Tag: M.W=200-300

Application of 106896-49-5, The chemical industry reduces the impact on the environment during synthesis 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI2(dppf) as a catalyst, created compounds 51a followed by reductive amination utilizing N-Boc- aminoacetaldehyde produced compounds 52a-c. A series of deprotections followed by guanidinylation of the resulting amine afforded the N-terminal portions of the inhibitor 53a-c. The C-terminal hydrophobic portion of the molecule was synthesized via alkylation of A- nitroaniline with the corresponding bromide and subsequent reduction of the nitro group utilizing tin (II) chloride, producing compounds 55a-i. Coupling of compounds 53a-c and 55a- i followed by Boc deprotection under acidic conditions produced inhibitors 56aa-ci. Inhibitors64a-b were derived from a similar synthesis, but in place of the reductive amination step, 48c was reacted with Boc-Gly-OH to provide the amide intermediate compound 62 which was manipulated in a similar manner to provide inhibitors 64a-b, seen in Figure 16.The synthesis of inhibitors 57aa-fa was designed to employ a late stage Suzuki coupling to provide faster access to a number of derivatives at the R1 position, while keeping R2 as a benzyl substituent, see Figure 15. Commercially available methyl-4-amino-3-bromobenzoate was saponified under basic conditions followed by amide bond formation with compound 55a to provide compound 59a. This intermediate was then reacted with different boronic acid derivatives PdCI2(dppf) as a catalyst to provide 60aa-fa. A series of functional group transformations provided inhibitors 57aa-fa. The indole scaffold was readily derived from commercially available 4-iodoaniline and Boc- GIy-OH, which were reacted to form iodo-amide compound 65, seen in Figure 17. Sonagashira cross-coupling of compound 65 and ethynyl-trimethyl-silane (TMS-acetylene) followed by removal of the silyl protecting group afforded terminal alkyne compound 66. A consecutive Sonagashira cross-coupling with 2-iodo-4-nitroaniline followed by cycloisomerization employing catalytic copper (II) acetate41 afforded indole scaffold compound 68. Reduction of the nitro to the amine followed by alkylation with the cooresponding bromide provided compound 70a-b. A series of functional group transformations, similar to the reactions depicted in Figures 10 and 13, provided inhibitors 71a-b. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween. Now that the invention has been described,

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

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; YALE UNIVERSITY; WO2008/70823; (2008); A2;,
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Adding a certain compound to certain chemical reactions, such as: 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, 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 24393-53-1, category: esters-buliding-blocks

Example 1; 4′-((1S.2SV2-ir(2S)-2-MethylPyrrolidin-1-v?methyllcvcloproDvn-1.1′-biphenyl-4- carbonitrile; Example 1A; fra/7S-3-(4-Bromophenyl) prop-2-en-1 -ol; To a solution of ethyl trans-4-bromocinnamate (8 ml_, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C dropwise. After the addition, the mixture was allowed to warm from -78 0C to -30 0C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added till acidic (pH=2). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried withMgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz1 1H)1 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz, J =3 Hz, 1H), 7.25 (d, J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.; Example 26; 4′-(f1R.2S)-2-(2-ff2R)-2-Methylpyrrolidin-1-yl1ethyl>cvclopropyh-1.1′-biphenyl-4- carbonitrile; Example 26A; 3-(4-BromophenvQprop-2-ene i-p|; To a solution of ethyl trans-4-bromocinnamate [CAS 24393-53-1] (8 mL, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added dropwise diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C. Following the addition, the mixture was allowed to warm from -780C to -300C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added. The organic layer was separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz, 1 H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt. J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz1 J =3 Hz, 1H), 7.25 (d. J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H); Example 34; 2-r4-((1S.2S)-2-(f(2S)-2-MethylPyrrolidin-1-yllmethyl)cvclopropyhphenyllPyridazin- 3(2H)-one; Example 34A; (E)-3-(4-bromophenyl)prop-2-en-1-ol; To a solution of (E)-ethyl 3-(4-bromophenyl)acrylate (25 g, 96 mmol) inDCM (300 ml) under nitrogen and cooled to -78 0C was added dropwise DIBAL-H (240 ml, 1 M in DCM, 240 mmol) in about 20 minutes. The mixture was stirred at -780C for 2 hours. Then, the dry ice bath was removed. The reaction was diluted with DCM (500 ml_), quenched with HCI (1N), and partitioned. The combined organic phases were washed with HzO, dried and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.43 (t, J = 6 Hz1 1H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz, 1H), 6.57 (d, J =15 Hz, 1H), 7.25 (d, J = 9 Hz, 2H)1 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Ethyl 3-(4-bromophenyl)acrylate, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/150010; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 148547-19-7, 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 148547-19-7 as follows.

To a solution of methyl 4-bromo-3-methylbenzoate (ABCR, 15 g, 65 mmol) in toluene (200 ml.) and water (200 ml_), was added o-tolylboronic acid (10.68 g, 78 mmol) followed by potassium carbonate (45.25 g, 32.7 mmol) and Pd(PPh3)4 (3.78 g, 3.3 mmol). The mixture was degassed with N2 and refluxed at 1200C for 6 hours. After the completion of reaction, the reaction mixture was cooled to RT. The organic phase was separated and evaporated under reduced pressure. The crude compound was passed through a silica column (60-120) using hexane as eluent to get the title compound as a white solid (15 g, 95%). 1H NMR (DMSO-dbeta, 400 MHz) delta 7.91 (s, 1 H), 7.83-7.81 (m, 1 H), 7.33-7.30 (m, 2H), 7.28-7.26 (m, 1 H), 7.25-7.22 (m, 1 H), 7.07-7.05 (d, 1 H), 3.86-3.81 (s, 3H), 2.09-2 (s, 3H), 1.97-1.92 (s, 3H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; GERBER, Patrick; DORBAIS, Jerome; WO2010/100142; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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.

Compound 422 (0.50 g, 1.0 mmol) and DIPEA (0.4 mL, 2.4 mmol) were dissolved in DCM (5.0 mL) at 0 , and then compound 301 (0.23 g, 1.0 mmol) was added. The reaction was stirred at 0 for 2.5h, then concentrated and purified by SiO2column to give the title product 423 (0.30 g, 43%) . ESI m/z calcd for C31H45N5O11P [M+H]+: 694.28, found 694.28.

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
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Reference of 25542-62-5, A common heterocyclic compound, 25542-62-5, name is Ethyl 6-bromohexanoate, molecular formula is C8H15BrO2, 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 26; ethyl 6-{5-cyarto-1H-indol-1-yi)hexanoate; [00233] Cyanoi?dole ( 500 mg, 3.52 mmol ) was added to a suspension of sodium hydride (1.1 eq. 148 mg of 60% dispersion m mineral oii) in dimethylformamide and the reaction was stirred for 10 min. Then ethyl 6-bromohexanoate (1 5 eq, 1.18 g, 5.28 mmol ) was added dropwsse. The reaction was stirred at ambient temperature for 5 hours. Then water (8 :1) added and this was extracted with ethyl acetate. The ethyl acetate solution was concentrated in vacio and the residue was purified by silica gel column using ethyl acetate/ hexane as an eluting solvent to afford ethyl 6-{5-cyano~1 H-indol-1- yl)bexanoate (850 mg, 85% yield). 1H NMR {300 MHz, d6-DMSO): delta 8.057(d, J=1.172 Hz1 1H), 7.65(d. J=8.793 Hz. 1H), 7.6(d, J=2.93 Hz, 1H), 7.5(dd, J=1.759Hz, 8.79Hz, 1H), 6.6(d, J=3,5 Hz, 1H), 4.2(t, J=7.03 Hz, 2H), 3.98{q, J=7.034 Hz, 2H), 2.2(t, J=7.3, 2H)1 1.72(pent, J=7.62 Hz, 2H), 1.5(pe?t, J=7.62 Hz, 2H), 1.2( m, 2H)1 1.1(1, J=7.034 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; NUADA, LLC; WO2007/134169; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 13078-21-2, These common heterocyclic compound, 13078-21-2, name is Ethyl 2-(2-methoxyphenoxy)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.

General procedure: A mixture of phenols (0.3 mmol), acetone (10 ml), dimethylformamide(10 ml), ethyl chloroacetate (2.5 ml, 0.26 mmol), potassiumcarbonate (2 g) and potassium iodide (0.15 g) was heated at75 C for 12 h. Afterwards, the solid was filtered and the solventof the filtrate was removed in vacuo. The colorless liquid (4a-f)obtained was dissolved in ethanol (20 ml). A solution of potassiumhydroxide (7.2%, 5 ml) was added and stirred at room temperaturefor 1.5 h. The mixture was poured into hydrochloric acid (1 mol/L)and a white precipitate was formed. Purification by recrystallizationfrom methanol afforded the corresponding aryloxyl acid (5a-f)

The synthetic route of 13078-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4428 – 4433;,
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. 19063-55-9, name is 6-Bromochromen-2-one, A new synthetic method of this compound is introduced below., Quality Control of 6-Bromochromen-2-one

(1) Weigh 5.2 g of DL-malic acid (38.78 mmol) in a SCHLENK reaction tube.10 g of m-bromophenol (58.17 mmol) was added under N2 atmosphere.13mL of 98% concentrated sulfuric acid was added dropwise with stirring in an ice bath.The reaction was stirred at 120 C for 6 h. After the reaction, cool to room temperature.The reaction solution was slowly dropped into a stirred saturated saline solution, and filtered to give a solid.It was redissolved in dichloromethane, washed with water three times, and the organic phase was dried over anhydrous sodium sulfate.concentrate. Separated and purified by silica gel column chromatography.The mobile phase was petroleum ether/dichloromethane = 3/2. Finally, both Br-C5 and Br-C7 were obtained as white solids, respectively 1.60 g, 5.66 g.

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; Xi’an Jiaotong University; Zhou Guijiang; Feng Zhao; Yang Xiaolong; (40 pag.)CN109608502; (2019); A;,
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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6BrFO2

4-chloro-2, 6-dimethylphenol (0.672 g, 4.29 mmol), methyl 3 -bromo-4-fluorobenzoate(1.0 g, 4.29 mmol) and cesium carbonate (2.097 g, 6.44 mmol) were combined in dimethylsulfoxide (4.29 mL) under argon in a sealed tube and heated at 80 C for 3 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by chromatography (silica, 0-30 % ethyl acetate in heptanes)provided the title compound (1.57 g, 93 %).

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

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; HASVOLD, Lisa A.; LIU, Dachun; MCDANIEL, Keith F.; PRATT, John; SCHRIMPF, Michael; SHEPPARD, George S.; WANG, Le; LI, Bing; (191 pag.)WO2017/177955; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

46064-79-3, name is Methyl 3-amino-4-bromobenzoate, 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: C8H8BrNO2

Benzoyl isothiocyanate (3.12 g, 19.1 mmol) was added to a stirred mixture ofmethyl 3-amino-4-bromobenzoate (4.0 g, 17.4 mmol) in acetone (40 ml) and the mixture was stirred at 60C for 6 hr. After being cooled to room temperature, the reaction mixture was evaporated under vacuum. The residue was purified by column chromatography on silica gel Isolute Flash Si; 50 g prepacked, eluted with EA/PE (0-30%) to give the title compound: LCMS (ESI) calc?d for C,6H,3BrN2O3S [M + H]: 393, 395 (1:1), found 393, 395 (1:1); ?H NMR (400 MHz, DMSO-d6): oe12.65 (s, 1H), 11.91 (s, 1H), 8.47 (d, J= 2.0 Hz, 1H), 8.02-8.00 (m, 2H), 7.92-7.91 (m, 1H), 7.81-7.80 (m, 1H), 7.78-7.69 (m, 1H), 7.58-7.54 (m, 2H), 3.88 (s, 3H).

The synthetic route of 46064-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, 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. Application In Synthesis of Diethyl 2-(1-ethoxyethylidene)malonate

Reference Example 196 Ethyl 4-hydroxy-6-methylpyrimidine-5-carboxylate A mixture of diethyl malonate (4.8 mL), triethyl orthoacetate (17 mL), acetic anhydride (0.11 mL) and zinc chloride (1.2 g) was stirred at 140C. To the mixture was added acetic anhydride (0.11 mL) each after 30, 90 and 120 minutes, and then stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 4/1 – 7/3) to give diethyl 2-(1-ethoxyethylidene)malonate (5.02 g). To a solution of diethyl 2-(1-ethoxyethylidene)malonate (4.13 g) in ethanol (15 mL) were added formamidine hydrochloride (1.73 g) and a solution of potassium hydroxide (2.21 g) in water (7.5 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was neutralized by adding acetic acid. To the mixture was added ethyl acetate (30 mL), and the mixture was stirred at room temperature for 30 minutes. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate – ethyl acetate/methanol = 9/1) to give the title compound (1.5 g).

The synthetic route of Diethyl 2-(1-ethoxyethylidene)malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics