Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, 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 60792-79-2, Quality Control of 2,2′-Oxybis(ethylamine) dihydrochloride

A suspension of 0.2 M 2,2′-oxydiethylamine dihydrochloride (0.135 gm, 0.74 mmole) and 0.4 M DIEA (0.32 ml, 1.85 mmole) in 2.5 DMF was added to 4-morpholino-1,8-naphthalic anhydride (0.068 gm, 0.24 mmole) and heated at 150 C with microwave treatment under nitrogen for 12 minutes. The mixture was cooled, diluted with dichloromethane, washed with sat. NaHCO3, dried over MgSO4, and concentrated under vacuum to give N-aminoethylethoxy-4-morpholino-1,8 naphthalimide 9. 1H NMR (300 MHz, CDCl3): delta 8.59 (IH, d, J = 7.2 Hz); 8.53 (IH, d, J = 7.8 Hz); 8.42 (IH, d, J = 8.4 Hz); 7.70 (IH, t, J= 7.2 Hz); 7.25 (d, IH, J= 8.1 Hz); 4.43 (2H, t, J= 5.8 Hz); 4.02 (4H, m); 3.80 (2H, t, J= 6.0 Hz); 3.54 (2H, t, J = 5.2 Hz); 3.26 (4H, m); 2.81 (2H, t, ./ = 5.7 Hz).

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, 2,2′-Oxybis(ethylamine) dihydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; WO2006/60533; (2006); A2;,
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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. 107622-80-0, name is (4-Phenoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Production example 3 0.88 g of a BOP reagent and 0.40 g of triethylamine were successively added to a mixture of 0.28 g of 2-aminonicotinic acid, 0.40 g of 4-phenoxybenzylamine and 10 ml of DMF. The obtained mixture was stirred at a room temperature for 4 hours. Thereafter, ice and a saline solution were successively added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was further washed with a saline solution 3 times, and it was then dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. 0.80 g of the obtained residue was subjected to silica gel column chromatography, so as to obtain 0.62 g of N-(4-phenoxyphenyl)methyl-2-aminonicotinic acid amide (hereinafter referred to as the present compound 3).The present compound 3 [Show Image] 1H-NMR (DMSO-D6) delta: 4.42 (2H, d, J = 5.9 Hz), 6.59 (1H, dd, J = 7.8, 4.9 Hz), 6.97-6.99 (4H, m), 7.08 (2H, br), 7.10-7.13 (1H, m), 7.32-7.40 (4H, m), 7.95 (1H, dd, J = 7.8, 1.7 Hz), 8.08 (1H, dd, J = 4.9, 1.7 Hz), 8.98 (1H, t, J = 5.9 Hz).

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; Sumitomo Chemical Company, Limited; EP2248423; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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 20781-20-8, COA of Formula: C9H13NO2

To a solution of ethyl (4aS)- 1 -(4-fluorophenyl)-6-oxo-4,5 ,7,8-tetrahydrobenzo [fjindazole-4a- carboxylate (ig) (3.16 g, 8.92 mmol) and (2,4-dimethoxyphenyl)methanamine (2.68 mL, 17.83 mmol) in DCE (40 mL) was added acetic acid (1.54 mL, 26.75 mmol). After the reaction was stirred at rt for 5 mm and cooled down in an ice-bath, sodium triacetoxyborohydride (5.lg, 24.08 mmol) was added in portions. 5 Minute later, the reaction solution was allowed to warm to rt and continued stirring for 30 mm. The solution was quenched (sat. aq. NaHCO3) and extracted (EtOAc). The organic layers were washed (brine), dried (Na2SO4) and concentrated under reduced pressure. The cmde product was purified by silica gel chromatography (Si02, 0%-75 % EtOAc/hexanes, gradient elution) to provide the title compound (lila) (4.15 g, 92% yield) as an off-white solid. mlz (ESI, +ve ion) = 506.3 [M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2,4-Dimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; REW, Yosup; SUN, Daqing; YE, Qiuping; ZHOU, Haiying; KAWAI, Hiroyuki; MOORE, Jared; PHAM, Johnny; WU, Kejia; ZHU, Liusheng; YAMASHITA, Dennis; (288 pag.)WO2018/191283; (2018); A1;,
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Some common heterocyclic compound, 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, molecular formula is C9H13NO, 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. Application In Synthesis of 2-(Benzyloxy)-1-ethanamine

A solution of N,N-diisopropylethylamine (2.31 ml, 13.2 mmol) and intermediate 29 (0.79 mg, 2.2 mmol) in dry tetrahydrofuran (6.6 ml) (+ few drop of Nu,Nu-dimethylformamide) was added drop wise to a solution of 1 ,1 ‘-carbonyl diimdazole (0.61 g, 3.74 mmol) in dry tetrahydrofuran (6 ml). The mixture was stirred at room temperature for 1 hour and 2-benzyloxyethanamine (0.998 g, 6.6 mmol) was added. The mixture was stirred at room temperature. When the reaction is completed, ethyl acetate was added and the organic layer was washed with water. The organic layer was dried, filtered and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography over silica gel using dichloromethane and methanol as eluents. The product fractions were collected and the solvent was evaporated.Yield: 1.065 g of intermediate 30 (90%)LCMS method 1 : MH+ = 537, RT = 1.035 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38336-04-8, its application will become more common.

Reference:
Patent; IPSEN PHARMA S.A.S.; ONCODESIGN S.A.; HOFLACK, Jan; BLOM, Petra; WO2013/46029; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-08-4, name is 3-(Difluoromethoxy)aniline, 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 22236-08-4, HPLC of Formula: C7H7F2NO

EXAMPLE 2 Preparation of 2,3-dichloro-N-(m-difluoromethoxyphenyl)maleimide 16.7 g (0.1 mole) of 2,3-dichloromaleic anhydride is dissolved in 100 ml of dioxane, and a solution of 15.9 g (0.1 mole) of m-difluoromethoxyaniline in 30 ml of dioxane is added dropwise to it at room temperature over 20 minutes with stirring. Thereafter, the resulting solution is stirred at 70-80 C. for 2 hours and the dioxane is then distilled off under a reduced pressure. Water is added to the residue to precipitate crystals. The precipitated crystals are filtered off and recrystallized to give 29.2 g (yield: 95%) of 2,3-dichloro-N-(m-difluoromethoxyphenyl)maleimide melting at 122-124 C. in the form of light yellow plate crystals.

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; Showa Denko Kabushiki Kaisha; US4455315; (1984); A;,
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Application of 19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Bromo-3-methoxyaniline (380 mg, 1.88 mmol), 2-(2-chlorophenylamino)-2-methylpropanoic acid (482 mg, 2.26 mmol) and diisopropylethylamine (413 mg, 558 jil, 3.2 mmol) were combined with dimethylformamide (15 ml). 0- (7 -Azabenzotriazol- 1 -yl)-N,N,N? ?N? – tetramethyluronium hexafluorophosphate (HATU, 1.22 g, 3.2 mmol) was added. The reaction mixture was stirred at room temperature oyernight. Reaction mixture was poured on water andextracted with dichloromethane. Chromatography (silicagel, ethyl acetate / heptane = 20:80 to50:50) yielded N-(4-bromo-3-methoxyphenyl)-2- (2-chlorophenylamino)-2-methylpropanamide (457 mg, 61percent) as brown solid. MS: mle =399.3 [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, 4-Bromo-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CECCARELLI, Simona M.; JAGASIA, Ravi; JAKOB-ROETNE, Roland; PETERS, Jens-Uwe; WICHMANN, Juergen; WO2014/79850; (2014); A1;,
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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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