Author: Jessica.F

Synthetic Route of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of the amino-acetaldehyde diethyl acetal (13.16 g, 99 mmol) in ether (35 mL) is added to a suspension of CNBr (10.47 g, 99 mmol) in hexane (35 mL) at room temperature. The reaction mixture is stirred at room temperature overnight. The solid is removed by filtration and washed with ether. The combined filtrate is concentrated. Purification by column chromatography (silica gel, eluding with dichloromethane to 4% methanol in dichloromethane, gradient) affords N-(2,2-Diethoxyethyl)carbodiimide (Rf: 2.70, 4% methanol in dichloromethane, stain with 10% ethanolic molybdatophosphoric acid): 1H NMR 400 MHz (CDCl3) delta 4.58 (t, J=5.2 Hz, 1H), 3.77-3.69 (m, 2H), 3.65 (br, s, 1H), 3.60-3.52 (m, 2H), 3.16 (t, J=5.6 Hz, 1H), 1.23 (t, 6H, J=6.8 Hz).

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

Reference:
Patent; IRM LLC; US2008/188483; (2008); A1;,
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Application of 651734-54-2, 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. 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Chlorothieno[3,2-d]pyrimidine-7-carboxylic acid(23mg, O.lOmmol) prepaed in step g of Example 107, 2,6-difluoro-3,5-dimethoxybenzene amine(19mg, O.lOmmol), and HOBT (N-hydroxybenzotriazole, 13.5mg, O.lOmmol) were dissolved in acetonitrile(2mL), and EDCI (57mg, 0.30mmol) was added thereto at room temperature. – After 15 hrs, water and ethyl acetate were added to the reaction mixture. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saline solution, dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting concentrate was purified by silica gel chromatography (DCM:MeOH = 20: 1) to obtain the title compound. NMR (400MHz, DMSO-d6) delta 10.69(s, 1H), 9.39(s, 1H), 8.88(s, 1H), 7.02(s, 1H), 3.84(s, 6H).

The synthetic route of 2,6-Difluoro-3,5-dimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANMI PHARM. CO., LTD.; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; JUNG, Seung Hyun; JUNG, Young Hee; CHOI, Wha Il; SON, Jung Beom; JEON, Eun Ju; YANG, In Ho; SONG, Tae Hun; LEE, Mi Kyoung; KO, Myoung Sil; AHN, Young Gil; KIM, Maeng Sup; HAM, Young Jin; SIM, Tae Bo; CHOI, Hwan Geun; HAH, Jung Mi; PARK, Dong-sik; KIM, Hwan; WO2011/93672; (2011); A2;,
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Synthetic Route of 366-99-4, 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 366-99-4 as follows.

2-pentanone (17.2 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydnde (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stined at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford 3-Fluoro-4-methoxy-N-(pentan-2-yl)aniline(2.1 g, 50percent yield). MS m/z=212 [M+H].

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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Reference of 349-55-3, 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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1 3-(3-Methoxy-5-trifluoromethyl-phenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile To a solution of 3-methoxy-5-trifluoromethyl-anilin(1.50 g, 7.8 mmol) in dry ethyl acetate (10 ml) thiophosgene (0.20 ml, 2.6 mmol) was added dropwise. After stirring for 1.5 h at 75 C. the reaction mixture was cooled on an ice bath and then filtered. The filtrate was concentrated. The residue was dissolved in dry acetone (5 ml) and added to a suspension of methanesulfonylacetonitrile (0.34 g, 2.6 mmol) and dry potassium carbonate (0.72 g, 5.2 mmol) in dry acetone (5 ml). The resulting mixture was stirred at room temperature under nitrogen for 19 h, and then filtered. To the filtrate methyl iodide (0.49 ml, 7.8 mmol) was added. The mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated and the residue was taken up into dichloromethane and water. The organic layer was washed with water (2X), dried (sodium sulfate) and concentrated. The residue was recrystallized from ethyl acetate to give 0.70 g (73%) of the title compound. 1H NMR (200 MHz, CDCl3): delta=2.28 (s, 3H), 3.22 (s, 3H), 3,87 (s, 3H), 7.0 (t, 1H), 7.05 (br s, 1H), 7.14 (br s, 1H), 9.8 (br s, 1H); El SP/MS: 366 (M-2).

The synthetic route of 3-Methoxy-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hansen, John Bondo; Tagmose, Tina Moller; Mogensen, John Patrick; Dorwald, Florencio Zaragoza; Jorgensen, Anker Steen; US2001/25111; (2001); 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. 767-91-9, name is 2′-Methoxyphenyl acetylene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2′-Methoxyphenyl acetylene

Methyl 4-hydroxy-3-iodobenzoate (0.111 g, 0.40 mmol, 2′-methoxyphenyl acetylene (0.052 ml, 0.40 mmol) 1,1,3,3-tetramethylguanidine (0.502 mL, 4.00 mmol) bis(triphenylphosphine)palladium(II)chloride (0.028 g, 0.04 mmol) and copper(I) iodide (1.36 muL, 0.04 mmol) were dissolved in N,N-dimethylformamide (5 mL). The reaction mixture was heated at 50 C. under an atmosphere of argon over night and the solvent was evaporated. Purification by column chromatography, using heptane/ethyl acetate (9:1) as the eluent gave 0.064 g (57% yield) of the title compound.1H NMR (400 MHz, CDCl3), delta ppm 8.34 (d, 1H), 8.07 (dd, 1H), 8.01 (dd, 1H), 7.53 (d, 1H), 7.40 (s, 1H), 7.33-7.39 (m, 1H), 7.06-7.14 (m, 1H), 7.02 (d, 1H), 4.01 (s, 3H), 3.96 (s, 3H).

According to the analysis of related databases, 767-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2009/131468; (2009); A1;,
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Synthetic Route of 2734-70-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2734-70-5 name is 2,6-Dimethoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To an ice-cooled solution of 2,6-dimethoxyaniline (Amfinecom Inc., 2.0 g, 13.1 mmol) in DCM (65 mL) was added N,N-diisopropylethylamine (6.8 mL, 39.2 mmol) followed by cyclobutanecarbonyl chloride (Sigma-Aldrich, 1.56 mL, 13.7 mmol) slowly via syringe. The resulting solution was warmed to RT and stirred for 48 h, then was partitioned between water and DCM (2X). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to provide Example 1.01 (2.92 g, 95percent yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dimethoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 27060-75-9

In a four-necked flask equipped with a thermometer, reflux condenser, stirrer, and nitrogen introduction tube,Add 200g of N-methylpyrrolidone and 15.0g (0.11mol) of acetanilide, stir to dissolve acetanilide in N-methylpyrrolidonein.Add 22g (0.12mol) of 30wt% sodium methoxide and gradually heat to 100 C to distill off methanol to prepare acetanilide sodium salt solution.Add 20.2 g (0.1 mol) 4-bromo-3-methylanisole to the reaction bottle at 20 C for 30 minutes,Control the temperature of the material ? 40 , after the addition is complete, continue to stir the reaction at 40 for 45 minutes.15g of methanol was added, and the temperature was raised to 100 C within 30 minutes, and the low-boiling fraction was distilled off. Then, the reaction was continued at 100 C for 30 minutes.Finally, under vacuum conditions, the temperature is controlled within the range of 110-130 C, and N-methylpyrrolidone is distilled off,A reaction mixture containing the target product 4-methoxy-2-methyldiphenylamine was obtained. Add 200 g of water to the reaction mixture containing 4-methoxy-2-methyldiphenylamine and stir well,Dissolve soluble materials and filter to obtain crude 4-methoxy-2-methyldiphenylamine.The crude 4-methoxy-2-methyldiphenylamine is post-treated by methanol recrystallization, centrifugal separation, drying, etc.Obtained target product 4-methoxy-2-methyldiphenylamine 20.5g, purity 99.3%(Gas chromatography analysis),The reaction yield was 95.3% (based on 4-bromo-3-methylanisole).

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; Shandong Dao Ke Chemical Co., Ltd.; Shandong Morui Technology Co., Ltd.; Li Mingxin; Lu Fengyang; Wang Jiahui; Yang Shuren; Li Mingjing; Yan Xue; (13 pag.)CN104628585; (2016); B;,
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Synthetic Route of 35822-58-3, 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 35822-58-3 as follows.

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

According to the analysis of related databases, 35822-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 50; 4; (2018); p. 416 – 423;,
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Adding a certain compound to certain chemical reactions, such as: 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, belongs to ethers-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 261762-35-0, Quality Control of 5-Bromo-1,2-difluoro-3-methoxybenzene

To a mixture of 6-methoxy-1,2,3,4-tetrahydro-2,7-naphthyridine (500 mg, 3.04 mmol) and 5-bromo-2,3-difluoroanisole (883 mg, 3.96 mmol) in dioxane (8 mL) was added t-BuONa (438 mg, 4.56 mmol), Pd2(dba)3 (40 mg, 0.04 mmol) and Ruphos (30 mg, 0.06 mmol) under N2. After being heated with stirring at 100 C for 12 hrs, the resulting reaction mixture was filtered. Thefiltrate was concentrated in vacuo, diluted with DCM (100 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column to give 2- (3 ,4-difluoro-5-methoxy-phenyl)-6-methoxy-3 ,4-dihydro- 1H- 2,7-naphthyridine (560 mg) as a gray solid.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, belongs to ethers-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 Potassium trifluoro(methoxymethyl)borate

Under an argon atmosphere a mixture of 70 mg of tert-butyl 10-bromo-8-cyclopropyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate (0.172 mmol, 1.00 eq) from step 8.2, 52.2 mg of potassium trifluoro (2-methoxymethyl)borate (0.344 mmol, 2.00 eq), 168 mg of cesium carbonate (0.516 mmol, 3.00 eq), 1.43 mg of Pd(OAc)2 (0.006 mmol, 0.04 eq) and 5.73 mg of X-Phos (0.012 mmol, 0.07 eq) in degassed dioxane (4 mL) and water (0.5 mL) was heated in a microwave at 130 C. for 40 h. Then the mixture was extracted with DCM and the organic phase was washed with water and dried over MgSO4, filtrated and solvent was evaporated to yield the title compound. ESI-MS: m/z (%): 373.30 (100, [M+H]+).

The synthetic route of 910251-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Deutschland GmbH & Co. KG; BACKFISCH, Gisela; BAKKER, Margaretha Henrica Maria; BLAICH, Guenter; BRAJE, Wilfried; DRESCHER, Karla; ERHARD, Thomas; HAUPT, Andreas; KOOLMAN, Hannes; LAKICS, Viktor; LINSENMEIER, Anna; MACK, Helmut; PETER, Raimund; RELO, Ana Lucia; US2015/259343; (2015); A1;,
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