Month: March 2021

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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Related Products of 754125-43-4, The chemical industry reduces the impact on the environment during synthesis 754125-43-4, name is Methyl 3-(cyclopentylamino)propanoate, I believe this compound will play a more active role in future production and life.

To a stirred solution of methyl 3-(cyclopentylamino)propanoate (6.0 g, 35.0 mmol) and potassium carbonate (7.3 g, 52.6 mmol) in 150 mL of acetone was slowly added 2,4-dichloro-5-nitropyrimidine (6.8 g, 35.0 mmol, dissolved in 50 mL acetone) at 0 “C. The reaction mixture was stirred and allowed to approach room temperature over a period of 12-16 hours. After the reaction was complete as monitored by reverse phase analytical liquid-chromatography electrospray mass spectrometry (LC-MS), the solvent was removed in vacuo. The resulting slurry was then diluted in water and brine and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica- gel chromatography with dichloromethane:methanol (100:1 v/v) to give the title compound I-l-a (8.0 g, 69percent), MS (ESI) m/z 329 (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, Methyl 3-(cyclopentylamino)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DANA FARBER CANCER INSTITUTE; GRAY, Nathanael, S.; DENG, Xianming; KWIATKOWSKI, Nicholas, Paul; WO2010/80712; (2010); A2;,
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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;,
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Electric Literature of 680-65-9, 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. 680-65-9, name is Diethyl difluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 152. Preparation of 4-((lR,3aS,5aR,5bR,7aR,llaS,llbR,13aR,13bR)-3a ((3-(2-(dimethylamino)ethylamino)-2,2-difluoro-3-oxopropanamido)methyl)- 5a,5b,8,8, 11 a-pentamethyl- 1 -(prop- 1 -en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,ll,lla,llb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acid. Step 1: Preparation of the C28 reversed amide To a solution of tert-butyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- (aminomethyl)-5a,5b,8,8, 11 a-pentamethyl-1 -(prop- 1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate (200 mg, 0.333 mmol) in methanol (5 ml) and 1,4-dioxane (5 ml) was added diethyl 2,2-difluoromalonate (654 mg, 3.33 mmol). The resulting solution was stirred at rt for 6 days. The reaction mixture was concentrated in vacuo. The crude product was purified by Biotage (Thomson 25 g silica gel column; 4: 1 Hex/EtOAc) to give 116 mg (47 %) of product. MS: m/e 736.6 (MH+), 2.86 min (method 2). ? NMR (400 MHz, CHLOROFORM-d) delta ppm 0.93 (s, 6 H) 0.99 (s, 3 H) 1.02 (s, 3 H) 1.13 (s, 3 H) 1.60 (s, 9 H) 1.71 (s, 3 H) 0.85 – 1.83 (20 H) 1.98 – 2.10 (m, 1 H) 2.10 (dd, J=17.07, 6.27 Hz, 1 H) 2.49 (td, J=l 1.04, 5.27 Hz, 1 H) 3.16 (dd, J=13.55, 6.27 Hz, 1 H) 3.65 (dd, J=14.43, 7.15 Hz, 1 H) 3.95 (s, 3 H) 4.61 – 4.65 (m, 1 H) 4.73 (d, J=1.76 Hz, 1 H) 5.28 (dd, J=6.15, 1.63 Hz, 1 H) 6.28 (t, J=7.03 Hz, 1 H) 7.18 (d, J=8.53 Hz, 2 H) 7.89 (d, J=8.28 Hz, 2 H). iyF NMR (376 MHz, CHLOROFORM-d) delta ppm -112.49 (s, 2 F).

The chemical industry reduces the impact on the environment during synthesis Diethyl difluoromalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; SWIDORSKI, Jacob; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; MEANWELL, Nicholas A.; LIU, Zheng; WO2012/106188; (2012); A1;,
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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 17205-02-6 as follows. HPLC of Formula: C7H12O3

3-hydroxy-cyclobutane-carboxylic acid ethyl (800 mg)In tetrahydrofuran (25mL) solution,Reference Example 2-53 (1) synthesized in 2-chloro-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (4.24 g),Triphenylphosphine (5.68g),Toluene solution of diethyl azodicarboxylate (2.2M, 9.84mL) was added,It was stirred at room temperature for 13 hours. The temperature was raised to 60 , and the mixture was stirred for 7 hours at the same temperature.The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 100: 0 ? 70: 30) in the purified twice, to give the title compound (3.63g) as a colorless solid .

According to the analysis of related databases, 17205-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
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Adding a certain compound to certain chemical reactions, such as: 57486-68-7, name is Methyl 2-chlorophenylacetate, 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 57486-68-7, COA of Formula: C9H9ClO2

66.5 g (0.36 mol) of methyl o-chlorophenylacetate (III), 80 mL of tetrahydrofuran, and 8.9 g (0.37 mol) of sodium hydride were weighed.After stirring and dissolving, sodium hydride was completely dissolved, and then methyl 1-chlorocyclopropane-1-carboxylate 50 g (0.36 mol) was slowly added.Warm up to reflux, keep warm for 4h, gas phase tracking 1-chloro-1-carboxylic acid methyl ester-cyclopropane conversion rate of 99% or more, cooling to 20 ~ 25 C,The reaction solution was quenched by adding 60 mL of a 10% dilute hydrochloric acid solution, and 3.2 g (0.1 mol) of tetrabutyl bromide was added.The temperature is refluxed, the temperature is kept for 5 hours, the temperature is lowered to 20 to 25 C, and the organic phase is separated.The aqueous phase (50 mL x 2), extract the aqueous phase, and combine the organic phases.Desolventizing have to compound IV, as a pale yellow liquid 68g, 96% yield.

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; Anhui Jiuyi Agricultural Co., Ltd.; Shen Yunhe; Xiong Guoyin; Yu Zhenglian; Zhao Xiaojun; Zhou Quanquan; Fan Fuyun; (12 pag.)CN109369549; (2019); A;,
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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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These common heterocyclic compound, 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, 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. SDS of cas: 56741-34-5

Dissolve intermediate 1b (0.36g, 1.26mmol) in acetone solution,The reactants 1c (214 mg, 1.26 mmol) and pyridine (0.254 ml, 3.16 mmol) were added sequentially.Then, the reaction solution was heated to reflux at 60 degrees for 2h, and the reaction was monitored by mass spectrometry.The reaction solution was spin-dried and dissolved in ethyl acetate, washed with 1M hydrochloric acid solution in turn,After washing with saturated sodium chloride and drying over anhydrous sodium sulfate, the crude intermediate 1d was obtained.1d crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 5 / 1-2 / 1) to obtain 1d pure product (330mg, yield 62.5%),

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

Reference:
Patent; Fudan University; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; He Yulong; Wang Heyao; Li Yingxia; Dou Huixia; (68 pag.)CN110903224; (2020); A;,
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Reference of 36692-49-6, 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl (4-fluorophenyl)(oxo)acetate (50.0 g, 275 mmol) and methyl 3,4- diaminobenzoate (46.9 g, 282 mmol) in ethanol (2.5 L) was heated to reflux for 2 d. The mixture was cooled to rt and most of the ethanol was removed in vacuo to form a thick paste. 0.5 L of THF was added to get a stirrable slurry and the slurry was stirred for 1 h, diluted further with 1 L of ether and solid was collected by filtration (50.0 g, 76.3%) as a mixture of regioisomers.To a solution of methyl 2-(4-fluorophenyl)-3-oxo-3,4-dihydroquinoxaline-6-carboxylate(50.0 g, 168 mmol) (mixture of regioisomers) in THF (0.9 L) and methanol (0.9 L) at rt was added 2.0 M of sodium hydroxide in water (300 mL). The reaction mixture was stirred at 70 C for 2 h. The mixture was allowed to cool slightly and some solids formed. The reaction mixture was filtered while warm to afford a clear orange solution. The filtrate was stirred with mechanic stirring. IN HC1 aqueous solution (~ 450 rtiL) was slowly added (over 15 min) to pH=8. The suspension was stirred for 5 min, filtered, washed with 100 mL of 1:1 MeOH:THF, dried to give a light yellow solid. [In some cases, there is still some undesired isomer present at this point. If so, the material was redissolved in methanol/THF mixture (14 mL per gram of each solvent) and 1 N NaOH (4.2 equivalents), and then reprecipitated to pH = 8 using 1 N HC1. This dissolution/reprecipitation procedure can be repeated until the pure desired regioisomer is obtained.] To the solid was added 300 mL of methanol, 300 mL of THF, and 250 mL of IN NaOH and the resulting solution was stirred by mechanical stirring until dissolved. The resulting solution was adjusted to pH=2.5 by adding IN HC1. The precipitate was collected by filtration, transferred to a round bottom flask using MeOH, evaporated in vacuo, and azeotroped with MeCN. The resulting solid was dried in vacuum pump to give a pure acid product (26.3 g, 55.2%) as a beige powder. LCMS (ESI+): m/z = 285.0 (M+H). H NMR (400 MHz, DMSO-6) delta 13.34 (s, 1H), 12.76 (s, 1H), 8.44 (dd, J= 9.1, 5.8 Hz, 2H), 7.96 – 7.89 (m, 2H), 7.83 (dd, J= 8.4, 1.8 Hz, 1H), 7.35 (t, J= 9.0 Hz, 2H).

The synthetic route of Methyl 3,4-diaminobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; GIGSTAD, Kenneth, M.; CARDIN, David, P.; HIRAYAMA, Takaharu; HIROSE, Masaaki; HU, Yongbo; KAKEI, Hiroyuki; LEE, Hong, Myung; MOTOYAJI, Takashi; NII, Noriyuki; SHI, Zhan; VYSKOCIL, Stepan; WATANABE, Hiroyuki; WO2015/161142; (2015); A1;,
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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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