Ethers-buliding-blocks

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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., COA of Formula: C9H13NO

B) (4S)-Lambda/-((1 S)-1-r4-(methyloxy)phenyllethyll-3.4-dihvdro-2H-pyranor3.2-lpyridin-4- amine: To a solution of crude 2,3-dihydro-4/-/-pyrano[3,2-]pyridin-4-one (2.43 g) in 1 ,2- dichloroethane was added {(1S)-1-[4-(methyloxy)phenyl]ethyl}amine EPO (2.49 g, 16.5 mmol) and acetic acid (1.4 ml_, 24.5 mmol). The reaction mixture was stirred for 1 hour, then sodium triacetoxyborohydride (5.18 g, 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours, then diluted with dichloromethane and quenched with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 10% aqueous NH4OH in acetonitrile) provided (4S)- Lambda/-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-3,4-dihydro-2/-/-pyrano[3,2-/j]pyridin-4-amine (1.90 g, 38% two step yield) as a brown oil. 1H NMR (400 MHz, CDCI3) delta 8.15 (dd, J = 3.0, 3.0 Hz, 1 H), 7.35 (d, J = 8.6 Hz, 2 H), 7.07 (d, J = 2.8 Hz, 2 H), 6.86 (d, J = 8.7 Hz, 2 H), 4.19 (ddd, J = 11.0, 7.7, 3.3 Hz, 1 H), 4.07 (q, J = 6.5 Hz, 1 H), 4.00 (ddd, J = 11.1 , 7.3, 3.5 Hz, 1 H), 3.91 (t, J = 5.7 Hz, 1 H), 3.80 (s, 3 H), 2.32 (br, 1 H), 1.70 (m, 2 H), 1.44 (d, J = 6.6 Hz, 3 H).

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
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150-78-7, name is 1,4-Dimethoxybenzene, 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. Application In Synthesis of 1,4-Dimethoxybenzene

Paraformaldehyde (Aldrich, 4.27 g, 144.75 mmol) and HBr/AcOH (Fluka, 33%, 30 mL) were added slowly to a stuffed solution of 1,4-dimethoxybenzene (Aldrich, 10.00 g, 72.37 mmol) in glacial acetic acid (Fisher, 50 mL). The mixture was stirred at 50C for one hour, allowed to cool to room temperature, and then hydrolyzed in water (200 mL). The white solid was collected by filtration, suspended in CHC13 (50 mL), and refluxed for 10 mm. After cooling to room temperature, the white solid was again collected by filtration and washed with water (15.75 g, 67%). NMR spectra were obtained experimentally to confirm the chemical structure of the resulting compound and its purity. NMR results were as follows: ?H NMR (300 MHz, CDC13) 6:6.88 (s, 2H), 4.54 (s, 4H), 3.87 (s, 6H) ppm.

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

Reference:
Patent; ROBERT BOSCH GMBH; MARUNIAK, Autumn; AHMAD, Habib; RAGHUNATHAN, Ashwin; JOHNSON, Christopher; KAVUSI, Sam; FOMINA, Nadezda; LANG, Christoph; (170 pag.)WO2017/5587; (2017); A1;,
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Related Products of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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.

The product of Example 33D (62 mg, 0.2 mmol) was treated with triethyl orthobenzoate (Aldrich, 0.5 mL) in DMF (1 mL) at 100° C. for 10 h. It was then concentrated. The title product was purified by preparative HPLC (Xterra.(TM)., column, Xterra RP-18, 5 mum, 30.x.100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10), (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (40.0 mg, 50percent). 1H NMR (500 MHz, CD3OD) delta 1.52-1.64 (m, 1 H), 1.68-1.80 (m, 1 H), 1.80-1.92 (m, 1 H), 2.06-2.18 (m, 1 H), 2.25-2.31 (m, 1 H), 2.75-3.10 (m, 5 H), 3.39-3.49 (m, 1 H), 5.14-5.27 (m, 1 H), 7.55-7.66 (m, 3 H), 7.69 (dd, J=8.5, 1.8 Hz, 1 H), 7.81 (d, J=8.2 Hz, 1 H), 8.00 (d, J=1.5 Hz, 1 H), 8.27 (dd, J=8.1, 1.7 Hz, 2 H), 8.89 (s, 2 H) ppm; MS (DCl/NH3): 399 (M+H)+.

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

Reference:
Patent; Abbott Laboratories; US2005/137204; (2005); A1;,
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Reference of 349-65-5,Some common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
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78531-29-0, name is 1,3-Dimethoxypropan-2-amine, 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. Quality Control of 1,3-Dimethoxypropan-2-amine

General procedure: Example 6B (0.018 g, 0.05 mmol) was dissolved in acetonitrile (0.5 ml), and treated with potassium carbonate (0.021 g, 0.15 mmol) and 1 -(2-chloroethyl)pyrrolidine (0.017 g, 0.1 mmol). The reaction mixture was heated via microwave at 180 C for 30 minutes, concentrated in vacuo, and submitted to reverse-phase HPLC (as described in Example 6C) to provide the title compound.

The synthetic route of 78531-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; SWEIS, Ramzi F.; CURTIN, Michael L.; PLIUSHCHEV, Marina A.; HANSEN, Todd M.; LONGENECKER, Kenton; WO2013/170118; (2013); 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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Related Products 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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Some common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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. name: 1,3-Dibromo-2,2-dimethoxypropane

To a suspension of NaH (4.1 g, 100 mmol) (60% in mineral oil) in DMF (100 mL) was added 2-(4-bromophenyl)acetonitrile (10 g, 51 mmol) followed by l,3-dibromo-2,2-dimethoxypropane (11 g, 42 mmol). The reaction mixture was heated to 60 C for 12 h. After 12 h the reaction mixture was diluted with water (1000 mL) and washed with EtOAc (400 mLx2). The combined organics were washed with brine (100 mL), dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica (petroleum ether : EtOAc = 50: 1 to 20: 1) to afford 1-(4-bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile. MS (ESI) Calc’d [M+H]+, 296; found, 296.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22094-18-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; SCIAMMETTA, Nunzio; WHITE, Catherine, M.; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (109 pag.)WO2019/74747; (2019); A1;,
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Reference of 592-55-2, 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. 592-55-2, name is 1-Bromo-2-ethoxyethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(A) A mixture of 4-bromo-3-methylphenol (10 g, 53.47 mmol), 1-bromo-2-ethoxyethane (10.62 g, 69.40 mmol) and K2CO3 (11.13 g, 79.95 mmol) in DMF (100 mL) was stirred overnight at 75 C. After cooling to rt, brine (250 mL) was added and the mixture was extracted with EtOAc (4*100 mL). The combined organic extracts were washed with brine (4*100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (5% EtOAc/petroleum ether afforded 1-bromo-4-(2-ethoxyethoxy)-2-methylbenzene (12.25 g, 88%) as light yellow oil which was used directly.

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

Reference:
Patent; Janssen Pharmaceutica NV; Liang, Yin; Demarest, Keith T.; (109 pag.)US2017/290800; (2017); 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., Computed Properties of C9H8O

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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