Tag: M.W=100-200

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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-amino-3-fluorobenzoate

Example 38A Methyl 4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}-3-fluorobenzoate (0496) (0497) 1.00 g (2.55 mmol) of the compound from example 2A were dissolved in 10 ml of 49 DMF. To the solution were added 474 mg (2.80 mmol) of 158 methyl 4-amino-3-fluorobenzoate and 429 mg (3.82 mmol) of 153 potassium tert-butoxide. The reaction mixture was stirred at RT for 1 h and then stirred into a mixture of 50 ml of 44 ice-water, 50 ml of 159 ammonium chloride solution and 100 ml of 61 ethyl acetate. The organic phase was removed, washed twice with water and once with saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by means of column chromatography (silica gel, eluent: 5% ethyl acetate/95% cyclohexane?15% ethyl acetate/85% cyclohexane?45% ethyl acetate/55% 160 cyclohexane, Biotage). The product-containing fractions were concentrated and the residue was stirred in 10 ml of 45 tert-butyl methyl ether. The solids were filtered off, washed twice with 5 ml of tert-butyl methyl ether and then stirred in 4 ml of ethyl acetate for three days. The solids were then filtered off again and dried under reduced pressure. 810 mg (64% of theory, 99% purity) of the 161 title compound were obtained. (0498) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=11.10 (s, 1H), 8.27 (t, 1H), 8.05 (d, 1H), 7.99 (d, 1H), 7.95-7.90 (m, 2H), 7.85 (dd, 1H), 7.64-7.62 (m, 2H), 7.58-7.51 (m, 3H), 3.89 (s, 3H), 2.43 (s, 3H). (0499) LC/MS (Method 1, ESIpos): Rt=1.27 min, m/z=493/495 [M+H]+.

The synthetic route of 185629-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesekkschaft; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEIBOM, Daniel; MEININGHAUS, Mark; TERJUNG, Carsten; DELBECK, Martina; LUSTIG, Klemens; MUENSTER, Uwe; OLENIK, Britta; (100 pag.)US2017/260140; (2017); A1;,
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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. Safety of Methyl 4-amino-2-methoxybenzoate

(2) the above-mentioned the resulting 4-amino-2-methoxybenzoic acid methyl ester and N-chloro succinimide the mole ratio is that 1:1 in 70 C stirring in DMF solution of 3 hours later, is poured into the ice water is separated out in solid, filtering and drying to obtain 1.70 kg of 4-amino-5-chloro-2-methoxybenzoic acid methyl ester, in the yield of 88.3%.

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

Reference:
Patent; Nanjing University of Science and Technology; Ma, Kefeng; Ren, Yu; Pan, Xiongfei; Wu, Jiating; Xu, Tongqiang; (6 pag.)CN105237422; (2016); A;,
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Application of 14062-18-1, 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 14062-18-1 as follows.

p-Methoxy toluene (1.83 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120 C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl p-methoxyphenylacetate was obtained by column chromatography, in a yield of 85%. 1HNMR (400 MHz, CDCl3) delta 1.23 (t, J=6.8 Hz, 3H), 3.54 (s, 2H), 3.79 (s, 3H), 4.11 (q, J=6.8 Hz, 2H), 6.84-6.88 (m, 2H), 7.18-7.22 (m, 2H); 13CNMR (100 MHz, CDCl3) delta 14.2, 40.5, 55.3, 60.8, 113.9, 126.3, 130.3, 158.7, 171.9; HRMS (ESI) calcd. for C11H14NaO3 [M+Na]: 217.0835. found: 217.0838. The ethyl p-methoxyphenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60 C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 64 mg product p-methoxyphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.

According to the analysis of related databases, 14062-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); A1;,
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Related Products of 66315-16-0,Some common heterocyclic compound, 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, molecular formula is C9H12N2O2, 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.

800 mg (4.4 mmol) s3 was dissolved in 10 mLacetic acid, 336 mg (4.8 mmol) sodium nitrite was added slowly.The mixture was stirred for 18 h at room temperature, then poured into 30 mL water, neutralized with saturated solution of sodium bicarbonate, extracted with 50 mL ethyl acetate, washed with 20 mL water, dried with anhydrous sodium sulfate overnight. The filtrate was concentrated by vacuum distillation to obtain brown solid, recrystallized from ethyl acetate and hexane to afford pale brown solid of s4 300 mg, yield 35%.1H NMR(400 MHz, CDCl3): d8.78 (s, 1H, ArH), 8.19 (d, 1H, J = 8.8 Hz, ArH), 7.55 (d, 1H, J = 8.8 Hz, ArH), 4.33 (s, 3H, OCH3), 3.98 (s, 3H, NCH 3 );13C NMR (100 MHz,CDCl3): d 166.6, 145.6, 135.6, 128.2, 126.3, 122.9, 109.0, 52.4, 34.4.HRMS (EI) calcd. for C9H9N3O2 [M]+: 191.0695, found 191.0697.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-4-(methylamino)benzoate, its application will become more common.

Reference:
Article; Chang, Kang; Chen, Jian-Qin; Shi, Yan-Xia; Sun, Mei-Jian; Li, Peng-Fei; Zhao, Zhen-Jiang; Zhu, Wei-Ping; Li, Hong-Lin; Xu, Yu-Fang; Li, Bao-Ju; Qian, Xu-Hong; Chinese Chemical Letters; vol. 28; 4; (2017); p. 919 – 926;,
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Synthetic Route of 680-65-9, A common heterocyclic compound, 680-65-9, name is Diethyl difluoromalonate, molecular formula is C7H10F2O4, 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.

Step 1: 2,2-difluoropropane-1,3-diol To a solution of diethyl difluoromalonate (3.77 g, 19.22 mmol) in THF (19.22 ml) at 0 C., was added Lithium Aluminium Hydride (1M in THF, 30.8 ml, 30.8 mmol) drop-wise. The reaction mixture was brought to ambient temperature and then stirred for 16 hours. The reaction mixture was then slowly poured onto an ice-cold suspension of 4 g of Na2SO4.10H2O in 20 mL of THF. This was stirred for 1 h and the resulting slurry was filtered, rinsed with 1:3 MeOH/EtOAc. The filtrate was collected and concentrated to give the title compound (1.7 g, 15.17 mmol, 79% yield) as a white paste.

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; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
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Application of 5048-82-8, 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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 7; Ethyl (2E)-3 (4-{ [(1-aminocyclopentyl)carbonyl]amino}phenyl)acrylate; 1-{[benzyloxy)carbonyl]amino}cyclopen(anecarboxylic acid was dissolved in DMF (0.2 M). HATU (1 eq.) and triethylamine (3 eq.) were added, followed by ethyl cinnamate (0.95 eq.). The resulting mixture was stirred for 48 h at 40 °C. DMF was evaporated, the resulting oil taken up in EtOAc and the solution washed with HQ (3x, 1 M), water, a solution of saturated aqueous NaHC03 (2x) and brine. Drying over Na2SO4 and evaporation gave an orange solid, which was purified by flash chromatography on silica gel using PE/EtOAc (2.5 : 1. containing 1percent EtOH) as the eluent The resulting solid was immediately dissolved in DCM (0,1 M) and triflic acid (5 eq.) was added dropwise at RT, After 5 mm at RT, the red mixture was poured into an aqueous solution of NaHCOj. The organic phase was separated, the aqueous phase was extracted with DCM (4x) and the combined organic phases dried over Na2SO4. Evaporation gave the title compound as an off-white solid, which was used without further purification.

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

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2006/29912; (2006); A1;,
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Synthetic Route of 110104-60-4,Some common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, molecular formula is C6H9ClO3, 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 a mixture of 4-phenoxyaniline (10 g) and acetonitrile (40 mL) was added a mixture of methyl 4-chloro-3-methoxy-2-(E)-butenoate (9.18 mL) and acetonitrile (40 mL) at 0 C. To the reaction mixture was added a mixture of triethylamine (8.28 mL) and acetonitrile (20 mL) at 0 C. The reaction mixture was heated under reflux for 4 hr and cooled to room temperature. The precipitate was removed by filtration. To the filtrate was added water (80 mL), and the mixture was adjusted to pH 3 with concentrated hydrochloric acid. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. To the residue were added toluene (80 mL) and acetic acid (2.0 mL) at room temperature. The reaction mixture was heated at 50 C. for 1.5 hr. The reaction mixture was diluted at room temperature with water, saturated brine and saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (7.43 g). MS: [M+H]+ 281.8.

The synthetic route of 110104-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOIKE, Tatsuki; FUSHIMI, Makoto; AIDA, Jumpei; IKEDA, Shuhei; KUSUMOTO, Tomokazu; SUGIYAMA, Hideyuki; TOKUHARA, Hidekazu; (170 pag.)US2016/318864; (2016); A1;,
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Synthetic Route of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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.

The compound 2,4-difluorobenzoic acid (950 mg, 6 mmol) was dissolved in 2 ml of thionyl chloride,Heated to 80 C reflux2 hours,After completion of the reaction, the solvent was dried to give an oily compound,The oily compound was placed on an oil pump for half an hour,Immediately put the next step.The compound of the previous step was quickly dissolved in dry toluene,And ethyl 3- (dimethylamino) acrylate (1 g, 7 mmol) was added,Triethylamine (1.01 g, 10 mmol)Heated to 90 C,Fully stirred for 12h,Cooled to room temperature, spin dry solvent, dissolved in ethyl acetate and washed several times with water,After concentration, the compound 1a (1.42 g, 85%) was obtained as a yellow oil by column chromatography elution (petroleum ether: ethyl acetate = 10: 1 to 2: 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-(dimethylamino)acrylate, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Geng Meiyu; Li Bowen; Ai Jing; Xu Zhongliang; (65 pag.)CN107151240; (2017); A;,
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Electric Literature of 89-91-8,Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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.

j00399j A mixture of(3,4-difluorophenyl) methanamine (2.0 g, 14 mmol) and methyl 2,2- dimethoxyacetate (3.8 g, 28 mmol) was stirred at 140 C for 1 hour in the microwave. On completion, the reaction mixture was diluted with dichloromethane (20 mL) and concentrated in vacuo to give cmde compound B-64 (4.3 g, crude) as a yellow solid. LCMS (E): tR=0.596 mi, (ES) mlz (M+H) =246.1.

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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Related Products of 4891-38-7, 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 4891-38-7 as follows.

General procedure: A 25 mL Schlenk tube equipped with a magnetic stirringbar was charged with I2 (12.7 mg, 0.05 mmol), substituted thiol1 (0.5 mmol) and alkyne 2 (0.75 mmol). The tube was evacuatedtwice and backfilled with nitrogen, and DTBP (2.5 mmol)was added into the tube under nitrogen atmosphere. The tubewas sealed with a balloon and the mixture was stirred undernitrogen atmosphere at 110 C for 18 h. Upon completion of thereaction, the resulting solution was cooled to r.t., and thesolvent was removed with the aid of a rotary evaporator. Theresidue was purified by column chromatography on silica gel(PE-EtOAc) to give 3.

According to the analysis of related databases, 4891-38-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yan, Kelu; Yang, Daoshan; Zhang, Mengqi; Wei, Wei; Liu, Yao; Tian, Laijin; Wang, Hua; Synlett; vol. 26; 13; (2015); p. 1890 – 1894;,
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