Tag: M.W=200-300

These common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 tert-Butyl 9-Amino-4,7-dioxanonanoate

SI-22 (270 mg, 1.03 mmol, 1.2 eq.), COMU (440 mg, 1.03 mmol, 1.2 eq.), and N- methylmorpholine (283 pL, 2.57 mmol, 3 eq.) were dissolved in 1.5 mL of DMF and stirred for 1 min. Amino-PEG2-t-butyl ester (200 mg, 0.86 mmol, 1 eq.) was added in 2.5 mL of DMF and the reaction was stirred at room temperature for 1 h. The reaction was diluted with ethyl acetate (lOmL) and the organic phase washed with water (3xl5mL) and brine (lxl5mL). The organic layer was separated, dried over anhydrous MgSCE, and concentrated. The residue was purified by flash chromatography (DCM/EtOAc; 1 : 1) to provide the title compound as a colorless oil (212 mg, 43%). NMR (500 MHz, Chloroform-7) d 7.01 (t, J= 5.7 Hz, 1H), 6.71 (dt, J= 8.7, 2.4 Hz, 1H), 6.68 (s, 1H), 4.43 (s, 2H), 3.74 – 3.69 (m, 2H), 3.67 (td, J= 6.4, 2.0 Hz, 2H), 3.55 (d, j= 2.3 Hz, 4H), 3.51 (ddd, j= 6.5, 3.4, 1.5 Hz, 2H), 2.65 (s, 2H), 2.48 – 2.40 (m, 4H), 2.18 (qd, J= 7.6, 2.1 Hz, 1H), 1.90 (td, j= 6.6, 1.8 Hz, 2H), 1.41 (d, 7= 1.5 Hz, 2H), 1.40 (d, 7= 2.3 Hz, 9H), 1.11 (td, 7= 7.8, 2.6 Hz, 3H). HRMS (ESI) [M+Na]+ for C25H38N207Na 501.2571, found 501.2580.

The synthetic route of tert-Butyl 9-Amino-4,7-dioxanonanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; ZHANG, Xiaoyu; CROWLEY, Vincent; CRAVATT, Benjamin; (121 pag.)WO2020/77278; (2020); A1;,
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Reference of 99548-55-7,Some common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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.

i 4-Bromo-2-bromomethylbenzoic acid, methyl ester The subtitle compound was prepared from 4-bromo-2-methylbenzoic acid methyl ester (22.5 g) according to the method of example 2 step (i). Yield 26.45 g. Used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; AstraZeneca U.K. Limited; US6162808; (2000); A;,
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Adding a certain compound to certain chemical reactions, such as: 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 756525-95-8, Formula: C11H23NO4

Preparation of (9H-fluoren-9-yl)methyl 2-((1-(3-(4-((2-(2-(3-(tert-butoxy)-3- oxopropoxy)ethoxy)ethyl)amino)piperidin-1-yl)-3-oxopropyl)-1H-indol-2-yl)methyl)-1,2- dimethylhydrazine-1-carboxylate (Fmoc-HIPS-PAPip(PEG2(CO2t-Bu))NH) (Figure 62) To a dried scintillation vial containing a magnetic stir bar was added Fmoc-HIPS- piperidinone (355 mg, 0.63 mmol), H2N-PEG2-COOtBu (175 mg, 0.76 mmol), 4 A molecular sieves (activated powder, 100 mg), and 1,2-dichloroethane (2.5 mL). The mixture was stirred for 1 h at room temperature. To the reaction mixture was added sodium triacetoxyborohydride (314 mg, 1.48 mmol). The mixture was stirred for 18 hours at room temperature. The resulting mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with saturated aqueous NaHCO3 (2 x 5 mL), and brine (1 x 5 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield the title compound as a yellow oil, which was carried forward without further characterization.

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; REDWOOD BIOSCIENCE, INC.; RABUKA, David; ALBERS, Aaron Edward; KUDIRKA, Romas Alvydas; GAROFALO, Albert W.; WO2015/81282; (2015); A1;,
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Related Products of 75567-84-9, 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. 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In distinct reactors, 3-(bromophenyl)-propionic methyl esters 16, 17 (1.0 equiv) were dissolved in toluene (7 mL). Phenyl boronic acids 18-21 (2 equiv) in EtOH (3.5 mL) and Na2CO3 2 M (2 M, aq, 3.0 equiv) were then added to the corresponding reactors, and the resulting mixtures were deoxygenated with a stream of N2. After 10 min, Pd(PPh3)4 (0.005 equiv) was added and each mixture was stirred at reflux temperature for 5 h under N2, then cooled to room temperature and treated as follows. Each solution was poured into a mixture of H2O (5 mL) and Et2O (5 mL), and the two phases were separated. The aqueous layer was washed with Et2O (5 mL), and the organic phases were combined and washed with 1 M NaOH (5 mL), followed by brine (5 mL), then dried over Na2SO4 and evaporated. Purification of each crude product performed by flash chromatography on silica gel (petroleum ether/EtOAc = 8/2) yielded the corresponding biphenyl propanoic acid methyl esters 22a-e (Scheme 3).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-(4-bromophenyl)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chiriano, Gianpaolo; De Simone, Angela; Mancini, Francesca; Perez, Daniel I.; Cavalli, Andrea; Bolognesi, Maria Laura; Legname, Giuseppe; Martinez, Ana; Andrisano, Vincenza; Carloni, Paolo; Roberti, Marinella; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 206 – 213;,
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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 618-89-3 as follows. Formula: C8H7BrO2

To a soiuiion of Compound 5-1 (2,00 g, 9.30 mmol, 1.00 eq) and morpholine (972 mg, 1 1.2 mmol, 1.20 eq) in toluene (20 n L) was added Cs2Ci (6.10 g, 1 8.6 mmol 2.00 eq), BINAP (289 mg, 465 umol, 0,05 eq) and Pd(OAe)2 (104 mg, 465 umo, 0.05 eq). The mixture stirred at 100 C in N2 atmosphere for 1 8 hr. The solid was filtered off and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (PE:EtOAc=10: 1 to 5: 1 ) to afford Compound 6-2 (1.40 g, 69% yield) as a colorless oil. ‘HNMR: (400 MHz, CDCb) delta 7.607 (s, 3H), 7.567 (d, J=8 Hz, IH), 7.357 ( =4 Hz, I H), 7.134-7.128 (m, 4H), 3.930 (s, 3H), 3.897 (t, J-4.8 Hz, 4H), 3.230 (t, J=4.8 Hz, 4H).

According to the analysis of related databases, 618-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF UTAH RESEARCH FOUNDATION; VANKAYALAPATI, Hariprasad; SHARMA, Sunil; LIU, Xiaohui; COBURN, Craig; (106 pag.)WO2017/4519; (2017); A1;,
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Some common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, 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. HPLC of Formula: C7H13BrO2

3,5-Dimethyl-4-(3-phenyl-1H-indol-5)-isoxazole (0.5 g, 1.75 mmol) was weighed and dissolved in 30 ml of acetonitrile.Cesium carbonate (2.5 g, 5 mmol) was added, and then methyl 6-bromohexanoate (0.41 g, 2.0 mmol) was added dropwise thereto, and the mixture was reacted at 70 ¡ã C for 2 h.After completion of the reaction, ethyl acetate was extracted (40 ml ¡Á 3), and the organic phase was combined and washed with a saturated sodium chloride solution.Dry over anhydrous sodium sulfate overnight. After filtration, the solvent was evaporated under reduced pressure and purified by column chromatography.A white solid was obtained in an amount of 0.38 g, yield 84percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14273-90-6, its application will become more common.

Reference:
Patent; Shenyang Pharmaceutical University; Liu Dan; Zhao Linxiang; Yang Jinyu; Cheng Gaoliang; Bao Yu; Jing Yongkui; (20 pag.)CN109096272; (2018); A;,
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Related Products of 152849-72-4, 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. 152849-72-4, name is Methyl 5-bromo-2,4-dimethylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: methyl 5-(1-(2-(difluoromethoxy)phenyl)piperidin-4-ylamino)-2,4-dimethylbenzoate 1-[2-(difluoromethoxy)phenyl]piperidin-4-amine (240 mg, 990 umol), methyl 5-bromo-2,4-dimethyl-benzoate (240 mg, 990 umol), Pd2(dba)3 (54 mg, 59 umol), BrettPhos (73 mg, 118 umol), Cs2CO3 (450 mg, 1 mmol) in toluene (5 mL) was stirred at 90 C. for 16 h. The mixture was filtered by celite, the filtrate was concentrated and was purified via silica gel chromatography eluting with PE/EA from 50/1 to 20/1 to obtain methyl 5-[[1-[2-(difluoromethoxy)phenyl]-4-piperidyl]amino]-2,4-dimethyl-benzoate (200 mg, 49.92%) as white solid. ESI-MS (EI+, m/z): 405 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 5-bromo-2,4-dimethylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
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Synthetic Route of 136333-97-6, The chemical industry reduces the impact on the environment during synthesis 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, I believe this compound will play a more active role in future production and life.

[8911 Step 1: Synthesis of methyl4-(2-((3R.55?)-4-benzvl-3 .5-dimethvlpiperazin- 1 -vflethvl?)benzoate [8921 (2S,6R)-1-benzyl-2,6-dimethylpiperazine (formula 8-3, 0.200 g, 0.83 1 mmol) and DIPEA (0.363 mL, 2.077 mmol) were dissolved in acetonitrile (5 mL), and methyl 4-(2-bromoethyl)benzoate (formula 8-4, 0.404 g, 1.66 1 mmol) was added thereto at room temperature. The mixture was stirred at 60 C for 17 hours, and then water was added to the reaction mixture, followed by extraction with methylene chloride. The extract was passed through a plastic filter to remove solid residue and an aqueous layer, and the organic layer was concentrated under reduced pressure. The concentrate was concentrated by column chromatography (silicon dioxide; ethyl acetate/hexane = 25 %) and concentrated to afford the desired compound (0.075 g, 24.6 %) as a pale yellow oil.

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-(2-bromoethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; SONG, Hyeseung; LEE, Changgon; KWAK, Dalyong; LEE, Jaeyoung; BAE, Suyeal; KIM, Yuntae; BAE, Daekwon; HA, Nina; BAE, Miseon; KIM, Jihyun; WO2015/137750; (2015); A1;,
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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. 214470-85-6, name is Methyl 2-amino-5-ethoxy-4-methoxybenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-amino-5-ethoxy-4-methoxybenzoate

Example 92 6-Ethoxy-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile A solution of 10.2 g (45.3 mmol) of methyl 2-amino-5-ethoxy-4-methoxy benzoate and 10.8 g (90.7 mmol) of dimethylformamide dimethyl acetal in 50 mL of dimethylformamide was refluxed for 3 h. Volatile material was removed and the residue was azeotroped with toluene and dried in vacuo to give the formamidine as a purple syrup. n-Butyllithium (100 mmol) in hexane was diluted with 60 mL of tetrahydrofuran at -78C. A solution of 4.18 g (102 mmol) of acetonitrile in 80 mL of tetrahydrofuran was added over 15 min and the solution was stirred for 20 min. The crude formamidine was dissolved in 80 mL of tetrahydrofuran and added dropwise to the cold solution over 0.5 h. After stirring for 2h, the reaction was quenched at -78C with 13 mL of acetic acid. It was allowed to warm to room temperature and volatile material was removed in vacuo. The residue was slurried with water and the crude product was collected by filtration washed with water and dried. This material was then washed with chloroform and dried to give 7.95 g of 6-ethoxy-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile as yellow crystals: mass spectrum (electrospray, m/e): M-H 243.2.

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; Wyeth Holdings Corporation; EP1263503; (2005); B1;,
Ester – Wikipedia,
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Electric Literature of 35120-18-4, 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. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-fluoroquinoline-4-thiol 12b (100 mg, 0.56 mmol), ethyl 1-bromocyclobutanecarboxylate (139 mg, 0.67 mmol) and cesium carbonate (545 mg, 1.67 mmol) were added to 5 mL of N,N-dimethylformamide, successively. The reaction solution was heated to 60 C. and stirred for 2 hours. The reaction solution was concentrated under reduced pressure, mixed with 20 mL of water, stirred uniformly, and extracted with ethyl acetate (30 mL¡Á3). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound ethyl 1-((6-fluoroquinolin-4-yl)thio)cyclobutanecarboxylate 12c (100 mg, a yellow oil), yield: 59%.

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

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd; Jiangsu Hengrui Medicine Co.,Ltd.; Peng, Jian Biao; Sun, Pia Ohyang; Lan, Jiong; Koo, Cheon Yang; Lee, Siaotao; Liu, Bonnian; Han, Quanzhou; Hoo, Kwiye; Jean, Pang Pang; Dong, Qing; Cao, Guo Qing; (67 pag.)KR2016/6207; (2016); A;,
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