Month: August 2021

Synthetic Route of 35180-01-9, The chemical industry reduces the impact on the environment during synthesis 35180-01-9, name is Chloromethyl isopropyl carbonate, I believe this compound will play a more active role in future production and life.

To a solution of 4-{3-[3-bromo-4-(difluorophosphonomethyl)benzyl]-2-imino-2,3-dihydro-thiazol-4-yl}benzoic acid (600 mg, 1.14 mmol) in 8 mLN,N-dimethylformamide under nitrogen atmosphere was added diisopropyl ethylamine (0.99 mL, 5.7 mmol) followed by 708 mg (4.62 mmol) of 1-chloromethyl isopropyl carbonate (prepared according to the procedure in EP 0 682 023) and catalytic amount of Nal (80 mg, 10 mol %). The mixture was stirred at 60 C for 14 hours. Solvent wasevaporated under reduced pressure. The residue was dissolved in 30 mL dichloromethane and washed with 20 mL water followed by 20 mL brine, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified on silica gel column using dichloromethane (400 mL), 25:1 dichloromethane : ethanol (600 mL) and 15:1 dichloromethane : ethanol (600 mL) and then 12:1 dichloromethane : ethanol to elute the compound. Fractions containing pure compound were combined and evaporated to obtain 275 mg (32 %) of title compound..H NMR (CDC13, 600 MHz): 5 (ppm) 1.31 (s, 12H), 4.50 (s, 2H), 4.94 (m, 1H), 4.96 (m, 1H), 5.61 (s, 2H), 6.00 (s, 2H), 6.84 (s, 1H), 7.28-8.07 (m, 7H); MS (ESI): m/z 750 (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, Chloromethyl isopropyl carbonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CENGENT THERAPEUTICS, INC.; WO2006/28970; (2006); 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. 680217-71-4, name is Ethyl 2-(2,6-difluorophenyl)acetate, A new synthetic method of this compound is introduced below., Product Details of 680217-71-4

As in the scheme, a solution of scheme 28 compound 1 (1 g, 3.95 mmol), ester (1.47 g, 7.9 mmol) and CS2CO3 (3.86 g, 11.85 mmol) in DMF (30 mL) under N2 was added and stirred at 110 C for 4 h. The solvent then was evaporated and the remaining residue was diluted with water and extracted with CH2C12. The combined extracts were washed with brine, dried over Na2S04 and concentrated in vacuo. The crude product was purified by prep-HPLC to afford scheme 28 compound 2 (420 mg, 27.4%) as a brown solid.

The synthetic route of 680217-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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 816-27-3, Product Details of 816-27-3

2-(3-Chloroquinolin-6-yl)acetohydrazide (170.0 mg, 0.723 mmol, 1.0 eq) and ethyl 2-ethoxy-2-iminoacetate (231.0 mg, 1.591 mmol, 2.0 eq) in ethanol (20.0 mL) were stirred at 30 C for 72.0 h. The solvent was removed in vacuo, to provide (Z)-ethyl 2-amino- 2-(2-(2-(3-chloroquinolin-6-yl)acetyl)hydrazono)acetate (242.0 mg, ca. 100%).

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, Ethyl 2-ethoxy-2-iminoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1Atert-Butyl 1-(3-bromobenzyl)cyclopropanecarboxylate; Under argon, 14.8 ml (105.48 mmol) of diisopropylamine were initially charged in 66 ml of dry THF, and the mixture was cooled to -40 C. 42.2 ml (105.48 mmol) of n-butyllithium solution (2.5 M in hexane) were slowly added dropwise and the mixture was stirred for 30 min. The reaction solution was then cooled to -78 C., and a solution of 10.0 g (70.32 mmol) of tert-butyl cyclopropanecarboxylate in 17 ml of THF was added. After 4 h of stirring at -78 C., a solution of 19.34 g (77.36 mmol) of 3-bromobenzyl bromide in 17 ml THF was added. The reaction mixture was slowly warmed to RT overnight, and aqueous ammonium chloride solution was then added carefully and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on 750 g of silica gel (mobile phase cyclohexane/dichloromethane 50:1, then 5:1). This gave 13.3 g (60.7% of theory) of the title compound.GC-MS (Method 1): Rt=5.94 min; m/z=256 (M-C4H8)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=7.46 (s, 1H), 7.38 (m, 1H), 7.25 (m, 2H), 2.82 (s, 2H), 1.28 (s, 9H), 1.08 (q, 2H), 0.87 (q, 2H).

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, tert-Butyl cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – 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. 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H16O4

Preparation method: In air atmosphere,Add 0.2 mmol of N-pyrimidindolline compound to the microwave reaction tube,0.2 mmol of ethylene cyclopropane compound,0.006mmol of [Ru (p-cymene) Cl2] 2,0.06 mmol of mesitylene,0.04mmol of silver hexafluoroantimonate, microwave reaction at 40 C for 2 hours;After completion of the reaction, rinse with ethyl acetate.Chromatographic separation after concentration under reduced pressure (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to 100/0)Dried to a pale yellow oil,Yield 75%, E / Z = 11: 1.

According to the analysis of related databases, 7686-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhengzhou University; Henan Communication Polytechnic College; Zhu Xinju; Wang Qiuling; Xie Xiaona; Zhang Xiaojie; Yan Jing; Xu Yan; Hao Xinqi; Song Maoping; (15 pag.)CN110551106; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6627-89-0,Some common heterocyclic compound, 6627-89-0, name is tert-Butyl phenyl carbonate, molecular formula is C11H14O3, 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.

A solution of 0.48 mL (3.8 mmol) of 4-bromo-lH-indole in 1 mL of THF was added to a suspension of 0.15 g (6.3 mmol) of NaH in 5 mL of THF, followed by 1.2 mL (6.3 mmol) of tert-butyl phenylcarbonate. The reaction solution was stirred 18 h, then quenched with1 mL of iPrOH, poured into 100 mL of Et2O and washed twice with a saturated aqueous solution of NH4Cl and thrice with water. The organic solvent was removed in vacuo and the residue was purified by flash chromatography eluting with neat hexane to yield the title compound. MS (M-BOC+2H)+ 196.

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 phenyl carbonate, its application will become more common.

Reference:
Patent; AMGEN, INC.; WO2006/66172; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 37722-82-0, A common heterocyclic compound, 37722-82-0, name is Methyl 3-Hydroxycyclohexanecarboxylate, molecular formula is C8H14O3, 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 the solution of methyl 3-hydroxycyclohexanecarboxylate AA53 (25.7 g, 0.163 mmol) in dichloromethane (250 mL) was added Dess-Martin periodinane (69.0 g, 0.163 mmol) over 20 minutes at 0 . After stirred at room temperature for 3 hours, the mixture was filtered. The filtrate was washed with saturated sodium bicarbonate aqueous solution (200 mL) for three times, brine (200 mL) , dried over Na2SO4 (s), filtered and concentrated to give a residue, which was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 15 : 1 to 6 : 1) to give the title compound (20.5 g, 82 %yield) as colorless oil.1H NMR (400 MHz, CDCl3) delta 3.70 (s, 3H) , 2.84 -2.76 (m, 1H) , 2.54 (d, J = 10.4 Hz, 2H) , 2.37 -2.27 (m, 2H) , 2.13 -2.02 (m, 2H) , 1.90 -1.70 (m, 2H) .

The synthetic route of 37722-82-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UNLIMITED COMPANY; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; JIANG, Yimin; WAN, Zhao-Kui; CHEUNG, Wing Shun; LIU, Qian; DENG, Gang; LIANG, Chao; (230 pag.)WO2019/214610; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87808-49-9, 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. 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-bromo-4-methylbenzoate (50.0 g, 218 mmol) in perchloromethane (500 mL) was added 2,2′-(diazene-l,2-diyl)bis(2-methylpropanenitrile) (3.58 g, 21.8 mmol) and l-bromopyrrolidine-2,5-dione (42.7 g, 240 mmol). The mixture was stirred at 70 C for 12 hrs. On completion, the reaction mixture was cooled to it and filtered. The filtrate was concentrated under reduced pressure to afford the title compound which was used into the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (358 pag.)WO2017/156165; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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. COA of Formula: C9H11NO3

Description 20: Methyl 4-{[(2-fluorophenyl)carbonyl]amino}-2-(methyloxy)benzoate; Methyl 4-amino-2-(methyloxy)benzoate (10.0 g, 55.2 mmol) was suspended in dichloromethane (50 ml_), cooled in an ice bath and treated dropwise with diisopropylethylamine (10.57 ml_, 60.8 mmol) followed by 2-fluorobenzoyl chloride (7.25 ml_, 60.8 mmol). The mixture was allowed to warm to room temperature and stirred under argon for 2.5 hours. The solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine. The ethyl acetate layer was separated. A solid came out of solution upon standing. This was collected by filtration to give the title compound. LC/MS (ES+ve): [M+H]+ at m/z 304 (C16H14FNO4 requires [M+H]+ at m/z 304).

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/138033; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 52727-57-8,Some common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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.

3- (morpholin-4-ylsulfonyl) benzoic acid (271 mg, 1.0 mmol) was suspended in [CH2C12] (10 mL) and (COCl) 2 added (725 mg, 5.7 mmol). A catalytic amount [OF DMF] was then added and the mixture stirred for 4 hrs. The solvent was then removed in vacuo to give the acid chloride as an oil. The oil was dissolved in [CHC13] (10 mL). Methyl 2- amino-5-bromobenzoate (230 mg, 1.0 mmol) was added followed by pyridine [(1] mL). The solution was stirred at room temperature for an additional 12 hrs then poured into 1 M HC1 (20 [ML)] and extracted with EtOAc (3 x 20 mL). The combined organic solutions were dried over Na2S04 and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (20% EtOAc in hexane) to provide 367 mg of the desired methyl ester (76%). The ester was treated with [LIOH] in 1: 1: 1 THF/MeOH/H20 for 12 hrs followed by acidification and extraction with EtOAc. The organic solution was dried over NazS04 and then concentrated in vacuo. The title compound (328 mg, 92%, 70% overall) was obtained as a white solid after recrystalization from [MEOH.] H NMR (400 MHz, DMSO) 2.93 (m, [4H),] 3.65 [(M,] 4H), 7.88 (dd, 1H), 7.90 (d, 1H), 8.00 (d, [1H),] 8.13 (d, 1H), 8.25-8. 29 [(M,] [2H),] 8. 59 (d, 1H), 12.21 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-5-bromobenzoate, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics