Author: Jessica.F

Application of 69812-51-7, 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 69812-51-7 as follows.

General procedure: To a solution of compound 7 (400mg, 1.0 eq) in CH2Cl2 or MeCN (30mL), the substituted benzenesulfonyl chloride (1.2 eq), K2CO3 (3.5 eq) were added and stirred at room temperature overnight. After reaction completed, the solvent was removed under reduced pressure and the residue was dissolved with ethyl acetate, washed by brine, dried, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluents and then acidized with 2N HCl/Et2O (1mL) to give the title compounds (8a-h).

According to the analysis of related databases, 69812-51-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cheng, Xin-Yue; Li, Yu-Huan; Tang, Sheng; Zhang, Xin; Wang, Yan-Xiang; Wang, Sheng-Gang; Jiang, Jian-Dong; Li, Ying-Hong; Song, Dan-Qing; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 133 – 142;,
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Related Products of 54335-33-0, These common heterocyclic compound, 54335-33-0, name is Methyl 2,4-dibromobenzoate, 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: To a solution of benzoic acid methyl ester (3, 4a,b) (500 mg), the respective arylamine compounds (2.4 equiv for 3, 1.2 equiv for 4a,b), Cs2CO3 (2.8 equiv for 3, 1.4 equiv for 4a,b), BINAP (0.08 equiv) in 1,4-dioxane (5 mL) was added Pd(OAc)2 (5 mol percent) under nitrogen. And the reaction mixture was stirred at 100 °C for 10?24 h. The reaction mixture was cooled to room temperature, and then H2O was added. The mixture was extracted with ethyl acetate, and then the organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography.

The synthetic route of 54335-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Chao; Lin, Kai; Huang, Lan; Pan, Wei-Dong; Liu, Sheng; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2490 – 2494;,
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Synthetic Route of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, 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.

A 2.5 M solution of n-BuLi in hexane (2.04 mL, 5.10 mmol, 1.02 equiv) is added dropwise to a solution of diisopropylamine (0.74 mL, 5.25 mmol,1.05 equiv) in anhydrous THF (5 mL) at -78 C under Ar atmosphere and thereaction mixture is allowed to stir for 30 min at -78 C. After stirring an additional 30 min at -5 C, a solution of methyl 2,2-diphenylacetate (1.13 g, 5.00 mmol,1.00 equiv) in anhydrous THF (2 mL) is added dropwise at -78 C, and the reaction mixture is allowed to stir for 10 min. Finally, crotyl bromide (trans, 85% pure; 810 mg,6.00 mmol, 1.20 equiv) is added dropwise at -78 C and the mixture is slowly warmed to rt. After stirring for 16 h at rt, the reaction mixture is cooled to 0 C, quenched by the addition of saturated aq. NH4Cl (10 mL) then extracted with Et2O (4 × 10 mL). The combined organic extracts are washed with brine, dried overanhydrous Na2SO4, filtered and concentrated under reduced pressure; yield: 1.00 g, 3.57 mmol, 71%, yellow liquid. The product is obtained as inseparable mixture of E/Z isomers (90:10; cf. NMR spectra).

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

Reference:
Article; Rode, Katharina; Palomba, Martina; Ortgies, Stefan; Rieger, Rene; Breder, Alexander; Synthesis; vol. 50; 19; (2018); p. 3875 – 3885;,
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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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H11NO3

A mixture of l -amino-3-[tert-butyl (dimethyl) silyl] oxy-5-cyclopropyl-pyrrolidin-2-one (10.5 g, 38.83 mmol) and ethyl 2-ethoxy-2-imino-acetate (14.1 g, 97.06 mmol) in ethanol (150 mL) was stirred at 90 C for 12 h and concentrated under reduced pressure to afford crude ethyl 2-[[3-[tert- butyl (dimethyl) silyl] oxy-5-cyclopropyl-2-oxo-pyrrolidin-l-yl] amino]-2-imino-acetate (10.0 g, 70%) as a yellow oil. LCMS RT = 0.804 min, m/z =370.2 [M + H]+. LCMS (5 to 95% acetonitrile in water + 0.03%o trifluoacetic acid over 1.5 mins) retention time 0.804 min, ESI+ found [M+H] =370.2.

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 924-99-2

N-[2-methoxyl-4[4-(dimethyl amino)piperid-1-yl]aniline]guanidine (II) (2.9 g, 10 mmol), N,N-dimethylaminoethyl acrylate (2.0 g, 14.0 mmol) and N,N-dimethylformamide 30 mL were added in a reaction bottle, were heated to a temperature of 115-125 C., and were subjected to stirring reaction for 22-24 hours to finish TLC detection reaction. Concentration under reduced pressure was carried out, obtained residues were added with 50 mL of ethanol, and were cooled to room temperature while stirring, and then solid was separated out. The solid was filtered, a filter cake was washed with cold ethanol, and was dried under vacuum to obtain off-white solid N2-[4-[4-(dimethyl amino)-1-piperidyl]-2-methoxyphenyl]amino-4(1H)-pyrimidone (III) 2.73 g, the yield was 79.6%, and FAB-MS m/z: 344 [M+H]+.

According to the analysis of related databases, 924-99-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUZHOU MIRACPHARMA TECHNOLOGY CO., LTD.; Xu, Xuenong; (7 pag.)US10039775; (2018); B2;,
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Reference of 653-92-9, These common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-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.

Treat a solution of l-vinylpyrrolidin-2-one (2 g, 8.58 mmol) in dry THF (30 mL) with lithium diisopropylamide (LDA) (13 mL, 31.45 mmol) at -20 0C under N2 atmosphere and stir at the same temperature for 30 min. Then add methyl 2-bromo-4- fluorobenzoate (2 g, 8.58 mmol) and stir it over the weekend. Add an HCl (12 N, 9 mL) solution and water (12 mL). Remove the THF and add HCl (12 N, 12 mL) and water (15 mL). Heat it to 100 0C for 15 h. Cool the mixture to RT and add a 5 % NaOH solution. Extract the solution with ether, dry over magnesium sulfate, and remove the solvent. Purify the residue by column chromatography (hexane to ethyl acetate) to give the title compound (0.42 g, 27 %). MS (ES) m/z 244 [M+l]+.

The synthetic route of 653-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/144223; (2008); A2;,
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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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 10601-80-6

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL×3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
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Application of 1687-29-2, These common heterocyclic compound, 1687-29-2, name is Cis-dimethyl cyclohexane-1,2-dicarboxylate, 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.

SOCl2 (15.45 g, 129.8 mmol) was added to a mixture of cis-1,2-cyclohexanedicarboxylic anhydride (200 g, 1298 mmol) and methanol (1400 mL) at 20 °C.There ac-tion mass was refluxed for 3?4 h. Methanol was concentrated completely, the residue was diluted with methyl-tert-butyl ether(MTBE, 1000 mL), sodium bicarbonate solution was added to it. The organic layer was separated and washed with water and brine solution. The organic layer was distilled completely to furnish 8. The residue was dissolved in fresh methanol (1040 mL), and sodium methoxide (28 g, 519.4 mmol) was added. The reaction mass was refluxed for 4h, and methanol was distilled completely under reduced pressure. To the residue, 13percent aqueous NaOH solution (2000 mL)was added. Reaction mass was maintained for 3?4 h at 75 °C and cooled to 0?5 °C. The reaction mass pH was adjusted to 2.0 at 0?5 °C with concentrated HCl (900 mL). The obtained solid was filtered and the wet cake was washed with excess water (1500 mL) and dried under reduced pressure to give a white solid. Yield: 87percent. HRMS (ESI TOFMS): calcd. for C8H12O4Na, 173.0814; found, 173.0821. HPLC conditions: chemical column: Zorbax SB CN (150×4.6 mm)×(3.5mu); mobile phase: A: 0.1percent H3PO4 in H2O/MP; B: ACN, purity by HPLC (area under curve): 94.3percent; (trans) retention time: 6.98 and 2.1percent; (cis) retention time: 7.579. Chiral column: Chiral PAK IC (250×4.6 mm) 5.0 mum; mobile phase: n-hexane/IPA/TFA (950:50 l:1); diluent: methanol/MP (1:1); flow rate: 1.0 mL/min; column temperature: 25 °C; inj. vol.: 10 mul. Wave length: 210 nm. Purity by HPLC (area under curve) 40.35percent (R,S isomer), retention time 16.065; and 56.18percent (R,S isomer) retention time 20.269.

The synthetic route of 1687-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ravi Ganesh; Pachore, Sharad S.; Pratap; Umesh; Basaveswara Rao; Murthy; Suresh Babu; Synthetic Communications; vol. 45; 23; (2015); p. 2676 – 2682;,
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Related Products of 653-92-9, 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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : Triethylamine (13 mL, 9.44 g, 93.3 mmol), potassium isopropenyltrifluoroborate (18.0 g, 121 .6 mmol) and PdCl2(dppf).CH2Cl2 (1.38 g, 1.70 mmol) were added to a solution of compound 479 (21.8 g, 93.6 mmol) in n-propanol (640 mL) and the mixture was heated at reflux for 17 hours. TLC analysis (10% 2-butanone in heptane) showed starting material remaining and PdCl2(dppf).CH2Cl2 (0.69 g, 0.84 mmol) was added and heating continued for a further 4 hours. After cooling to room temperature the mixture was concentrated to -100 mL in vacuo and diluted with EtOAc (400 mL) before being washed with 1 M HCI (250 mL) and brine (250 mL). The combined aqueous washings were extracted with EtOAc (100 mL) and this was washed with brine (75 mL). The combined organic layers were dried (MgS04) and concentrated in vacuo to give a dark brown oil. Purification by column chromatography (1500 mL silica, 4% EtOAc in heptane) gave the desired product (8.63 g, 47%) as a colorless liquid, contaminated with methyl 4-fluorobenzoate (<10%), and a mixture of the desired product and starting material (5.05 g) also contaminated with methyl 4-fluorobenzoate. Further purification by column chromatography (500 mL silica, 4% EtOAc in heptane) gave a further 1.60 g (9%) of the desired product contaminated with methyl 4-fluorobenzoate (<10%). The product was further purified by Kugelrohr distillation, discarding the forerun (70C, 4 mmHg), and then increasing the temperature to 95C to collect the compound 480 (95% recovery) containing <5% methyl 4- fluorobenzoate. 1 H NMR (400 MHz, CDCI3) delta 7.84 (dd, J = 8.7, 5.9 Hz, 1 H) 6.99 (ddd, J = 8.6, 8.0, 2.6 Hz, 1 H) 6.93 (dd, J = 9.4, 2.6 Hz, 1 H) 5.12 (p, J = 1.6 Hz, 1 H) 4.85 (dq, J = 1.8, 0.9 Hz, 1 H) 3.85 (s, 3H) 2.07 (t, J = 1 .2 Hz, 3H). LCMS m/z 195 [M+H]+. The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-4-fluorobenzoate. I believe this compound will play a more active role in future production and life. Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); 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. 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;,
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