Category: 63920-73-0

Electric Literature of 63920-73-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 63920-73-0 name is 2-Amino-4,6-dimethoxybenzamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 2-hydroxymethyl-benzofuran-5-carbaldehyde (0.450 g, 2.55 mmol) and 2-amino-4,6-dimethoxybenzamide (0.500 g, 2.55 mmol) in N,N-dimethylacetamide (5 mL) were added sodium hydrogen sulfite (58.5%; 0.510 g, 2.80 mmol) and p-toluenesulfonic acid (50 mg, 0.25 mmol). The reaction mixture was stirred at 120 C. for 6 hours under nitrogen and cooled to room temperature. The separated solid was filtered, washed with ether (30 mL), water (30 mL), and ethyl acetate (20 mL), and then dried under vacuum to give the title compound as a yellow solid. Yield: 0.572 g (64%). 1H NMR (400 MHz, DMSO-d6): delta 12.07 (br s, 1H), 8.44 (d, J=2.0 Hz, 1H), 8.10 (dd, J=8.8 and 1.6 Hz, 1H), 7.67 (d, J=8.8 Hz, 1H), 6.89 (s, 1H), 6.76 (d, J=2.4 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 4.61 (s, 2H), 3.90 (s, 3H), 3.86 (s, 3H). MS (ES+) m/z: 353.20 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,6-dimethoxybenzamide, and friends who are interested can also refer to it.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281398; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 63920-73-0

This product was used in next step without further purification. To a solution of 2-dimethylaminomethyl-1H-indole-5-carbaldehyde (0.88 g crude, 4.35 mmol) and 2-amino-4,6-dimethoxy-benzamide (0.85 g, 4.35 mmol) in N,N-dimethylacetamide (15 mL) were added sodium hydrogen sulfite (58.5 wt %, 0.95 g, 5.22 mmol) and p-toluenesulfonic acid (0.99 g, 5.22 mmol). The reaction mixture was stirred at 120 C. for 5 hours under nitrogen, then cooled to room temperature, and concentrated under reduced pressure. 30% aqueous sodium carbonate (50 mL) was then added. The separated solid was filtered, washed with water (50 mL), and dried under vacuum. Crude compound was purified by the Simpliflash system (0-5% methanol in CH2Cl2 and 7 N ammonia in methanol 5% in CH2Cl2 as eluent) to give the title compound as an off-white solid. Yield: 0.83 g (50%). MP 187-188 C. 1H NMR (400 MHz, DMSO-d6): delta 11.82 (s, 1H), 11.34 (s, 1H), 8.38 (s, 1H), 7.93 (d, J=8.59 Hz, 1H), 7.40 (d, J=8.59 Hz, 1H), 6.73 (s, 1H), 6.49 (s, 1H), 6.40 (s, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 3.57 (s, 2H), 2.21 (s, 6H)

According to the analysis of related databases, 63920-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 63920-73-0, 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 63920-73-0 as follows.

A mixture of 2-amino-4,6-dimethoxy-benzamide (0.71 g, 3.71 mmol), 3,5-dimethyl-4-benzyloxy benzaldehyde (0.94 g, 3.90 mmol), sodium hydrogensulfite (0.68 g, 3.90 mmol) and p-toluenesulfonic acid (70 mg, 0.37 mmol) in N,N-dimethylacetamide (25 mL) was stirred at 150 C. for 16 h. The reaction mixture was cooled to room temperature and diluted with water (200 mL). The resulting solid was collected by filtration and washed with hexanes to afford 2-(4-benzyloxy-3,5-dimethyl-phenyl)-5,7-dimethoxy-3H-quinazolin-4-one as a white solid (1.2 g, 79%).

According to the analysis of related databases, 63920-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter Ronald; US2013/281397; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, belongs to amides-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 63920-73-0, Product Details of 63920-73-0

Example 26. Preparation of 2-[4-(5,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]-N-(4-methoxy-phenyl)-acetamide [0257] To a solution of 4-hydroxy-3,5-dimethyl-benzaldehyde (9.00 g, 60.0 mmol) in ethanol (300 mL) were added potassium carbonate (24.9 g, 180 mmol) and methyl bromoacetate (11.4 mL, 120 mmol). The reaction mixture was stirred at 95C under nitrogen for 16 hours. The mixture was concentrated to dryness under reduced pressure. Water (150 mL) and 1 N NaOH solution (90 mL) were added to the residue. The mixture was stirred at room temperature for 30 minutes, then washed with ether. Concentrated HCI was added slowly to the aqueous solution until a large amount of white precipitate formed. The solid was filtered, washed with water, and air-dried, to give (4-formyl-2,6-dimethyl-phenoxy)- acetic acid as a white solid. Yield: 11.1 g (89%).[0258] To a solution of (4-formyl-2,6-dimethyl-phenoxy)-acetic acid (3.12 g, 15.0 mmol) and 2-amino-4,6-dimethoxy-benzamide (2.94 g, 15.0 mmol) in N,N-dimethylacetamide (50 mL) were added sodium hydrogen sulfite (58.5 wt%, 3.02 g, 16.5 mmol) and p-toluenesulfonic acid monohydrate (0.285 g, 1.50 mmol). The reaction mixture was stirred at 1200C for 17 hours under nitrogen and cooled to room temperature. The precipitate was filtered, washed with water, then methanol, and air-dried to give 1.29 g [4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid. The filtrate was concentrated to dryness and water was added. The suspension was stirred for 30 minutes and filtered. The solid was washed with water, then methanol. After air drying, 3.78 g more [4-(5,7-dimethoxy-4-oxo-3, 4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]- acetic acid was obtained. Yield: 5.07 g (88%).[0259] To a mixture of [4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid (0.400 g, 1.04 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI; 0.240 g, 1.24 mmol), 1-hydroxybenzotriazole hydrate (HOBt; 0.17 g, 1.24 mmol) in DMF (10 ml_) was added 4-methylmorpholine (0.20 mL, 1.8 mmol). After 10 minutes, p-anisidine (0.26 g, 2.08 mmol) was added. The mixture was stirred at room temperature under nitrogen for 2.5 days. The solvent was removed under reduced pressure. Water was added, stirred for 30 minutes. The solid was filtered, washed with water, and dried in air. The crude product was purified by column chromatography (silica gel, 230-400 mesh; 5% MeOH in CH2CI2 as eluent). The product fractions were combined, concentrated to dryness. The solid was dissolved in small amount of dichloromethane, precipitate out by adding ether. The precipitate was filtered, washed with ether, dried under vacuum to afford the title compound as a white solid. Yield: 0.26 g (51%). 1H NMR (400 MHz, CDCI3): delta 10.30 (br s, 1 H), 8.52 (s, 1 H), 7.83 (s, 2H), 7.58 (dd, J = 6.8 and 2.0 Hz, 2H), 6.93 (dd, J = 6.8 and 2.0 Hz, 2H), 6.84 (d, J = 2.4 Hz, 1 H), 6.48 (d, J = 2.0 Hz, 1 H), 4.44 (s, 2H), 3.97 (s, 3H), 3.94 (s, 3H), 3.83 (s, 3H), 2.42 (s, 3H). MS (ES+) m/z: 490.55 (M+1).

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; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 63920-73-0,Some common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, 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 28. Preparation of 2-[4-(4-hydroxy-butoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one [0261] To a solution of 4-hydroxy-3,5-dimethyl benzaldehyde (5.00 g, 33.3 mmol) in DMF (30 ml_) were added 4-bromo butan-1-ol (6.11 g, 39.9 mmol) and CS2CO3 (16.24 g, 50.0 mmol). The reaction mixture was stirred at room temperature for 48 hours. Water was added and the products were extracted with ethyl acetate (2 * 200 ml_). The combined organic phase was washed with water (100 ml_), brine (100 ml_), and dried over anhydrous Na2SO4. Solvent was removed and the crude compound was purified using the Simpliflash system (40% ethyl acetate in hexane as eluent) to give 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde as a colorless liquid. Yield: 0.66 g (7%).[0262] To a solution of 2-amino-4,6-dimethoxy-benzamide (0.50 g, 2.53 mmol) and 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde (0.66 g, 2.53 mmol) in N,N-dimethyl acetamide (10 ml_), NaHSO3 (0.50 g, 2.79 mmol) and p-TSA (96 mg, 0.50 mmol) were added and the reaction mixture was heated at 115C for 16 hours, then cooled to room temperature. Solvent was removed under reduced pressure. Water (100 ml_) was added and the mixture was stirred for 1 hour. The solid separated was filtered and dried. The solid was again washed with diethyl ether to give the title compound as a white solid. Yield: 1.69 g (82%). 1H NMR (400 MHz, CDCI3): delta 9.10 (s, 1H), 7.66 (s, 2H), 6.83 (d, J = 2.4 Hz, 1 H), 6.46 (d, J = 2.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.85 (t, J = 6.0 Hz, 2H), 3.78 (m, 2H), 2.36 (s, 6H), 1.94 (m, 2H), 1.85 (m, 2H). MS (ES) m/z: 399.12 (M+1) (100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,6-dimethoxybenzamide, its application will become more common.

Reference:
Patent; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, belongs to amides-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. Computed Properties of C9H12N2O3

4-bromo-ethyl – benzoic acid ethyl ester (4.0g, 16.46mmol) was added in THF (30mL) solution of N- ethylpiperazine (3.76g,32.92mmol), The reaction mixture was stirred at room temperature for 16 hour. The reaction mixture was diluted withwater and the product was extracted with ethyl acetate. The combined organiclayers were washed with water, brine, Na 2SO 4dry. The solvent was removed togive 4.61g of crude 4- (4-ethyl-piperazin-1-yl-methyl) – benzoic acid ethylester (100% yield). The LAH (0.792g, 20.86mmol)was added to a dry 3-necked flask, THF (60mL) under cooling. Was slowly added under cooling 4- (4-ethyl-piperazin-1-yl-methyl) – benzoic acid ethyl ester(4.61g, 16.69mmol) in THF (10mL) was added. After the addition was complete,the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled to 0 deg.]C, was added 10% NaOH solution, then water was added. The organic layer wasseparated, the aqueous layer was extracted with ethyl acetate. The combinedorganic layers were washed with water, brine, Na 2SO 4dry. The solvent wasremoved to give 2.78gof crude (4- (4-ethyl-piperazin-1-yl-methyl) phenyl) -methanol, 78% yield.anhydrous CH2Cl2 cooled to -78 deg.] C containingthe (100 mL) 3-necked flask was added oxalyl chloride(1.8g, 14.25mmol) and DMSO (1.85g, 23.76mmol),at -78 deg.] C and the mixture was stirred for 15 minutes. It was added at -78 (4- (4- ethyl-piperazin-1-yl-methyl) phenyl) – methanol(2.78g, 11.88mmol) in CH2Cl 2The (10 mL) was stirred at -78 1 hour. Was then added at -78 Et 3N (4.8g,47.52mmol). The reaction mixture was brought to room temperature. Water was added, the organiclayer was separated. The aqueous layer was extracted with CH 2Cl 2extraction.The combined organic layers were washed with water, brine, Na 2SO 4dry. Then, the solvent was removedto give crude 4- (4-ethyl-piperazin-1-yl-methyl)benzaldehyde (2.5g, 91%). 2-amino-4,6-dimethoxy – benzamide (150mg, 0.76mmol) and 4-(4-ethyl-piperazin-1-yl-methyl) benzaldehyde (177mg, 0.76mmol) in N , N- dimethylacetamide(10 mL) was added NaHSO 3(150mg,0.84mmol) and p-TSA (319mg, 1.68mmol), thereaction mixture was at 150 was heated for 5 hours. The reactionmixture was cooled to room temperature, water was added, the mixture was treated with NaHCO 3neutralize. The solventwas removed under reduced pressure to give the crude product, which waspurified by column chromatography to give 2- (4 -((4-ethyl-piperazin-1-yl) methyl) phenyl) -5,7 dimethoxy – quinazolin -4 (3H) -one (87mg, 27%), converted to the hydrochloride salt. Selected data: MS(ES) m / z: 409.11; MP278-280 (decomposition

The synthetic route of 63920-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP; HANSEN, H; (62 pag.)CN103319408; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 63920-73-0, 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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-picolinaldehyde (13.10 g, 32.46 mmol) and 2-amino-4,6-dimethoxybenzamide (6.68 g, 34.08 mmol) in N,N-dimethylacetamide (150 ml) was added NaHSO3 (8.90 g, 48.69 mmol) and p-toluenesulfonic acid monohydrate (6.17 g, 32.46 mmol). The reaction mixture was stirred at 120 C. for 14 h. After that time the reaction was cooled to rt, concentrated under reduced pressure, diluted with saturated Na2CO3 (150 mL) and the precipitated solids were collected by filtration, washed with water and dried under vacuum. The product was washed with diethyl ether and dried to give 2-(5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (17.38 g, 92%) as light yellow solid: ESI MS m/z 580 [M+H]+.

The synthetic route of 2-Amino-4,6-dimethoxybenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; Fairfax, David John; Martin, Gregory Scott; Quinn, John Frederick; Duffy, Bryan Cordell; Wagner, Gregory Steven; Young, Peter Ronald; US2014/140956; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 63920-73-0, A common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, 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 20. Preparation of 2-[4-(2-hydroxy-ethoxy)-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one [0239] To a flask (250 mL) with a magnetic stirrer were added 4-hydroxybenzalde (10.0 g, 81.8 mmol), 2-chloroethanol (26.3 g, 327 mmol), potassium carbonate (22.6 g, 163 mmol), and ethanol (80 mL). The reaction mixture was stirred at 700C for 16 hours. Potassium carbonate was filtered and ethanol was removed. The residue was diluted with ethyl acetate (200 ml_) and washed with 5% sodium hydroxide (100 ml_), water (100 ml_), and brine (100 ml_). The crude product was purified by column chromatography (silica gel, 230-400 mesh), using hexane / ethyl acetate (1 :1) as eluent, to afford 4-(2-hydroxy-ethoxy)-benzaldehyde. Yield: 10.0 g (73%).[0240] To a solution of 2-amino-4,6-dimethoxy-benzamide (0.400 g, 2.00 mmol) and 4-(2-hydroxy-ethoxy)-benzaldehyde (0.340 g, 2.00 mmol) in N, N- dimethylacetamide (8 ml_) were added NaHSO3 (0.390 g, 2.20 mmol) and p-TSA (38 mg, 0.20 mmol). The reaction mixture was stirred at 115-1200C for 5 hours and cooled to room temperature. The solvent was removed under reduced pressure. The residue was diluted with water (40 ml_) and the solid was collected, mixed with methanol (50 ml_), and stirred for 30 min. The solid was filtered and rinsed with ether (30 ml_) to give the title compound as white solid. Yield: 0.42 g (61%). 1H NMR (400 Hz, DMSO-d6): delta 11.98 (s, 1H), 8.18 (d, 2H), 7.08 (d, 2H), 6.78 (s, 1 H), 6.52 (s, 1H), 4.98 (s, 1 H), 4.10 (t, 2H), 3.90 (s, 3H), 3.84 (s, 3H)1 3.74 (t, 2H). MS (ES+) m/z: 343.13 (M+1).

The synthetic route of 63920-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 63920-73-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 63920-73-0 name is 2-Amino-4,6-dimethoxybenzamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 2-hydroxymethyl-benzofuran-5-carbaldehyde (0.450 g, 2.55 mmol) and 2-amino-4,6-dimethoxybenzamide (0.500 g, 2.55 mmol) in N,N-dimethylacetamide (5 mL) were added sodium hydrogen sulfite (58.5%; 0.510 g, 2.80 mmol) and p-toluenesulfonic acid (50 mg, 0.25 mmol). The reaction mixture was stirred at 120 C. for 6 hours under nitrogen and cooled to room temperature. The separated solid was filtered, washed with ether (30 mL), water (30 mL), and ethyl acetate (20 mL), and then dried under vacuum to give the title compound as a yellow solid. Yield: 0.572 g (64%). 1H NMR (400 MHz, DMSO-d6): delta 12.07 (br s, 1H), 8.44 (d, J=2.0 Hz, 1H), 8.10 (dd, J=8.8 and 1.6 Hz, 1H), 7.67 (d, J=8.8 Hz, 1H), 6.89 (s, 1H), 6.76 (d, J=2.4 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 4.61 (s, 2H), 3.90 (s, 3H), 3.86 (s, 3H). MS (ES+) m/z: 353.20 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,6-dimethoxybenzamide, and friends who are interested can also refer to it.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281398; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics