Eddy; Roy, Vincent; Lecaille, Fabien; Warszycki, Dawid; Bojarski, Andrzej J.; Lalmanach, Gilles; Agrofoglio, Luigi A.; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4310 – 4319;,
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Electric Literature of 64465-53-8, 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 64465-53-8 as follows.

1 ,1 -Dimethylethyl 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-1 – piperidinecarboxylate (D9)A solution of 1 ,1-dimethylethyl 4-oxo-1 -piperidinecarboxylate (1.41g, 7.1mmol) and 4-fluoro-3-methoxyaniline (1g, 7.1mmol) was stirred at room temperature for 1h. Sodium tri(acetoxy)borohydride (1.95g, 9.2mmol) was then added and stirring continued over-weekend. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution, dried and then concentrated in vacuo. Column chromatography eluting with 0-50% Et2C7petroleum ether gave the title compound as a white solid (1.45g). deltaH (CDCI3, 400MHz) 6.89 (1 H1 dd), 6.22 (1 H, dd), 6.09 (1H1 m), 4.03 (2H, br s), 3.84 (3H, s), 3.36 (1 H, br s), 2.92 (2H, m), 2.03 (2H, m), 1.46 (9H, s), 1.32 (2H, m).

According to the analysis of related databases, 64465-53-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/144400; (2007); 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. 867288-00-4, name is 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine

A solution of 123 L of a 10% aqueous solution of Na2C03, 1.5 L of a 25 wt. % aqueous solution of ammonia and 2.0 kg of a filtration resin (Dicalite) were charged to the reactor and the mixture stirred for 5 minutes. The mixture was recirculated through a filter until clarification of the liquors (35 min) and charged into a reactor. 60 L of isopropyl acetate were added and the mixture was stirred for 10 minutes and the phases (A1 +01 ) were allowed to separate. The aqueous phase (A1 ) was transferred to a different reactor and 60 L of isopropyl acetate were charged. The mixture was stirred and the phases (A2 + 02) were allowed to separate. Both organic phases (01+02) were charged into a reactor and 108 L of a 10 wt. % aqueous solution of Na2C03 were added. The mixture was stirred and the phases (A3+03) were allowed to separate. The organic phase (03) was stirred with 108 L of a 10 wt. % aqueous solution of Na2C03 and the phases (A4+04) were allowed to separate. The organic phase (04) was stirred with 100 L demineralised water and the phases (A5+05) were allowed to separate. The organic phase (05) was filtered over a filtration resin (Dicalite) in a filter and charged in to a reactor. 2.2. Distillation: The organic phase (05) was distilled during 2 hours under reduced pressure (approx. 750 mm Hg) keeping the distilled mixture at temperature below 65 C.

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; ALMIRALL, S.A.; BOIX BERNARDINI, Maria, Carmen; WO2011/45059; (2011); A1;,
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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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

A solution of [2-(trifluoromethyl)phenyl]acetic acid (3.06 g, 15.0 mmol) in toluene (30 mL) was heated to 80C, 1,1-di-tert-butoxy-N,N-dimethylmethaneamine (14.4 g, 60.0 mmol) was added and the mixture was stirred at 80C for 2 hr. After cooling to room temperature, the solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The obtained extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100 – 30/70) to give tert-butyl [2-(trifluoromethyl)phenyl]acetate (3.16 g, 81%). To a solution of tert-butyl [2-(trifluoromethyl)phenyl]acetate (3.10 g, 11.9 mmol) in DMF (36 mL) was added sodium hydride (60% oil, 524 mg, 13.1 mmol), and the mixture was stirred at room temperature for 30 min. 1-Chloro-3-iodopropane (1.34 mL, 12.5 mmol) was added, and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100 – 30/70) to give tert-butyl 5-chloro-2-[2-(trifluoromethyl)phenyl]pentanoate (3.63 g, 91%). A solution of tert-butyl 5-chloro-2-[2-(trifluoromethyl)phenyl]pentanoate (3.56 g, 9.83 mmol) in TFA (10 mL) was stirred at room temperature for 18 hr. The solvent was evaporated under reduced pressure, ethyl acetate was added, and the mixture was extracted with 1 M aqueous sodium hydroxide solution. The extract was acidified with 6 M hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil (2.74 g, 99%). 1H NMR (CDCl3) delta: 1.55 – 1.75 (1 H, m), 1.76 – 2.04 (2 H, m), 2.16 – 2.34 (1 H, m), 3.50 (2 H, t, J=6.3 Hz), 4.06 (1 H, t, J=7.3 Hz), 7.31 – 7.45 (1 H, m), 7.46 – 7.62 (2 H, m), 7.67 (1 H, d, J=7.7 Hz).

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2455380; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36865-41-5, name is 1-Bromo-3-methoxypropane, belongs to ethers-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 36865-41-5, Recommanded Product: 1-Bromo-3-methoxypropane

Step 2: N’-Isopropylidene-N-(3-methoxypropyl)-hydrazinecarboxylic acid tert-butyl ester To a solution of hydrazinecarboxylic acid tert-butyl ester (4.67 g, 27.16 mmol) in toluene (90 mL) was added pulverized potassium hydroxide (1.98 g, 35.3 mmol) and tetrabutylammonium hydrogensulfate (904 mg, 2.72 mmol). The solution was heated to 50 C. in a preheated oil bath and 1-bromo-3-methoxypropane (3.67 mL, 32.6 mmol) was added drop-wise over 45 minutes. The solution was then heated to 80 C. for 3 h. The solution was cooled to room temperature and washed with water (3*150 mL) until the water layer was neutral. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to provide N’-isopropylidene-N-(3-methoxypropyl)-hydrazinecarboxylic acid tert-butyl ester as a viscous oil (6.49 g, 98%), which was used without further purification. Mass spectrum: m/z: 245.4 (M+1).

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, 1-Bromo-3-methoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anderson, Kevin William; Fotouhi, Nader; Gillespie, Paul; Goodnow, Robert Alan; Guertin, Kevin Richard; Haynes, Nancy-Ellen; Myers, Michael Paul; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Rossman, Pamela Loreen; Scott, Nathan Robert; Thakkar, Kshitij Chhabilbhai; Tilley, Jefferson Wright; Zhang, Qiang; US2007/225280; (2007); A1;,
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