Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, 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 18595-14-7, Formula: C9H11NO2

An autoclave was charged with a mixture of methyl 4-amino-3-methylbenzoate (10.0 g, 60.5 mmol, Cas No18595-14-7), rhodium 5% on charcoal (3.74 g, 50% wet), acitic acid (5.2 ml)and ethanol (100 ml) and pressurized with hydrogen (12 bar). The mixture was stirred at 80C for 22 h. For work-up, the catalyst was filtrate d off, washed with ethanol and the filtratewas concentrated under reduced pressure. The residue was dissolved in dichloromethane(250 ml) and hydrochloric acid (30 ml, 120 mmol, 4 M in dioxane) was added. The mixturewas concentrated und reduced pressure and the residue was codestilled with toluene (2x) togive the crude product as a mixture of isomers which was used without further purification.

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 64113-91-3, name is tert-Butyl 2-aminobenzoate, 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 64113-91-3, Product Details of 64113-91-3

To a solution of [4- (PHENYLMETHYL) PHENYL] acetic acid (0.059g, 0. 26MMOL, 1 EQUIV) and DIPEA (0. 054ML, 0. 31MMOL, 1.2equiv) in anhydrous DMF (0. 5MOI) was added a solution of HATU (0.119g, 0. 31MMOL, 1.2equiv) in DMF (0. 5M1), FOLLOWED by 1,1- dimethylethyl 2-aminobenzoate (0.060 g, 0. 31mmol, 1.2equiv) in DMF (0. 5ml). The mixture was stirred under an atmosphere of nitrogen for 72 hr, then concentrated under reduced pressure and partitioned between DCM and 2N HCI. The separated organic phase was washed with saturated sodium bicarbonate then evaporated under a stream of nitrogen and purified by preparative h. p. l. c. to give the title compound (0.033g, 32%) as a white solid ; LC/MS : m/z 402.2 [MH] +.

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/16870; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 52727-57-8, 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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 1a (18.60 g, 80.85 mmol) was dissolved in concentrated hydrochloric acid (200 mL, 12N), and an aqueous solution of sodium nitrite (6.69 g, 97.02 mmol) was slowly added dropwise at -10 to 0C. The reaction solution was at 0C. Stir for 1 hour. This reaction was added dropwise to a mixture of cuprous chloride (800 mg, 8.09 mmol) and sulfur dioxide (15.54 g, 242.55 mmol) at 0C. The resulting reaction solution was stirred at 0 C. for 1 hour and further warmed to 20 C. and stirred for 3 hours. After the reaction was completed, it was extracted with ethyl acetate (200 mL×3). The organic phases were combined, dried, concentrated to dryness under reduced pressure, and separated and purified by column chromatography on silica gel (petroleum ether/ethyl acetate=100-0%) to give Compound 1b (4.10 g).

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-amino-5-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (26 pag.)CN107987072; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 680217-71-4, 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 680217-71-4 as follows.

A mixture of scheme 27 compound 4 (1.4 g, 7.07 mmol) and (2,6-difluoro-phenyl)-acetic acid ethyl ester (2.63 g, 14.14 mmol), CS2CO3 (6.9 g, 21.2 mmol), were dissolved in DMF. The reaction mixture was heated to 110 C and stirred for 4h. The mixture was evaporated in vacuo, the residue was purified by silica gel column chromatography (DCM/MeOH = 100/1 to 10/1) to give the scheme 27 compound 5 (410 mg, 17%) as a yellow solid.

According to the analysis of related databases, 680217-71-4, the application of this compound in the production field has become more and more popular.

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

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 179688-27-8 as follows. Formula: C15H23NO6

To a stirred solution of 15.7 g (50 mmol) of ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate (Pfizer patent WO 96130347) in 50 ml of DMF at 0C was added phosphorous oxychloride (5.6 ml, 60 mmol) during 15 m. The resulting solution was heated at 55C for 45 m, cooled, diluted with methylene chloride, and treated at 0C with 200 ml of N/1 sodium hydroxide during 2 m. The organic layer was separated and washed at 0C with water. The solution was dried and evaporated with added toluene present to give 18.4 g of amber oil; NMR (CDCl3) delta 3.02 (s, Me2N).

According to the analysis of related databases, 179688-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth Holdings Corporation; EP973746; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 62451-84-7, name is Methyl 2-(3-(trifluoromethyl)phenyl)acetate, 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. name: Methyl 2-(3-(trifluoromethyl)phenyl)acetate

EXAMPLE 98; 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide; Step 1: A mixture of (3-trifluoromethyl-phenyl)-acetic acid methyl ester (6.0 g, 25.9 mmol) and N-bromosuccinimide (9.2 g, 51.7 mmol) and a few drops of hydrobromic acid (48% solution) in chloroform (250 mL) was heated under reflux for two days. The reaction mixture was concentrated to dryness, taken up in methylene chloride and loaded onto a column of silica gel. Elution with 5% ethyl acetate/hexanes gave Bromo-(3-trifluoromethyl-phenyl)-acetic acid methyl ester (3.0 g, 39% yield) as colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

The synthetic route of Methyl 2-(3-(trifluoromethyl)phenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brinkman, John A.; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Guertin, Kevin Richard; Marcopulos, Nicholas; Qi, Lida; Racha, Jagdish Kumar; Sarabu, Ramakanth; Tan, Jenny; Tilley, Jefferson Wright; US2007/270433; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 927-68-4, name is 2-Bromoethyl acetate, molecular formula is C4H7BrO2, 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. SDS of cas: 927-68-4

(2-Acetoxy-ethoxyimino)-[4-((1R,3R,7S)-9-bicyclo[3.3.1]non-3-yl-9-aza-bicyclo[3.3.1]non-3-yl)-3-oxo-3,4-dihydro-quinoxalin-2-yl]-acetic acid methyl ester (d26) To a suspension of d25 (331.0 mg, 0.672 mmol) in MeCN-DMF (2:1) (15 mL) was added 2-bromoethyl acetate (0.156 mL, 1.344 mmol) and K2CO3 (279 mg, 2.016 mmol) at a temperature of about 25 C. under a nitrogen atmosphere. The mixture was stirred at a temperature of about 25 C. for 6 hr and 60 C. for 3 hr. The reaction mixture was diluted with water-saturated aqueous NaHCO3 (1:1), then extracted with AcOEt-CHCl3 (4:1) (x2). The combined organic phases were washed with saturated aqueous NaCl, dried (Na2SO4), and concentrated. The resulting yellow amorphous solid was chromatographed (silica-gel 15 g, v/MeOH (10% concentrated NH4OH)=100/0?17/3) to provide 258.2 mg of d26 as a yellow solid. (Yield 66%) d26: 1H-NMR (300 MHz, CDCl3-CD3OD-DCl) delta: 1.28-3.05 (m, 27H), 3.89 (s, 3H), 4.02-4.13 (m, 2H), 4.13-4.25 (m, 1H), 4.26-4.31 (m, 2H), 4.47-4.53 (m, 2H), 6.37-6.54 (m, 1H), 7.39 (t, J=7.53 Hz, 1H), 7.79 (td, J=7.93, 1.37 Hz, 1H), 7.86 (dd, J=7.93, 1.51 Hz, 1H), 8.78 (d, J=8.69 Hz, 1H); LC/MS: m/z=579.4 [M+H]+ (Calc: 578).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 927-68-4, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; Purdue Pharma L.P.; MARRA, Jeffrey Michael; Tsuno, Naoki; Ueno, Tatsuhiko; Zhou, Xiaoming; US2014/187544; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 18013-97-3, 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. 18013-97-3, name is Diethyl 2,5-dibromoterephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 250 mL round bottom flask was charged with diethyl 2,5-dibromo-terephthalate (9.12 g, 24 mmol), 2-tri-n-butyltin-thieno[3,2-b]thiophene (25.76 g, 60 mmol) and tetratriphenylphosphine palladium (277.3 Mg, 0.24mmol). Nitrogen gas was purged three times, and toluene (120 mL) except oxygen was added, and the mixture was refluxed under nitrogen for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and dichloromethane was evaporated. The mixture was separated by silica gel column chromatography using dichloromethane as eluent to give diethyl 2,5-bis(thieno[3,2-b]thiophen-2-yl)terephthalate (8.98 g, yield 75%).

The synthetic route of Diethyl 2,5-dibromoterephthalate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Ningbo Materials Technology And Engineering Institute; Fang Junfeng; Zhang Wenjun; Song Changjian; (26 pag.)CN109232604; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 39149-80-9, 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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows.

yl)propanoate (R)-6-chloro-4-(3-methylpiperazin-1-yl)pyridazin-3-amine (370 mg, 1.62 mmol) (prepared as in example G02939250) was dissolved in dimethylformamide (8 mL) for the addition of tert-butyl 2-bromopropanoate (0.44 g, 2.11 mmol), followed by potassium carbonate (0.45 g, 3.24 mrnol). The solution was heated to 60 C for 72 h. The reaction mixture waspartitioned between ethyl acetate and sodium bicarbonate (aq., sat.). The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (eluting with hexanes and ethyl acetate) to afford the title compound (0.42 g, 1.19 mmol, 73%). LCMS I41Z (M+H) 356.

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 4934-99-0, 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. 4934-99-0 name is Methyl 3-hydroxycyclobutanecarboxylate, 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.

General procedure: To a flask containing alcohol (3 equiv.) in THF (0.1 – 0.5 M) at 0 C was added sodium hydride (3 equiv. 60% oil immersion). The resulting slurry was stirred 10 min and the alkyl bromide (1 equiv.) was added. The reaction mixture was allowed to reach rt and was stirred 2 h at which point NH4CI solution (saturated, 10 mL) was added followed by EtOAc (10 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (3 x 10 mL). The combined organic layers were dried over anhydrous MgSOr, filtered and concentrated under reduced pressure and purified employing either silica gel flash chromatography (0-> I 00% EtO Ac/hexanes) or reverse-phase preparatory HPLC (Phenomenex Luna 10 m C18, 100A,150 x 30 mm, 5 ->95% MeCN (0.1% formic acid) in H2O, 25 min, 60 mL/min) to afford the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-hydroxycyclobutanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; DENALI THERAPEUTICS INC.; CRAIG, Robert A., II; DE VICENTE FIDALGO, Javier; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian M.; LEXA, Katrina W.; OSIPOV, Maksim; SWEENEY, Zachary K.; THOTTUMKARA, Arun; (137 pag.)WO2019/183589; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics