40872-87-5 Archives - Esters-buliding-blocks

27-Sep News The important role of 40872-87-5

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Application of 40872-87-5,Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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 250 mL round bottom flask equipped with a stir bar was added 2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid (4.0 g, 17.0 mmol) (from Example 24 supra), 3-amino-4-chloro-benzoic acid methyl ester (4.6 g, 25.0 mmol), N,N-dimethylformamide (45 mL) and triethylamine (4.9 mL, 35.0 mmol), after which HATU (9.5 g, 25.0 mmol) was added all at once. The reaction was allowed to stir at room temperature for 18 hours after which the reaction was diluted with ethyl acetate and the precipitate was filtered, rinsed with water, ethyl acetate and then dried under high vacuum to provide 4-chloro-3-[(2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)-amino]-benzoic acid methyl ester as an off-white solid. (Yield 5.27 g, 76%).

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The important role of 40872-87-5

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Related Products of 40872-87-5, These common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, 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.

It heated and dried at 120 degrees C under decompression of a p-toluenesulfonic-acid monohydrate (25.6g) for 1 hour. The methyl 3-amino-4-chlorobenzoate (10g) and the propiononitrile (20 ml) were added there, and it heated at reflux for 16 hours. After cooling a reaction mixture radiationally, the saturated sodium bicarbonate aqueous solution (250 ml) was added, and it stirred for 10 minutes. Ethyl acetate extracted, after carrying out decompression distilling off of the propiononitrile (50mlx3). The organic layer was dried and concentrated in vacuum with anhydrous sodium sulfate. Silica gel column chromatography (developing solvent: petroleum ether/ethyl acetate) refined the obtained residue, and it obtained the mark compound (8.5g).

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; IKEDA, JUNYA; NAKAMURA, TAKANORI; OTAKA, HIROMICHI; (133 pag.)JP2016/28016; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Simple exploration of Methyl 3-amino-4-chlorobenzoate

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

Synthetic Route of 40872-87-5, The chemical industry reduces the impact on the environment during synthesis 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, I believe this compound will play a more active role in future production and life.

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Continuously updated synthesis method about C8H8ClNO2

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Related Products of 40872-87-5, A common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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.

7-Oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid (0.275 g, 1.44 mmol) and methyl 3-amino-4-chlorobenzoate (401 mg, 2.16 mmol) was suspended in DMF (4.5 mL). Triethylamine (728 mg, 7.19 mmol) was added, resulting in a clear, pale yellow solution. HATU (821 mg, 2.16 mmol) was then added. Solid began to precipitate out of solution again after 30 minutes. After stirring at room temperature for 6 hours the thick mixture was diluted with EtOAc. The solid was collected and dried to give methyl 4-chloro-3-(7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)benzoate. (Yield 0.295 g, 822 mumol, 57.2%).

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

New learning discoveries about C8H8ClNO2

Electric Literature of 40872-87-5, The chemical industry reduces the impact on the environment during synthesis 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, I believe this compound will play a more active role in future production and life.

Methyl 4-chloro-3-cyanobenzoate (2). To a solution of methyl 3-amino-4- chlorobenzoate (15.0 g, 81.0 mmol) in H20/conc. HC1 (150 mL/17 mL), nitrous acid solution (5.6 g, 81 mmol) was added drop-wise at 0C and stirred for 30 min. The reaction mixture was neutralized with sodium hydroxide solution. The resulting diazonium salt solution was added to a solution of cuprous chloride (8.0 g, 81.0 mmol) and sodium cyanide (10.7 g, 218.0 mmol) at 0 C and stirred at room temperature for 4h. The reaction mixture was quenched with water (150 mL) and extracted with ethyl acetate (200 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude obtained was triturated with diethyl ether and n-pentane to yield 2 (8.0 g, 51%) as a white solid. 1H NMR (400 MHz, CDCI3) delta 3.88 (s, 3H), 4.26 (brs, 2H), 7.29 (d, J = 8.2 Hz, 1H), 7.34-7.37 (dd, J =1.9, 8.2 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H)

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Simple exploration of Methyl 3-amino-4-chlorobenzoate

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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

2-Methoxy-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid (131 mg, 557 mumol) was suspended in DMF (1.70 mL). Methyl 3-amino-4-chlorobenzoate (155 mg, 835 mumol) was added, followed by triethylamine (283 mg, 390 muL, 2.8 mmol). HATU (318 mg, 835 mumol) was then added. Solution was initially clear but solid soon began to precipitate out of solution. After stirring at room temperature for 16 hours the reaction mixture was diluted with EtOAc (1 mL). The solid was then collected by filtration, washed with EtOAc and dried to give methyl 4-chloro-3-(2-methoxy-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)-benzoate. (Yield 108 mg, 244 mumol, 43.8%).

According to the analysis of related databases, 40872-87-5, the application of this compound in the production field has become more and more popular.

Extracurricular laboratory: Synthetic route of Methyl 3-amino-4-chlorobenzoate

Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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. category: esters-buliding-blocks

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40872-87-5, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

New learning discoveries about 40872-87-5

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 40872-87-5 as follows. Product Details of 40872-87-5

Triethylamine (1.16 g, 11.5 mmol) was added to a mixture of 7-methoxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carboxylic acid (from Example 15 supra) (2.3 g, 10.45 mmol) and HATU (4.37 g, 11.5 mmol) in dry DMF (30 mL). The resulting mixture was stirred at room temperature until clear solution was obtained. 3-Amino-4-chloro-benzoic acid methyl ester (2.32 g, 12.55 mmol) was added and the resulting mixture was stirred for another 20 hours. The reaction mixture was diluted with water (300 mL), aqueous saturated NaHCO3 (60 mL) and ethyl acetate (150 mL). After thorough mixing, off white precipitate was collected by filtration, washed water, ethyl acetate and MeOH, and dried under reduced pressure to give 4-chloro-3-[(7-methoxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carbonyl)-amino]-benzoic acid methyl ester as an off-white solid. (Yield 2.9 g, 71.8%). 1H NMR (300 MHz, d6-DMSO) delta 12.42 (s, 1H), 9.18 (s, 1H), 9.01 (s, 1H), 8.91 (s, 1H), 7.70 (d, 2H, J=1.1 Hz), 6.61 (s, 1H), 3.95 (s, 3H), 3.89 (s, 3H). LC-MS: [M+H]+ 388.

According to the analysis of related databases, 40872-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The important role of 40872-87-5

Related Products of 40872-87-5,Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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.

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

The important role of C8H8ClNO2

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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 40872-87-5

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics