Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 125568-73-2, name is Methyl 5-amino-2,4-difluorobenzoate, belongs to esters-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 125568-73-2, Quality Control of Methyl 5-amino-2,4-difluorobenzoate

A mixture of methyl 5-amino-2,4-difluoro-benzoate (2, 3.0 g, 0.016 mol) and 2-chloro-N-(2- chloroethyl)ethanamine hydrochloride (3.719 g, 0.021 mol) in diethylene glycol monomethyl ether (12 mL) was heated to 170C for 2.5h. Progress of the reaction was monitored by TLC. Water was added to the reaction mixture and extracted with ethyl acetate. The organic part was discarded. Then pH of the aqueous part was adjusted with sodium bicarbonate and extracted with ethyl acetate. Combined organic part was dried over anhydrous sodium sulphate, and concentrated under reduced pressure. The crude product obtained was purified by column chromatography to afford the product (1.5 g, 29.9%). LCMS (ESI positive ion) m/z: calculated: 256.25; Observed; 257.0 (M+l).

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; ITEOS THERAPEUTICS; CROSIGNANI, Stefano; GOMES, Bruno; HOUTHUYS, Erica; (216 pag.)WO2018/178338; (2018); A1;,
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Application of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, molecular formula is C7H13BrO2, 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 7.1 : (preparation of a compound of formula (XI)) 3-(2-Hydroxy-2-methylpropylamino)propionic acid tert-butyl ester 1 g of 1 -aminomethylpropan-2-ol (1 1 .22 mmol) is placed in 10 ml of DMF. 1 .58 ml of triethylamine (1 1 .22 mmol) and 1 .87 ml of tert-butyl 3-bromopropionate (1 1.22 mmol) prediluted in 5 ml of DMF are successively added dropwise. After stirring for 18 hours at room temperature, the solvent is evaporated off. The residue is chromatographed on silica gel with a gradient of from 0% to 20% MeOH in DCM to give 2 g of 3-(2-hydroxy-2- methylpropylamino)propionic acid tert-butyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-bromopropanoate, its application will become more common.

Reference:
Patent; SANOFI; BRAUN, Alain; CRESPIN, Olivier; FORICHER, Yann; MARCINIAK, Gilbert; MUZET, Nicolas; NICOLAI, Eric; PASCAL, Cecile; VIVET, Bertrand; VIVIANI, Fabrice; WO2013/111106; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, belongs to esters-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. SDS of cas: 26759-46-6

Example 1: (Production of 6,7-dimethoxyquinazolin-4-one); Using acetic acid and an inorganic base, ammonia, as a catalyst, 6,7-dimethoxyquinazolin-4-one was produced in the manner mentioned below. 0.84 g (4 mmol) of methyl 4,5-dimethoxyanthranilate, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.05 g (2.8 mmol) of ammonia from a pressure cylinder were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with methanol and then dried in vacuum at 70C for 2 hours to obtain 0.77 g of a crystal. The obtained crystal was analyzed for the purity by high-performance liquid chromatography, and its purity was 99.5 %; and 6,7-dimethoxyquinazolin-4-one was obtained at a yield of 93.0 %. The result is shown in Table 1. Examples 2 to 4, and Comparative Examples 1 and 2: (Production of 6,7-dimethoxyquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 1, for which, however, the catalyst was changed as in Table 2. In Example 4, ammonium acetate was used as the catalyst; and in Comparative Examples 1 and 2, formic acid or potassium carbonate, respectively, was used alone as the catalyst like in JP-A 2002-338550 (Patent Reference 4). From the results in Table 1, it is known that the reaction system with acetic acid and a base coexisting therein of the present invention gives 6,7-dimethoxyquinazolin-4-one at a higher yield than the conventional reaction system with formic acid or potassium carbonate alone therein.

The synthetic route of 26759-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; EP1997812; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, A new synthetic method of this compound is introduced below., SDS of cas: 581065-95-4

SI-6 (76 mg, 0.27 mmol, 1.2 eq.), COMU (115 mg, 0.27 mmol, 1.2 eq.), and N- methylmorpholine (74 pL, 0.67 mmol, 3 eq.) were dissolved in 333 pL of DMF and incubated for 1 min. Amino-PEG4-t-butyl ester (72 mg, 0.22 mmol, 1 eq.) was added in 667 pL and the reaction was stirred for lh at room temperature. The reaction was then diluted with ethyl acetate (10 mL) and water (10 mL). The organic layer was washed with water (3×1 OmL) and 1N HC1 (lxlOmL). The organic layer was collected, dried over anhydrous MgS04 and removed under reduced pressure. The residue was purified by flash chromatography (DCM:EtOAc, 1 : 1) to provide the title compound as a colorless oil (44 mg, 22%). ‘H NMR (500 MHz, Chloroform -r/) d 7.10 (s, 1H), 6.81 – 6.69 (m, 2H), 4.46 (d, J= 11.3 Hz, 2H), 4.18 (s, 1H), 3.83 – 3.72 (m, 2H), 3.70 – 3.67 (m, 4H), 3.63 (s, 8H), 3.61 – 3.57 (m, 6H), 3.54 (dd, J= 7.6, 3.2 Hz, 2H), 2.70 (s, 2H), 2.48 (td, J= 6.5, 1.5 Hz, 2H), 1.98 (d, J= 5.2 Hz, 2H), 1.43 (d, J= 3.1 Hz, 9H). HRMS (ESI) [M+H]+ for C28H44CIN2O9 587.2730, found 587.2721.

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; THE SCRIPPS RESEARCH INSTITUTE; ZHANG, Xiaoyu; CROWLEY, Vincent; CRAVATT, Benjamin; (121 pag.)WO2020/77278; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H6BrFO2

Step 1: To methyl 3-bromo-4-fluorobenzoate (3.02 g, 13.0 mmol) in ether (30 ml) at 0 C. add dropwise MeMgBr (3.0M in ether, 11 ml, 33 mmol). Stir 1 h and pour onto ice. Acidify with 1N HCl, separate the ether, wash with 1N NaHCO3, dry (MgSO4), and concentrate to obtain the product as a colorless oil

The synthetic route of 82702-31-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2004/220194; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 34529-06-1, name is Dimethyl 3-aminophthalate, A new synthetic method of this compound is introduced below., Product Details of 34529-06-1

3-Pentylamino-phthalic acid dimethyl ester To a stirred solution of 3-amino-phthalic acid dimethyl ester (3.14 g, 15 mmol) in methylene chloride (50 ml) under a nitrogen atmosphere were added valeraldehyde (2.0 ml, 18.75 mmol) and acetic acid (5.18 ml, 90 mmol). The mixture was stirred for 5 minutes followed by addition of sodium triacetoxyborohydride (6.36 g, 30 mmol). The reaction was stirred for 30 minutes, diluted with methylene chloride (50 ml), washed with water (2*100 ml), saturated aqueous sodium bicarbonate (2*100 ml), brine (100 ml), and dried (MgSO4). The solvent was evaporated in vacuo to give 4.19 g of product (100%) that used without further purification. 1H NMR (DMSO-d6) d 7.31 (t, J=7.9 Hz, 1H), 6.81-6.75 (m, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 3.15 (bs, 2H), 1.68-1.60 (m, 2H), 1.45-1.32 (m, 4H), 0.89 (t, J=6.9 Hz, 3H).

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; Robarge, Michael J.; Chen, Roger Shen-Chu; Muller, George W.; Man, Hon-Wah; US2003/96841; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 13671-00-6, The chemical industry reduces the impact on the environment during synthesis 13671-00-6, name is Methyl 2,6-difluorobenzoate, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of an appropriate methyl esters17(a-j) (1.0 mmol) in 50 mL of methanol was added 99 %hydrazine hydrate (4.0 mmol) and the mixture was refluxedfor 5 h up to reaction completed (TLC). After completionof reaction, it was allowed to cool and the obtained solidwas washed with methanol. The crude products wererecrystallized from ethanol.

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 2,6-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Murty; Penthala, Raju; Polepalli, Sowjanya; Jain; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 627 – 643;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 120-51-4 as follows. Computed Properties of C14H12O2

General procedure: A mixture of amine (6.0 mmol), ester (3.0 mmol) and Ru-MACHO (1% mol) in toluene (3.0 mL) was placed in a flask and replaced withnitrogen gas. Then, t-BuOK (20% mol) was added in the mixture in the nitrogen gas flowing. The mixture was heated by reflux under the nitrogen atmosphere. During this time, the nitrogen gas was passed through the Schlenk line allowing the hydrogen gas to evolve from the reaction to escape the reactor. After the 48 h, the solvent was evaporated and the crude product was purified by flash chromatography on silica-gel to give the desired amides in 55-98% yields. The structures of the obtained amide swere determined by FT-IR and 1HNMR.

According to the analysis of related databases, 120-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Qian; Xiong, Xingquan; Li, Sizhong; Catalysis Communications; vol. 58; (2014); p. 85 – 88;,
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Ester – an overview | ScienceDirect Topics

Related Products of 37466-90-3, 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 37466-90-3 as follows.

(1 13a) 2-(2,6-Dichloro-phenylamino)-1 H-benzimidazole-5-carboxylic acid A mixture of 3,4-diamino-benzoic acid ethyl ester (5.00 g, 27.8 mmol) and 1 ,3-dichloro-2- isothiocyanato-benzene (5.66 g, 27.8 mmol) in 40 ml. DMF was stirred for 2h under argon. DCC (5.72 g, 27.8 mmol) was added and mixture heated to 800C for 45 min. After stirring the mixture was diluted with water and concentrated /.vac. The residue was diluted with ethanol and 1 M NaOH (aq). The mixture was heated to 1000C and stirred overnight. Then ethanol was evaporated and the aq. phase was cooled, acidified with acetic acid, filtered and the solid washed with water. Yield: 8 g (90%)

According to the analysis of related databases, 37466-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; PFAU, Roland; ARNDT, Kirsten; DOODS, Henri; HAUEL, Norbert; KLINDER, Klaus; KUELZER, Raimund; MACK, Juergen; PRIEPKE, Henning; STENKAMP, Dirk; WO2010/34796; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 17100-65-1, A common heterocyclic compound, 17100-65-1, name is Methyl 2-bromo-4-methoxybenzoate, molecular formula is C9H9BrO3, 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.

Methyl 2-bromo-4-methoxybenzoate(45 mg, 1.4 equiv), BINAP (50 mg, 0.08 equiv), Pd (OAc) 2 (11.2 mg, 0.05 equiv) ), Toluene 20mL, N2 protection, 110 , the reaction 18h, filtered and the solvent was recovered, column chromatography to give a solid 165mg, yield 57%.

The synthetic route of 17100-65-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Shanghai Jiao Tong University; He Qiuqin; Yin Ming; Fan Renhua; Han Dandan; Zhou Kaiyi; Song Runzhe; Zhao Lu; (11 pag.)CN107056702; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics