Category: 20781-20-8

Electric Literature of 20781-20-8, These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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.

To a solution of compound 58 (6.6 g, 33.5 mmol) in dichloromethane (100 mL)were added DIPEA (8.65 g, 67 mmol), HOBt (5.4 g, 36.85 mmol) and EDCI (9.6 g, 50.3mmol). After about 15 mm stirring, to the homogeneous reaction mixture was added asolution of 2,4-dimethoxybenzyl amine (5.6 g, 33.5 mmol) in dichloromethane (50 mL)dropwise under nitrogen atmosphere. The resulting mixture was stirred under nitrogenatmosphere at room temperature for 16h. The reaction mixture was washed successively with iN NaOH (100 mL), water (100 mL) and brine (100 mL). The organic phase was then dried over Na2SO4 and evaporated to give a crude solid product 59 that crystallized from ethyl ether. Filtration and open air suction drying afforded an off-white solid pureproduct 9.8g (96%), (MS: [M+1] = 347).

Statistics shows that (2,4-Dimethoxyphenyl)methanamine is playing an increasingly important role. we look forward to future research findings about 20781-20-8.

These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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. Safety of (2,4-Dimethoxyphenyl)methanamine

Ethyl 4,6-dichloronicotinate (60 g, 0.27 mmol) at room temperatureDimethyl sulfoxide (500 ml)To the solution was added 2,4-dimethoxybenzylamine (47.8 g, 0.287 mmol)And triethylamine (55 g, 0.545 mmol) and the reaction mixture was stirred at room temperature overnight.To the reaction was added water (2 L), extracted with ethyl acetate (2.5 L x 2), washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo,Ethyl 6-chloro-4- (2,4-dimethoxybenzylamino) nicotinate was obtained.The product was dissolved in trifluoroacetic acid (300 ml), and the reaction mixture was stirred with heating at 50 C overnight. The mixture was cooled to room temperature and concentrated to dryness. The mixture was extracted with ethyl acetate (2.5 liters x 2), washed with brine (500 ml), and then the organic phase was washed with saturated aqueous sodium bicarbonate solution (500 ml). The organic phase was dried and concentrated in vacuo. The obtained product was purified by silica gel column chromatography (petroleum / ethyl acetate = 2/1) to obtain ethyl 4-amino-6-chloronicotinate (34 g, yield 62.3%) as a white solid. .

The synthetic route of (2,4-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nuowosida Pharmaceutical Co., Ltd.; Li Bing; (67 pag.)CN110256432; (2019); A;,
Ether – Wikipedia,
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These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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. Safety of (2,4-Dimethoxyphenyl)methanamine

Ethyl 4,6-dichloronicotinate (60 g, 0.27 mmol) at room temperatureDimethyl sulfoxide (500 ml)To the solution was added 2,4-dimethoxybenzylamine (47.8 g, 0.287 mmol)And triethylamine (55 g, 0.545 mmol) and the reaction mixture was stirred at room temperature overnight.To the reaction was added water (2 L), extracted with ethyl acetate (2.5 L x 2), washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo,Ethyl 6-chloro-4- (2,4-dimethoxybenzylamino) nicotinate was obtained.The product was dissolved in trifluoroacetic acid (300 ml), and the reaction mixture was stirred with heating at 50 C overnight. The mixture was cooled to room temperature and concentrated to dryness. The mixture was extracted with ethyl acetate (2.5 liters x 2), washed with brine (500 ml), and then the organic phase was washed with saturated aqueous sodium bicarbonate solution (500 ml). The organic phase was dried and concentrated in vacuo. The obtained product was purified by silica gel column chromatography (petroleum / ethyl acetate = 2/1) to obtain ethyl 4-amino-6-chloronicotinate (34 g, yield 62.3%) as a white solid. .

The synthetic route of (2,4-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nuowosida Pharmaceutical Co., Ltd.; Li Bing; (67 pag.)CN110256432; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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, Safety of (2,4-Dimethoxyphenyl)methanamine

a. Potassium carbonate (2.97 g, 21.5 mmol) was added to a mixture of 2- chloropyrimidine (2.1 g, 17.9 mmol), 2,4-dimethoxybenzylamine (3.0 g, 17.9 mmol) and acetonitrile (20 mL). The reaction mixture was heated at reflux for 16 h, allowed to cool to ambient temperature and partitioned between ethyl acetate (150 mL) and water (10 mL). The organic phase was washed with water (2 10 mL) and brine (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was triturated in diethyl ether (20 mL), washed with hexanes (20 mL) and purified by column chromatography, eluting with a 0-100% gradient of ethyl acetate in hexanes to afford A/-(2,4-dimethoxybenzyl)pyrimidin-2-amine as a pale yellow solid in 84% yield (3.70 g): MS (ES+) m/z 245.9 (M + 1).

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; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Quality Control of (2,4-Dimethoxyphenyl)methanamine

Added to the Schlenk reaction tube 18.1 mg (0.10 mmol) copper acetate, 16.0 mg (0.025 mmol) three (2, 2′ – bipyridyl) ruthenous, 16.0 mg (0.02 mmol) tert lithium ethoxide, using Schlenk double-row tube vacuum pumping, access oxygen state, adding 79 uL (0.5 mmol) 2, 4 – dimethoxybenzylamine, 2.5 ml dimethyl sulfoxide, the use of the Schlenk tube with double row sustained and the oxygen to the reaction system, the temperature control of the reaction system 35 C, white light LED lamp (wavelength 400 – 760 nm) irradiation, stirring for 20 hours after the, adding 3 ml saturated sodium acid sulfite aqueous solution and 10 ml ethyl acetate, extraction liquid, anhydrous magnesium sulfate drying, to remove the magnesium sulfate, the resulting organic phase is concentrated, the concentrate with silica gel column chromatography, to obtain 2, 4 – dimethoxy carbonitrile, yield 90%

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUAIHAI INSTITUTE OF TECH; Huaihai Technology College; TAO CHUANZHOU; Tao Chuanzhou; WANG BIN; Wang Bin; SUN LEI; Sun Lei; LIU ZHOU; Liu Zhou; ZHAI YADONG; Zhai Yadong; (5 pag.)CN107814751; (2018); A;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H13NO2

To a solution of 5-fluoro-2-nitrobenzoic acid (6.6g, 35.66 mmol) in dichloromethane (100 mL) were added DIPEA (9.22 g, 71.3 mmol), HOBt (6.0 g, 39.2 mmol) and EDCI (10.2 g, 53.5 mmol). After about 15 min stirring, to the reaction mixture was added a solution of 2,4-dimethoxybenzyl amine (5.96 g, 35.66 mmol) in dichloromethane (50 mL) dropwise under nitrogen atmosphere. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 16 h. The reaction mixture was washed successively with 1N HC1 (100 mL), sat. NaHCCb (100 mL) and brine (100 mL). The organic phase was then dried over MgS04. Filtration and solvent removal in vacuo afforded a yellowish solid, wt: 9.3g (78%). MS: [M+l] = 335.

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 20781-20-8.

Reference:
Patent; AGENEBIO, INC.; MEKONNEN, Belew; BUTERA, John, A.; HUANG, Jianxing; PATEL, Hemantbhai; JIANG, Qin; HERR, Robert, Jason; MAYHEW, Nicholas, James; FREEMAN, Emily, Elizabeth; (682 pag.)WO2019/246300; (2019); A1;,
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Reference of 20781-20-8,Some common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

Step 1: N-(2-((tert-Butyldimethylsilyloxy)methyl)- l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5( lH)-ylidene)- 1 -(2,4-dimethoxyphenyl)methanamine To solution of 2-((tert-butyldimethylsilyloxy)methyl)-l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5(lH)-one (Intermediate 4, 7.458 g, 20.86 mmol) in CH2C12(65 mL) was added 2,4-dimethoxybenzylamine (3.30 mL, 21.97 mmol) and NEt3(7.80 mL, 55.96 mmol). The mixture was cooled to 0 C before TiCl4solution (1M CH2C12, 13.60 mL, 13.60 mmol) was added dropwise via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The mixture was diluted with CH2C12(150 mL) and then quenched with NaHC03(aq. satd., 50 mL). Upon vigorous shaking, the organic phase was separated with a PTFE phase separator and then dried over Na2S04. Removal of the solvent afforded the product (10.6 g, quant.) as yellow oil which was taken directly into next step without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2,4-Dimethoxyphenyl)methanamine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

Saturated NaHC03 (100 mL) was added to a solution of (2,4- dimethoxyphenyl)methanamine (10 mL, 66.4 mmol) in CH2CI2 (100 mL) and the mixture was stirred vigorously at 25 C for 15 min. Then thiophosgene (10 mL, 131 mmol) was added via syringe to the bottom layer. The mixture was stirred at 25 C for 1.5 h. The aqueous layer was separated and the organic layer was washed with brine (100 mL), dried over NaSC>4, filtered, and concentrated in vacuo to afford l-(isothiocyanatomethyl)-2,4-dimethoxy benzene. HNMR (400 MHz, CDCI3): delta 7.19 (d, J = 7.6 Hz, 1H), 6.47-6.50 (m, 2H), 4.61 (s, 2H), 3.84 (s, 3H), 3.82 (s, 3H).

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; KHAN, Tanweer, A.; CUMMING, Jared, N.; OLSEN, David, B.; BODDEY, Justin, A.; COWMAN, Alan, F.; SLEEBS, Brad, E.; (86 pag.)WO2017/142825; (2017); A2;,
Ether – Wikipedia,
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Synthetic Route of 20781-20-8, These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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.

Step 1: synthesis of methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate (86) A mixture of 2,4-dimethoxybenzylamine (58.7 mmol, 8.81 ml, 9.81 g), methyl 5-chloro-4-nitrothiophene-2-carboxylate (45.1 mmol, 10 g) and potassium carbonate (180 mmol, 24.94 g) were stirred at rt in Acetonitrile (226 mL) for 1 h. Reaction was quenched with water and the resulting precipitate was collected to give methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate 86 (15.5 g, 97%). NMR (400 MHz, CDCl3) 3.82 (s, 3H), 3.85 (s, 3H), 3.86 (s, 3H), 4.45 (d, J=5.9 Hz, 2H), 6.46 (dd, J=8.2 Hz and 2.3 Hz, 1H), 6.50 (d, J=2.3 Hz, 1H), 7.20 (d, J=8.2 Hz, 1H), 7.99 (s, 1H), 8.89 (br s, 1). (m/z)=353 (M+H)+.

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 20781-20-8

General procedure: Amine (1 mmol), 2-aminothiophenol (2 mmol), BODIPY photosensitizer (0.01 mmol, 1.0 mol%), and acetonitrile (5 mL) were added to a dry 10-mL flask. The flask was pressurized with air (2 bar) and then heated to 50 C. The solution was then irradiated using a 35-W xenon lamp through a cutoff filter (0.72M NaNO2 aqueous solution, which is transparent for light >385nm, because lamps could emit a small amount of ultraviolet light). After the reaction was completed, the solvent was evaporated under reduced pressure. The crude product was further purified using column chromatography.

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 20781-20-8.

Reference:
Article; Zhou, Zeyin; Yang, Weijun; Synthetic Communications; vol. 44; 21; (2014); p. 3189 – 3198;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem