Tag: M.W=100-200

Electric Literature of 6346-09-4, 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. 6346-09-4 name is 4,4-Diethoxybutan-1-amine, 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 a mixture of 4.2 g (20 mmol) of 4-chlorobenzenesulfonyl chloride and 2.5 mL oftrimethylamine in 100 mL of dichloromethane at cooling (5-8 C) was added 3.2 g (20 mmol) of 4,4-diethoxybutan-1-amine. The reaction mixture was stirred at room temperature for 12 h, washed with saturated solution of NaHCO3 (100 mL), the organic layer was separated and evaporated in a vacuum. Yield 5.4 g (93%). 1H NMR spectrum (CDCl3), , ppm: 1.12t (3H, CH3, J 7.0 Hz), 1.38-1.48 m (1H, CH2), 1.69-1.77 m (1H, CH2), 1.81-1.87 m (1H, CH2), 1.91-2.09m (1H, CH2), 3.07-3.15 m (1H, CH2), 3.30-3.39 m(1H, CH2), 3.42-3.50 m (1H, CH2), 3.66-3.72 m (1H, CH2), 5.15-5.19 m (1H, CH), 7.43 d (2H arom, J 8.5 Hz), 7.75 d (2H arom, J 8.5 Hz). 13C NMR spectrum (CDCl3), ppm: 14.98, 14.99, 23.12, 32.76, 47.22, 63.17,90.21, 128.84, 129.25, 137.73, 139.01.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,4-Diethoxybutan-1-amine, and friends who are interested can also refer to it.

Reference:
Article; Smolobochkin; Anikina; Gazizov; Burilov; Pudovik; Russian Journal of Organic Chemistry; vol. 53; 2; (2017); p. 199 – 202; Zh. Org. Khim.; vol. 53; 2; (2017); p. 209 – 212;,
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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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Product Details of 349-55-3

EXAMPLE 33 Preparation of 4-[(3-methoxy-5-trifluoromethyl phenyl)hydrazono]-4H-pyrazole-3,5-diamine In a manner similar to that described in Example 2,4-[(3-methoxy-5-trifluoromethylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 134 mg (0.5 mmol) of 2-[(3-methoxy-5-trifluoromethylphenyl)hydrazono]malononitrile, which was derived from 3-methoxy-5-trifluoromethylaniline (191 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Very little solid had formed after heating the reaction at 75 C. for 1 hr, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to ambient temperature and the solvent was evaporated. The residue was dissolved in ethyl acetate and then precipitated by the addition of hexanes. The resulting solid was isolated by filtration and dried to yield 10 mg (7%) of the title compound as a yellow 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; Zhang, Zaihui; Daynard, Timothy Scott; Sviridov, Serguei V.; Chafeev, Mikhail A.; Wang, Shisen; US2003/60453; (2003); A1;,
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Related Products of 22236-10-8, The chemical industry reduces the impact on the environment during synthesis 22236-10-8, name is 4-(Difluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

Step A: 6-(difluoromethoxy)benzo[d]thiazol-2-amine To 4-(difluoromethoxy)aniline (9.55 g, 60 mmol) in acetic acid (90 niL) was added potassium thiocyanate (KSCN) (12.41 mL, 240 mmol). The mixture was stirred for 20 minutes (KSCN dissolved into solution). To this mixture bromine (3.08 mL, 60.0 mmol) in acetic acid (40 mL) was added dropwise over 20 minutes. The reaction was stirred at room temperature overnight. It was poured into a mixture of 800 ml ice water and 200 ml saturated ammonium hydroxide. The product was extracted with ethyl acetate (5x). The organics were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford 6-(difluoromethoxy)benzo[d]thiazol-2-amine (12.6 g, 52.4 mmol, 87 % yield) as a yellow 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, 4-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; MCDONALD, Ivar, M.; KING, Dalton; OLSON, Richard, E.; WANG, Nenghui; IWUAGWU, Christiana, I.; ZUSI, Christopher, F.; MACOR, John, E.; WO2011/53292; (2011); A1;,
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Related Products of 123652-95-9, 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. 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00330] To a solution of compound 2, 19 and Et3N in DMF at rt. then HATU was added at rt.After stirring for lh at rt, the reaction was diluted with water and extracted with EA, washed byK2C03 and brine, dried over Na2SO4 and concentrated and purified by FCC to afford compound20. ?H NMR (400 MHz, CDC13): 3 8.46 (s, 1H), 8.42 (s, 1H), 7.10-7.06 (m, 2H), 6.94-6.90 (m,1H), 6.47-6.44 (m, 1H), 4.57 (d, J = 6.0 Hz, 2H), 3.87 (s, 3H); mlz (ESI+) (M+H)+ = 313.05.

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, (3-Fluoro-4-methoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; YANG, Wenjin; CHEN, Che-Hong; MOCHLY-ROSEN, Daria; WO2014/160185; (2014); A2;,
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Application of 1535-75-7, 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 1535-75-7 as follows.

A solution of 2.09 g of 2-trifluoromethoxyaniline and 3.15 g of 1-(2-chloroethyl)-4-(2-methoxyphenyl)-piperazine in 20 ml of n-butanol was stirred at 100C for 2 hours. The mixture was then cooled, diluted with water, alkalinised with 2N sodium hydroxide and extracted with chloroform. The organic phase was dried on anhydrous sodium sulphate, evaporated until dry and the crude purified via flash chromatography (ethyl acetate : petroleum ether 3:7) and subsequently crystallised from ethanol giving 0.55 g (12%) of 1-[N-(2-trifluoromethoxyphenyl)-2-aminoethyl]-4-(2-methoxyphenyl)-piperazine. Melting point: 69.5-71C.1H-NMR (CDCl3, delta): 8.02-7.85 (br, 1H, NH), 7.43-7.27 (m, 2H, aniline CHs), 7.03-6.80 (m, 4H, methoxyphenyl ring CHs), 6.72 (dd, 1H, aniline CH), 6.57 (t, 1H, aniline CH), 3.86 (s, 3H, OCH3), 3.43-3.23 (m, 2H, NHCH2CH2), 3.23-3.03 (m, 4H, piperazine protons), 2.85-2.60 (m, 6H, piperazine protons and NHCH2CH2). The title compound was prepared following the procedure described in Example I, second step, except that 1-[N-(2-trifluoromethoxyphenyl)-2-aminoethyl]-4-(2-methoxyphenyl)-piperazine, prepared as described above, was used in place of 1-[N-(2-nitrophenyl)-2-aminoethyl]4-(2-methoxyphenyl)-piperazine and that 4-dimethylaminopyridine was used in place of triethylamine, the mixture being heated for 1.5 h at reflux. The crude material was purified via flash chromatography (ethyl acetate : petroleum ether 4:6). Yield: 44%.1H-NMR (CDCl3, delta): 7.48-7.25 (m, 4H, trifluoromethoxyaniline ring CHs), 7.02-6.81 (m, 4H, methoxyphenyl ring CHs), 4.40-4.20 (m, 1H, C(O)NCH(H)CH2), 3.84 (s, 3H, OCH3), 3.36-3.18 (m, 1H, C(O)NCH(H)CH2), 3.10-2.90 (m, 4H, piperazine protons), 2.75-2.45 (m, 6H, piperazine protons and C(O)NCH2CH2), and 2.03-1.80 (m, 1H, CHC(O)), 1.75-0.80 (m, 10H, cyclohexyl protons).

According to the analysis of related databases, 1535-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RECORDATI S.A.; RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.; EP1000047; (2003); B1;,
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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. 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Formula: C8H9FO2

To a solution of 1-fluoro-3,5-dimethoxybenzene (12.5 g, 80.0 mmol) in dichloromethane (80 ml), cooled to 0 C, was added a 1.0 M solution of BBr3 in dichloromethane (200 ml, 200 mmol), dropwise over a 30 minutes period. The reaction was stirred for 1 hour at 0 C and then slowly warmed to room temperature and stirred for 18 hours. The reaction was cooled to 0 C and quenched by slow addition of MeOH and water. After stirring at room temperature for 1 hour the mixture was filtered and volatiles were removed in vacuo. The solid was washed twice with ethyl acetate; the filtrate was concentrated in vacuo to provide intermediate 8-b as an orange solid.

The synthetic route of 52189-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2014/5217; (2014); A1;,
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Application of 22236-10-8,Some common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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 mixture of 2-[(fert-butyldimethylsilyloxy)methyl]-3-(4,6-dichloro-5- fluoropyrimidin-2-yl)-5-fluoropyrazolo[l,5-a]pyridine (102.0 mg, 0.23 mmol), 4- difluoromethoxy aniline (145.0 mg, 0.92 mmol) and ethanol (1 mL) was heated at 90C overnight. After cooling, the mixture was poured into ice- water to afford a solid. The solid was collected by filtration, followed by washing with water and hexane. The solid was dried under the vacuum to provide 2-[2-[(teri-butyldimethylsilyloxy)methyl]-5-fluoropyrazolo[l,5- a]pyridin-3-yl]-6-chloro-N-(4-difluoromethoxy)phenyl]-J-fluoropyrimidin-4-amine (a mixture of TBS protected and unprotected product).

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; LEE, Chang-Sun; BAIAZITOV, Ramil; CAO, Liangxian; DAVIS, Thomas, W.; DU, Wu; LIU, Ronggang; MOON, Young-choon; PAGET, Steven, D.; REN, Hongyu; SYDORENKO, Nadiya; WILDE, Richard, Gerald; WO2014/81906; (2014); A2;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 171290-52-1

Cul (0.053g, 0.2mmol) was added to the degassed solution of 5-Iodo-N-(2-methyl-6- nitrophenyl)pyrimidin-2-amine (lg, 2.8mmol) and l-ethynyl-3,5-dimethoxybenzene (0.5g, 3.0mmol) in DMF (5mL) followed by the addition of tetrakis (0.32g, 0.2mmol) in a sealed tube. Stirred the reaction mass for 10 min and added DIPEA (0.75mL, 4.2mmol) and heated the resultant reaction mass to 80 C for 2h. Reaction mass was filtered through celite and washed the celite bed with ethyl acetate. The organic layer washed with water followed by brine, dried over Na2S04, filtered and concentrated. The residue was purified by 60-120 silica gel column chromatography to afford desired title compound (0.7g, 66%). LCMS: m/z = 391.1 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 171290-52-1.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
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Related Products of 150-78-7, These common heterocyclic compound, 150-78-7, name is 1,4-Dimethoxybenzene, 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 stirred solution of starting compound (0.5-1.2 mmol) in DMF-H2O (95:5, v/v, 8-12 mL) mixture was added NBS (4.0-4.2 mmol) at room temperature. The contents were stirred at room temperature about 10 min and then heated for appropriate duration mentioned in Table 2. Progress of the reaction in every case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with aqueous NaHCO3 (20%, 20-30 mL) solution. The insoluble precipitate was isolated by filtration and dried in vacuo. It was further purified by either recrystallization with ethyl acetate/n-hexane mixture or short pad silica gel column chromatography led to pure product.

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Natarajan, Palani; Vagicherla, Vinuta Devi; Vijayan, Muthana Thevar; Tetrahedron Letters; vol. 55; 24; (2014); p. 3511 – 3515;,
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Application of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 solution of 1,4-dimethyl-3-formylcarbazole (500 mg, 2.2 mmol) in benzene (15 mL) and 2,2-diethoxyethylamine (330 mg, 2.5mmol) was placed in a flask. The mixture was refluxed for 2 h. After the reaction, the solvent was evaporated under the reduced pressure. MeOH (15 mL) was added to the residue. NaBH4 (800 mg, 22mmol) was then added slowly, and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated under the reduced pressure. The residue was extracted with CHCl3 and dried over Na2SO4, andconcentrated under reduced pressure. A solution of the residue in a mixture of MeCN (10 mL) andpyridine (1 mL) was placed in a flask. After the solution was stirred at rt for 0.5 h, 2-nitrobenzenesulfonylchloride (1.0 g, 4.5 mmol) was added, and the reaction mixture was stirred at rt for 24 h. After thereaction, the solvent was evaporated under reduced pressure. The crude product was recrystallized from MeOH, affording N-(2,2-diethoxyethyl)-N-((1,4-dimethyl-9H-carbazol-3-yl)methyl)-2-nitrobenzenesulfonamide (85%, 1.0 g); yellow solid; mp 175.0-176.0 C; 1H NMR (500 MHz, CDCl3) delta 1.46 (6H, t, J= 7 Hz), 2.41 (3H, s), 2.73 (3H, s), 3.41-3.46 (4H, m), 3.61-3.64 (2H, m), 4.56 (1H, t, J = 5.5 Hz), 4.88(2H, s), 7.07 (1H, s), 7.21-7.26 (1H, m), 7.36-7.42 (2H, m), 7.47 (1H, d, J = 8 Hz), 7.52 (1H, d, J = 8 Hz),7.60 (1H, d, J = 8 Hz), 7.77 (1H, d, J = 8 Hz), 8.03 (1H, brs), 8.15 (1H, d, J = 8 Hz); 13C NMR (CDCl3,125 MHz) delta 15.3, 15.9, 16.5, 49.6, 50.6, 63.4, 102.2, 110.6, 116.8, 119.5, 121.9, 122.8, 123.7, 123.8,124.3, 125.1, 128.7, 130.4, 130.8, 131.1, 132.8, 134.4, 138.4, 139.6, 147.8; MS (FAB+) m/z 525 [M+];HRMS (FAB+): calcd for C27H31N3O6S (M+) 525.1933, found 525.1921.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Diethoxyethanamine, its application will become more common.

Reference:
Article; Sato, Naoya; Kawai, Yu; Akaba, Yosuke; Honma, Shoji; Sakai, Norio; Konakahara, Takeo; Heterocycles; vol. 92; 4; (2016); p. 664 – 679;,
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