Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 29006-01-7, name is Methyl 4-methoxybutanoate, 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 29006-01-7, Computed Properties of C6H12O3

To a stirred, cooled (-78 C.) solution of 1.32 g (10.0 mmol) of methyl 4-methoxybutanoate in 15 mL of anhydrous THF under an atmosphere of nitrogen was added 10.5 mL (10.5 mmol) of a 1.0 M solution of LiHMDS in tetrahydrofuran. The resulting mixture was stirred for 1 h, then 1.09 g (10 mmol) of chlorotrimethylsilane was added. After stirring for 20 min, 1.78 g (10.0 mmol) of solid N-bromosuccinimide was added and the mixture was stirred for 2 h at -78 C., then slowly warmed to ambient temperature over 40 min. The reaction was quenched with a saturated aqueous ammonium chloride solution and then the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The crude residue was dissolved in 15 mL of DMF and 5.5 g (40 mmol) of potassium carbonate followed by 3.4 g (50 mmol) of 1H-pyrazole were added. The resulting mixture was heated to 80 C. for 40 min, then cooled to ambient temperature. The reaction was diluted with 75 mL of water and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The crude residue was purified by reverse phase HPLC (TMC Pro-Pac C18; 0-75% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to yield the title compound (0.26 g, 13%). LC-MS: m/z (ES) 199 (MH)+.

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Reference:
Patent; Berger, Richard; Chang, Lehua; Edmondson, Scott D.; Goble, Stephen D.; Ha, Sookhee Nicole; Kar, Nam Fung; Kopka, Ihor E.; Li, Bing; Morriello, Gregori J.; Moyes, Chris R.; Shen, Dong-Ming; Wang, Liping; Zhu, Cheng; US2009/253705; (2009); A1;,
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Electric Literature of 15568-85-1, A common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C8H10O5, 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 3[00178] To a stirred solution of the l-(3,4-dichloro-phenyl)-ethanone oxime (1 eq) in dry THF (6vol) cooled externally to -15C was added 2.5M n-BuLi (2.2 eq) dropwise. After stirring the reaction mixture for 75 minutes, 5-methoxymethylene- 2,2-dimethyl-[l,3]dioxane-4,6-dione (1.0 eq) in THF (9 vol) was added to the externally cooled reaction mixture. After 1 hour the reaction mixture was warmed to 0C for 15 minutes, and then stirred for 16 hours at room temperature. The reaction mixture was added to water (27vol) and extracted with TBME (2 x 7vol). The aqueous layer was acidified with 5M H2SO4 (3vol) and further extracted with TMBE (3 x 7 vol). The combined organics were filtered and concentrated under reduced pressure to give a crude residue.

The synthetic route of 15568-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHDI, INC.; WITYAK, John; TOLEDO-SHERMAN, Leticia, M.; LEEDS, Janet; DOMINGUEZ, Celia; COURTNEY, Stephen, Martin; YARNOLD, Christopher, John; DE AGUIAR PENA, Paula, Cristina; SCHEEL, Andreas; WINKLER, Dirk; WO2010/17132; (2010); 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. 61644-18-6, name is Chloromethyl isobutyrate, A new synthetic method of this compound is introduced below., Computed Properties of C5H9ClO2

General procedure: Carboxylic acid (±)-9 (5.18 mmol) was dissolved in N,N-dimethylformamide (15.5 mL). Cesium carbonate (4.14 mmol) was added to the solution and the suspension was stirred during 2-3 min after which chloromethyl 2-methylpropanoate (6.73 mmol) was added. After stirring at room temperature during 18-24 h, dichloromethane (30 mL) was added to the mixture and the resulting organic phase was successively washed with water (3×20 mL) and brine (3×20 mL). Organic solvent was eliminated and the residue was submitted to flash chromatography (hexane/ethyl acetate mixtures) to yield the corresponding diester (±)-5.

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:
Article; Torres, Susana Y.; Ochoa, Estael; Verdecia, Yamila; Rebolledo, Francisca; Tetrahedron; vol. 70; 31; (2014); p. 4675 – 4684;,
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Electric Literature of 42726-73-8,Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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: alpha-Monosubstituted malonic diester 1 was synthesized according to the reported procedure as follows.3 tert-Butyl methyl malonate was purchased from Kanto Chemical, and used without further purification. The physical properties and spectral data of the new compounds, 2-(2-methylbenzyl)malonate 1g, 2-prenylmalonate 1l, and 2-(2-benzyloxyethyl)malonate 1o, are listed below. A 100 mL round-bottom flask equipped with a stirring bar was charged with tert-butyl methyl malonate (846 muL, 5.0 mmol) and DMF (10 mL). To the solution, sodium hydride (60percent oil suspension, 200 mg, 5.0 mmol) was added. The reaction was allowed to stir at 0 °C for 30 min. To the mixture, corresponding alkyl halide (5.0 mmol) was added at 0 °C and the mixture was stirred at room temperature for 24 h. To the reaction mixture, H2O was added, and the mixture was extracted with CH2Cl2 (3 * 20 mL), dried over MgSO4, and concentrated in vacuo. The remaining residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the desired product 1.

The synthetic route of 42726-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Odanaka, Yuki; Kanemitsu, Takuya; Iwasaki, Kanako; Mochizuki, Yukiko; Miyazaki, Michiko; Nagata, Kazuhiro; Kato, Masaru; Itoh, Takashi; Tetrahedron; vol. 75; 2; (2019); p. 209 – 219;,
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Electric Literature of 4224-69-5, 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 4224-69-5 as follows.

To a dry nitrogen-flushed 15 mL round bottom flask was added dry THF (5.9 mL) and iPr2NH(0.87 mL, 6.21 mmol, 1.05eq.). The flask was cooled to -78 C andn-BuLi(2.48 mL, 6.21 mmol, 1.05eq.) was added slowly. The mixture wasstirred at 0 C for 10 minutes and then cooled back down to -78 C and cannulated into a -78 C solution of starting material(1.16 g, 5.91 mmol, 1.00eq.) in THF (5.9 mL).The reaction mixture was stirred for 30 min at -78 C and then methyl(2-bromomethyl)acrylate wasadded (0.87 mL, 7.09 mmol,1.20 eq.) via syringe. The reaction wasstirred for 1h at -78 C then 3 h at r.t. The reaction was quenched with H2O(10 mL) and extracted with Et2O (2 x 20 mL). The combinedorganics were washed with brine (10 mL), dried withMgSO4, rotovapped, and chromatographedto yield the desired product was a white solid (1.5338 g, 5.21 mmol) in 88% yield. 1H NMR (300 MHz, CDCl3)delta 8.03 – 7.91 (m, 2H), 7.47-7.38 (m, 1H), 7.36 – 7.13 (m, 7H), 6.07 (s,1H), 5.41 (s, 1H), 4.95 (t, J = 7.2Hz, 1H), 3.71 (s, 3H), 3.23 (dd, J = 14.1, 7.3 Hz, 1H), 2.79 (dd, J = 14.0, 7.2 Hz, 1H).. 13C NMR (75 MHz, CDCl3) delta 198.7, 167.2, 138.7,137.3, 136.5, 132.8, 128.8, 128.6, 128.4, 128.2, 128.0, 127.9, 127.1, 52.2,51.8, 36.7.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ramachandran, P. Veeraraghavan; Helppi, Matthew A.; Lehmkuhler, Arlie L.; Marchi, Jennifer M.; Schmidt, C. Max; Yip-Schneider, Michele T.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 19; (2015); p. 4270 – 4273;,
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Reference of 23680-40-2,Some common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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.

Intermediate 142Cmethyl 2-bromo-5-(diisopentylcarbamoyl)pyrazolo[1 ,5-a]pyridine-3-carboxylateA suspension of /V-aminopyridinium 2,4-(dinitro)phenolate (10 g, 21.67 mmol), methyl 3- bromopropiolate (3.12 ml, 26.0 mmol) and potassium carbonate (5.99 g, 43.3 mmol) in degassed DMF (75 ml) was stirred at 0 C for 5 minutes and at 22 C for 18h. The mixture was diluted with ethyl acetate (100 mL) and washed with water (3 x 25 mL), brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (120g, 0% to 100% ethyl acetate/hexanes over 19 min). to provide methyl 2-bromo-5-(diisopentylcarbamoyl)pyrazolo[1 ,5- a]pyridine-3-carboxylate (0.52 g, 1.186 mmol, 5.47 % yield). LCMS m/z 438.4, 440.1 (M + H)+.

The synthetic route of 23680-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; BOUVIER, Michel; MARINIER, Anne; RUEL, Rejean; RENE , Patricia; CHANTIGNY, Yves; DAGNEAU, Philippe; GINGRAS, Stephane; WO2012/100342; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 403-33-8, name is Methyl 4-fluorobenzoate, 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 403-33-8, Recommanded Product: 403-33-8

General procedure: Hydrazine hydrate (5 mL, 40%) was added to a solution of requiredester (5.0 mmol) in methanol (20 mL). The solution was refluxed for12-24 h and monitored by TLC until starting material was completelyconsumed. After that, solvent was evaporated under reduced pressureand a small amount of water (5 mL) was added to precipitate the hydrazide,which was filtered and dried in vacuum to give a shiny white toyellow solid in excellent yields, without further purification.

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Reference:
Article; Chen, Lixia; Gao, Suyu; Li, Hua; Li, Mingxue; Li, Xingzhou; Liu, Yang; Wu, Canrong; Yang, Kaiyin; Zhang, Yujie; Zheng, Mengzhu; Bioorganic Chemistry; vol. 96; (2020);,
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Electric Literature of 606-45-1, 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. 606-45-1, name is Methyl 2-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of esters (2a~2t, 1.0 equiv.), furan-2-carbonyl chloride (7a, 1.0 equiv.) orthiophene-2-carbonyl chloride (7b, 1.0 equiv.) in MeOH (2 mL/1 mmol) was added hydrazine hydrate(1 mL/1 mmol), then the mixture was allowed to reach 65 C and stirred for 4 h. After completion(monitored by TLC), the organic solvent was removed and extracted three times with ethyl acetate,the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to givethe corresponding hydrazides (3a~3t, 8a, or 8b) in high yields, which were taken up for the next stepwithout any purification.

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

Reference:
Article; Yuan, Chen; Yan, Jie; Song, Chen; Yang, Fan; Li, Chao; Wang, Cheng; Su, Huiling; Chen, Wei; Wang, Lijiao; Wang, Zhouyu; Qian, Shan; Yang, Lingling; Molecules; vol. 25; 1; (2020);,
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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. 35180-01-9, name is Chloromethyl isopropyl carbonate, A new synthetic method of this compound is introduced below., name: Chloromethyl isopropyl carbonate

A method for synthesizing tenofovir disoproxil, in a dry and clean 1000 mL three-neck reaction flask with mechanical stirring, after nitrogen substitution, 500 mL of N, N-dimethylacetamide was added at room temperature, and tenofovir (PMPA ) 86.1g (0.3 mol, 1.0 equiv), triethylamine 60.6g (0.6 mol, 2.0 equiv), tetrabutylammonium bromide 9.7g (0.03 mol, 0.1 equiv), urea 18.2g (0.3 mol, 1.0 equiv) After stirring for 30min, the temperature was raised to 50 ~ 60 C, and 137.2g (0.9mol, 3 equiv) of POC was slowly added dropwise. After the dropwise addition was completed, the reaction was continued for about 3 hours. After the temperature was lowered, the reaction solution was flushed into 2000mL of ice brine, and stirred Hours, filtered to obtain crude tenofovir dipyrfurate, then beaten once with 300 ml of isopropyl acetate, filtered, and dried to obtain 127.8 g of tenofovir dipyrfurate, purity 98.5%, yield 82.0%.

The synthetic route of 35180-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aoruite Pharmaceutical Co., Ltd.; Xu Tingjun; Xie Xiaoqiang; Liu Xijing; Zhou Tianxi; Xu Xiaobo; (7 pag.)CN110590842; (2019); A;,
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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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

Step c) 4-[(Biphenyl-2-carbonyl)-amino]-2-methoxybenzoic acid methyl ester Into a refluxing solution of 2-biphenylcarboxylic acid (9.2 g, 46 mmol) in dichloromethane was added dimethylformamide (0.1 ml, 1.4 mmol) and then neat oxalyl chloride (8.1 ml, 92 mmol) via syringe. The reaction was refluxed for 10 min, then the volatiles removed in vacuo. The residue was redissolved in dichloromethane, concentrated and dried under high vacuum for 15 min. The acid chloride was dissolved in dichloromethane (50 ml) and added into a 0° C. solution of 4-amino-2-methoxy-benzoic acid methyl ester (8.4 g, 46 mmol), diisopropyl ethylamine (10.5 ml, 60 mmol) and dichloromethane (200 ml). The reaction was warmed to room temperature and stirred for 16 hours. The reaction was diluted with dichloromethane, washed with water, (1N) sodium hydroxide (1N) HCl and brine, and dried (MgSO4). Evaporation gave a yellow foam, which was crystallized from methanol to give a light yellow solid (16.08 g, 96percent) m.p. 141°-142° C. Analysis for: C22 H19 N O4 Calcd: C, 73.12; H, 5.30; N, 3.88. Found: C, 72.93; H, 5.20; N, 3.83.

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

Reference:
Patent; American Cyanamid Company; US5753648; (1998); A;,
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