Author: Jessica.F

Electric Literature of 5414-19-7, The chemical industry reduces the impact on the environment during synthesis 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, I believe this compound will play a more active role in future production and life.

TP5 – To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5- dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ of bis (2-bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). XH NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J= 8.8, 2H), 6.92 (d, J= 8.8, 2H), 3.99 – 3.76 (m, 4H), 3.44 – 3.31 (m, 1H), 3.29 – 3.22 (m, 4H), 2.70 (dd, J= 6.7, 16.8, 1H), 2.46 (d, J= 16.7, 1H), 1.24 (d, J= 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 16.36. MS: 274 (M + 1). Anal. Calcd. for C15H19N3O2: C, 65.91; H, 7.01 ; N, 15.37; Found. 65.81, H, 6.66, N, 15.26.

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-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BROAD INSTITUTE, INC.; DANA FARBER CANCER INSTITUTE, INC.; LEWIS A., Timothy; MUNOZ, Benito; DE WAAL, Lucian; GREULICH, Heidi; MEYERSON, Matthew; GECHIJIAN, Lara Nicole; WO2014/164704; (2014); A2;,
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Electric Literature of 75148-49-1, 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. 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, This compound has unique chemical properties. The synthetic route is 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.

The chemical industry reduces the impact on the environment during synthesis 3-Bromobenzaldehyde Diethyl Acetal. I believe this compound will play a more active role in future production and life.

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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123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, 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. SDS of cas: 123652-95-9

General procedure: Spirothiazamenthane 3 (1.0 eq) was dissolved in toluene (0.1 M concentration) in a microwave vial and the solution was treated with amine (10 eq) and PTSA (20 mol %). This mixture was heated at 150 C using microwaves for 4 h. After cooling, the solvents were removed by evaporation and the resulting residue was taken up in 1:1 Et2O/2M NaOH. The layers were separated and the aqueous layer was extracted 2 ¡Á with Et2O. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The resulting crude products were purified as described below. Variations in reaction conditions are also noted below.

The synthetic route of 123652-95-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arns, Steve; Balgi, Aruna D.; Shimizu, Yoko; Pfeifer, Tom A.; Kumar, Nag; Shidmoossavee, Fahimeh S.; Sun, Sharon; Tai, Sheldon S.-H.; Agafitei, Olga; Jaquith, James B.; Bourque, Elyse; Niikura, Masahiro; Roberge, Michel; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 64 – 73;,
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Application of 886762-08-9, 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N-(5-bromo-2-(trifiuoromethoxy)phenyl)acrylamide (2): To a solution of 5-bromo- 2-(trifiuoromethoxy)aniline (1.2 g, 4.7 mmol) in dichloromethane (5.0 niL), diisopropylethylamine (727 mg, 5.64 mmol) and acryloyl chloride (382 mg, 4.22 mmol) were added at -78 C. The reaction mixture was allowed to stir at 0 C for 2 h. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2 (1.4 g, 93%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) : delta 5.79-5.80 (dd, J = 1.82 Hz, 10.2 Hz, 1H), 6.26-6.27 (dd, J = 1.8, 17.0 Hz, 1H), 6.61-6.63 (dd, J = 17.0 Hz, 1H), 7.38-7.40 (m, 2H), 8.28-8.29 (d, J = 2.3 Hz, 1H), 10.07 (brs, 1H). MS m/z (M+H): 310.45

The synthetic route of 5-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
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Related Products of 19500-02-8, These common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-methylaniline, 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.

Part A. Preparation of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. A solution of 44.4 g (344 mmol) of 3-methoxy-2-methylaniline and 75 g (344 mmol) of di-tert-butyl dicarbonate in 400 mL of THF was heated to maintain reflux for 4 hours. After concentrating at reduced pressure, the residue was taken up in ethyl acetate, washed with 1N citric acid, water and dried (MgSO4). After removing the solvent at reduced pressure, the residue was crystallized from hexane to give 64.5 g (84percent yield) of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline, mp, 56-57¡ã C. Analysis for C13H19NO3: Calculated: C, 65.80; H, 8.07; N, 5.90 Found: C, 63.32; H, 7.83; N, 5.56.

Statistics shows that 3-Methoxy-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 19500-02-8.

Reference:
Patent; Loh, Andrew; Macias, William Louis; Skerjanec, Simona; US2004/110825; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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 1836-62-0, Application In Synthesis of 2-(2-Methoxyphenoxy)ethylamine

EXAMPLE 1a [(cis)-4-(5-Fluoro-1H-indol-3-yl)-cyclohexyl]-[2-(2-methoxy -phenoxy)-ethyl]-amine A solution of 4-(5-fluoro-1H-indol-3-yl)-cyclohexanone (0.38 g,1.6 mmol), [2-(2-methoxy-phenoxy)-ethyl]-amine (0.27 g, 1.6 mmol), sodium triacetoxyborohydride (0.5 g, 2.2 mmol) and acetic acid (0.06 ml, 1.8 mmol) in 1,2-dichloroethane (8 ml) was allowed to stir at room temperature for 4 hours. The reaction was quenched with 1N sodium hydroxide (10 ml), extracted with methylene chloride (3 x 60 ml) and washed with brine (3 x 60 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. Chromatography (10% methanol-ethyl acetate) afforded 0.43 g(71%) of product as a white solid. The HCl salt was prepared in ethyl acetate: mp 186-188C.

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

Reference:
Patent; Wyeth; EP1068184; (2002); 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. 19500-02-8, name is 3-Methoxy-2-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 19500-02-8

[00194] lambda/-fe^Butyloxycarbonyl-2-methyl-3-methoxyaniline (3); [04-035-12]. A stirred solution of amine 2 (42.58 g, 0.31 mol) and di-te/t-butyl dicarbonate (65.48 g, 0.30 mol) in THF (3(T.sect.-m(L) was ‘heated to maintain reflux for 4 h. After cooling to RT, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc (500 mL). The resultant solution was washed with 0.5 M citric acid (2×100 mL), water (100 mL), saturated aqueous NaHCO3 (200 mL), brine (200 mL) and dried over MgSO4. After filtration and removal of the solvent from the filtrate, the residue (red oil, 73.6 g) was dissolved in hexanes (500 mL) and filtered through a pad of Silica Gel (for TLC). The filtrate was evaporated under reduced pressure to provide lambda/-Boc aniline 3 as a yellow solid. Yield: 68.1 g (96percent).

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; ILYPSA, INC.; WO2007/56275; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 78531-29-0, name is 1,3-Dimethoxypropan-2-amine, 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 78531-29-0, Recommanded Product: 1,3-Dimethoxypropan-2-amine

To a dry (0876) 200 round-bottomed flask was added di(2-pyridyl) thionocarbonate (5.34 g, 23.00 mmol) in DCM (73.0 ml). 2-Amino-l,3-dimethoxypropane (commericially available from Combi-Blocks Inc., 2.61 g, 21.90 mmol) in DCM (15 mL) was then added dropwise via an addition funnel over 5 min at RT with stirring. The reaction mixture was stirred at RT for 3.5 h. The reaction mixture was then concentrated in vacuo. The product was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% EtOAc in heptane, to provide the title compound Example 124.1 (3.28 g, 20.34 mmol, 93 % yield) as colorless oil. NMR (400MHz, CDC13) delta 3.95 (quin, J=5.49 Hz, 1 H) 3.50 – 3.60 (m, 4 H) 3.41 (s, 6 H). LCMS (pos.) m/z: 162.2 (M+H)+.

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-Dimethoxypropan-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
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Synthetic Route of 109-85-3, The chemical industry reduces the impact on the environment during synthesis 109-85-3, name is 2-Methoxyethylamine, I believe this compound will play a more active role in future production and life.

To a colorless solution of methyl 3-fluoro-4-nitrobenzoate (50 g, 250 mmol) in THF (400 ml_) was added triethylamine (40.7 g, 402 mmol, 55.8 ml_) followed by addition of 2- methoxyethanamine (30.2 g, 402 mmol) in THF (100 ml_), drop-wise, at room temperature. The resultant yellow solution was stirred at 55 C for 18 hours. The solution was cooled to room temperature and concentrated under reduced pressure to remove THF. The resultant yellow solid was dissolved in EtOAc (800 ml_) and washed with saturated aqueous ammonium chloride solution (250 ml_). The aqueous phase was separated and extracted with EtOAc (200 ml_). The combined organic layers were washed with saturated aqueous sodium chloride solution (3 x 250 ml_), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield C49 (60.2 g, 94%) as a yellow solid. 1H NMR (CDCb) d 8.23 (d, 1 H), 8.17 (br s, 1 H), 7.58 (d, 1 H), 7.25 (dd, 1 H), 3.95 (s, 3H), 3.69 – 3.73 (m, 2H), 3.56 (m, 2H), 3.45 (s, 3H); LCMS m/z 255.4 [M+H]+.

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-Methoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; ASPNES, Gary Erik; BAGLEY, Scott W.; CONN, Edward L.; CURTO, John M.; EDMONDS, David James; FLANAGAN, Mark E.; FUTATSUGI, Kentaro; GRIFFITH, David A.; HUARD, Kim; LIMBERAKIS, Chris; MATHIOWETZ, Alan M.; PIOTROWSKI, David W.; RUGGERI, Roger B.; (149 pag.)WO2019/239371; (2019); A1;,
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Application of 910251-11-5, 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 910251-11-5 as follows.

A 100-mL round-bottom flask charged with compound 1-2 (100 mg, 0.26 mmol, 1.00 equiv), p and potassium methoxylmethyltrifluoroborate (77.9 mg, 0.51 mmol, 2.00 equiv) in dioxane (30 mL) and water (3 mL). Then Pd(pddf)Cl2 (50 mg) and Cs2C03 (250 mg, 0.76 mmol, 3.00 equiv) were added and the resulting mixture was degassed three times with nitrogen and stirred overnight at 85C. The resulting mixture was diluted with 30 mL of water and was extracted with 3 x 50 mL of ethyl acetate. Organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by preparative HPLC to furnish 8.2 mg (9%) of 6-(methoxymethyl)-N-((lr,4r)-4- morpholinocyclohexyl)quina-zolin-4-amine, 1-32 as a white solid. LCMS (ES, m/z): 357.2 [M+H]+; 1H NMR (300 MHz, CD3OD) delta 8.43 (s, 1H), 8.19 (s, 1H), 7.77 (dd, 1H), 7.69 (d, 1H), 4.62 (s, 2H), 4.26-4.19 (m, 1H), 3.74 (t, 4H), 3.45 (s, 3H), 2.66 (t, 4H), 2.39 (d, 1H), 2.39 (d, 2H), 2.34 (d, 2H), 1.62-1.42 (m, 4H).

According to the analysis of related databases, 910251-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; SHELLEY, Mee; MASSE, Craig E.; HARRIMAN, Geraldine C.; WO2015/164374; (2015); A1;,
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