Month: July 2021

Application of 78531-29-0, A common heterocyclic compound, 78531-29-0, name is 1,3-Dimethoxypropan-2-amine, molecular formula is C5H13NO2, 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.

4-Bromo-1-fluoro-2-nitrobenzene (commcerciaHy available from, for example, Aldrich) (50 g, 227 mmol) and l,3-dimethoxypropan-2-amine (commcerciaHy available from, for example, Aldrich) (32.5 g, 273 mmol) were dissolved in acetonitrile (300 mL) and potassium carbonate (47.1 g, 341 mmol) was added, then the mixture was stirred at 80 C for 6 h, then the mixture was allowed to cool and stood over the weekend at room temperature. The mixture was diluted with water (500 mL) and extracted with EtOAc (2 x 500 mL). The organic layer was washed with water (300 mL) and brine (300 mL), dried and evaporated in vacuo to give the title compound (70 g, 220 mmol, 97% yield) as an orange solid.

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; Glaxosmithkline Intellectual Property Co.,Ltd; BROWN, JOHN ALEXANDER; G HUMPHREYS, PHILIP; JONES, KATHERINE LOUISE; WELLAWAY, CHRISTOPHER ROLAND; (48 pag.)TW2017/4230; (2017); A;,
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These common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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. COA of Formula: C10H10O2

General procedure: Glass reactor (3 mL) equipped with a condenser and a stirringbar was charged under argon with arylacetylene (9.11 104 mol),EtOH (99.8%) (2 mL) and catalyst 8 (0.25-2.0 mol% in relation toacetylene). The reaction mixture was stirred at 22 C for 24 h. Thenthe solventwas evaporated under reduced pressure and the residuewas purified by column chromatography (silica gel, hexane/CH2Cl2 = 4/1). Evaporation of the solvent gave an analytically pureproduct.

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

Reference:
Article; Ostrowska, Sylwia; Szymaszek, Natalia; Pietraszuk, Cezary; Journal of Organometallic Chemistry; vol. 856; (2018); p. 63 – 69;,
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Related Products of 157869-15-3, The chemical industry reduces the impact on the environment during synthesis 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, I believe this compound will play a more active role in future production and life.

General procedure: 2-(phenylethynyl)aniline (302.8 mg, 1.57 mmol, 1.0 equiv) was dissolved in DCM (5.0 mL) and cooled to 0 C. The solution was then added with Et3N (0.24 mL, 174.1 mg, 1.72 mmol, 1.1equiv), followed by acetyl chloride (0.18 mL, 198.0 mg, 2.52 mmol, 1.6 equiv). The resulting reaction mixture was allowed to stir at 0 C while slowly warming to room temperature over 5 h,at which point the reaction was complete as indicated by TLC. The reaction mixture was byaddition of water. The separated aqueous phase was extracted with DCM (3x times). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4, filtered and concentrated to a crude solid. The crude solid product was purified by SiO2 column chromatography eluting with 20% EtOAc-hexane to give 354.4 mg (96%) of compound 1a as awhite solid.

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, 2-((4-Methoxyphenyl)ethynyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chaisan, Nattawadee; Kaewsri, Wilailak; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Ruchirawat, Somsak; Tetrahedron Letters; (2018); p. 675 – 680;,
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Synthetic Route of 41789-95-1, The chemical industry reduces the impact on the environment during synthesis 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

General procedure: A solution of bromo heteroaryl carboxylic acid (2mmol), thionyl chloride (4mmol) and DMF (5 drops) in toluene (10mL) was refluxed at 110C for 4h. The reaction mixture was cooled to room temperature and the solvent and the excess of thionyl chloride removed under reduced pressure. To the residue was added at 0C the corresponding N-methyl amine (2mmol) and Et3N (2mmol) in CH2Cl2 (10mL) under N2 atmosphere. After 30min at 0C, the ice bath was removed and the solution was warmed up and stirred at room temperature overnight. The reaction mixture was extracted twice with CH2Cl2 (2×15mL) and the organic layer dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexanes and EtOAc as eluant or by trituration in a mixture of diethyl ether/petroleum ether to afford the desired compound.

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, 1-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Perspicace, Enrico; Cozzoli, Liliana; Gargano, Emanuele M.; Hanke, Nina; Carotti, Angelo; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 317 – 337;,
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Synthetic Route of 767-91-9, These common heterocyclic compound, 767-91-9, name is 2′-Methoxyphenyl acetylene, 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.

Table 5. Copper catalyzed carboxylation of terminal alkynes with CCv Reaction conditions: for LI, CuCl (2.0 mol %), TMEDA, 1.5 mol %; for L12, P(NHC)(NHC-Cu), 5 mol%; alkynes (2.0 mmol), base (2.4 mmol), C02 (1 atm), DMF (4 mL), r.t.. M monocarboxylic acid was obtained. General Procedure for Carboxylation of the Terminal Alkynes (lb as Example); CuCl (4.0 mg, 0.04 mmol, 2.0 mol %), TMEDA (3.5 mg, 0.03 mmol, 1.5 mol %), and K2C03 or Cs2C03 (2.4 mmol) were added to the DMF (4 mL) in the reaction tube (10 mL). C02 and 2 mmol of terminal alkynes (la, 204 mg) were introduced into the reaction mixture under stirring. The reaction mixture was stirred at room temperature (about 24 C) for 16 hours. After completion of the reaction, the reaction mixture was transferred to the potassium carbonate solution (2 N, 5 mL) and the mixture was stirred for 30 mins. The mixture was extracted with dichloromethane (3 >< 5 mL) and the aqueous layer was acidified with concentrated HC1 to PH = 1 , then extracted with diethyl ether (3 chi 5 mL) again. The combined organic layers were dried with anhydrous Na2S04, filtered and the solution was concentrated in vacuum affording pure product. Element analysis calcd (%) for lb [C9H602 (146.0)]: C 73.97, H 4.14; found: C 73.82, H 4.07. Data for 1H and 13C NMR of acids were all conducted in d - DMSO or CDC13 and consistent with the data in reported literatures. The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; ZHANG, Yugen; YU, Dingyi; WO2011/75087; (2011); A1;,
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Application of 22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The nitro ether (149 mmol) was dissolved in ethanol (37.5 mL), diluted with water (25 mL), and was treated with ammonium chloride (84.7 mmol) and iron powder (105 mmol). The reaction mixture was heated at reflux for 30 minutes and the suspension was filtered through Celite. The filter cake was washed with ethanol three times and the combined filtrates were concentrated. The residue was dissolved in water and the pH adjusted to 9-10 with 5 M sodium hydroxide. The aqueous layer was extracted with ethyl acetate (3xlOOmL) and the combined organic layers were dried (magnesium sulfate) and concentrated to a yellow oil. The oil was dissolved in acetic anhydride (23.5 mmol) and the reaction mixture was maintained at rt for 16 h. The reaction mixture was diluted with water (50 mL) and was neutralized with solid sodium bicarbonate. The precipitated solids were isolated by filtration, washed with water, and dried to provide the acetamide in 62% yield as a light yellow solid.

The synthetic route of 4-(Difluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/63767; (2005); A2;,
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Some common heterocyclic compound, 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene, molecular formula is C9H10BrFO, 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: 202865-80-3

Intermediate 12 2-(3-fluoro-4-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane :Potassium acetate (10.52 g, 107.2 mmol) and bis(pinacolato)diboron (15 g, 58.96 mmol) were added to a solution of intermediate 11 (10.52 g, 107.2 mmol) in dioxane (125 ml), and the solution was degassed for 30 min. [1,1′-Bis(diphenylphosphino)ferrocene]dichloro palladium(II).CH2Cl2 (4.4 g, 5.36 mmol) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate :petroleum ether to afford the title compound as a yellow oil (13.9 g, 99%) which was used without purification in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 202865-80-3, its application will become more common.

Reference:
Patent; Rhizen Pharmaceuticals SA; US2012/289496; (2012); A1;,
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Synthetic Route of 60792-79-2, 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. 60792-79-2 name is 2,2′-Oxybis(ethylamine) dihydrochloride, 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.

Vancomycin (16.0 g, 11.2 mmol, 1.0 eq) was dissolved in [H20] (100 mL) and treated with a solution of 5-amino-3-oxo-pentylamine dihydrochloride salt (10.0 g, [56] mmol, 5 eq) in H2O [(30] mL) and the reaction mixture was stirred at ambient temperature. Triethylamine (22 mL, 160 mmol) was then added, followed by an aqueous solution of formaldehyde (37%, 1. 05 mL, 11.2 mmol) and the reaction mixture was stirred at ambient temperature for one hour. The reaction mixture was diluted with water/acetonitrile (1: 1; 200 mL) and lyophilized. The resulting mixture was dissolved in H2O (50 mL) and purified using large scale HPLC (0-12% gradient over 40 minutes) to provide, after lyophilization, the title compound as a white amorphous powder (7.2 g). HPLC (2-30% gradient): 2.4 min. MS m/z : 1566.9 [M + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2′-Oxybis(ethylamine) dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; THERAVANCE, INC.; WO2003/99858; (2003); A1;,
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Synthetic Route of 19500-02-8, 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 19500-02-8 as follows.

A. N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. By the method in Example 1, Part A, 25.8 g (188 mmol) of 3-methoxy-2-methylaniline was treated with 41 g (188 mmol) of di-tert-butyl dicarbonate to give by chromatography on silica (eluted with 25percent EtOAc/hexane) 16.4 g (80percent yield) of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. Analysis: Calc’d for C13 H19 NO3: C, 65.80; H, 8.07; N, 5.90. Found: C, 64.31; H, 7.76; N, 6.58.

According to the analysis of related databases, 19500-02-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US5684034; (1997); A;,
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Related Products of 109-85-3, 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. 109-85-3, name is 2-Methoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-amino-4-fluoronicotinonitrile 7 (4.11 g, 30 mmol), 2-methoxyethanamine (4.5 g, 60 mmol), and DIPEA (1.16 g, 90 mmol) in DMF (120 mL) was stirred at 60C until the reaction was completed by TLC. After quenched with water, the reaction solution was extracted with CH2Cl2 (3 ×100 mL), washed with sequentially with satd NaHCO3 (aq) and brine and then dried over anhydrous Na2SO4. Filtration, evaporation, and chromatography on silica gel afforded the product 8 (3.84 g, 67%). MS m/z (ESI): 193.1 [M+H]+.

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

Reference:
Article; Sun, Chang’an; Fang, Lei; Zhang, Xiaobing; Gao, Peng; Gou, Shaohua; Bioorganic and Medicinal Chemistry; vol. 27; 10; (2019); p. 1932 – 1941;,
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