Month: January 2021

Related Products of 89521-55-1, A common heterocyclic compound, 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, molecular formula is C13H14N2O, 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.

To a solution of Compound (6) (1.0 g), 3-(benzyloxy)-1,2-benzenediamine (817 mg) and 1-hydroxybenzotriazole (567 mg) in N,N-dimethylformamide (19 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (804 mg). After stirring for 6 hrs, saturated aqueous NaHCO3 (20 mL) and water (80 mL) were added to the reaction mixture. The resulting precipitate was collected by filtration and washed with water. To a mixture of this product in acetic acid (7 mL) was added a solution of hydrogen chloride in acetic acid (13 mL). After stirring at 100 C. for 1 hour, the resulting mixture was cooled to 4 C. and diluted with ethyl acetate (40 mL). The resulting precipitate was collected by filtration and washed with ethyl acetate. To a solution of this product, O-tetrahydro-2H-pyran-2-ylhydroxylamine (1.5 eq.) and 1-hydroxybenzotriazole (1.5 eq.) in N,N-dimethylformamide (11 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.5 eq.) at 4 C. The mixture was warmed to ambient temperature and stirred for 8 hrs. The reaction mixture was added saturated NaHCO3 (11 mL) and water (44 mL). A resulting precipitate was filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was treated with trifluoroacetic acid to give Compound E120 (52 mg). 1H-NMR (300 MHz, DMSO-d6, delta): 4.43 (2H, s), 6.46 (1H, d, J=16 Hz) 6.86 (1H, d, J=8 Hz), 7.12(1H, d, J=8 Hz), 7.23-7.30 (1H, m), 7.39-7.62 (5H, m);

The synthetic route of 89521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; US2004/229889; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Intermediate 8 (1.70 g, 8.015 mmol) was dissolved in N, N-dimethylformamide (20 mL)Placed in a sealed tube,2,2′-dibromodiethyl ether (1.4 mL, 8.816 mmol) and N, N-diisopropylethylamine (2.7 mL, 16.03 mmol) were added.The reaction was heated to 100 C,Stir for 16 hours.Cooled to room temperature,Ethyl acetate was added,Washed,The organic phase is dried,Filtered and concentrated under reduced pressure,The crude product was purified by column chromatography,To give intermediate 9 (2.23 g) in 42% yield.

Statistics shows that 1-Bromo-2-(2-bromoethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 5414-19-7.

Reference:
Patent; Shanghai Hansoh BioMedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Zhao, Zhiming; Wu, Chenchen; Yu, Hongping; Xu, Yaochang; Pan, Zhongzong; Bao, Rudi; (26 pag.)CN106349180; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 41406-00-2, 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. 41406-00-2, name is 3-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 86; N-[(2-Cyclohexyl-4-hydroxy-1-{3-[(1-methylethyl)oxy]phenyl}-6-oxo-1,6-dihydro-5-pyrimidinyl)carbonyl]glycine; 86a) 2-Cyclohexyl-6-hydroxy-3-{3-[(1-methylethyl)oxy]phenyl}-4(3H)-pyrimidinone; 1M Dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred solution of 3-isopropoxyaniline (0.378 g, 2.50 mmol) and cyclohexanecarbonitrile (0.328 g, 3.00 mmol) in toluene (2 mL) and the mixture stirred for 15 min at room temperature under nitrogen, then microwaved at 150 C. for 30 min. After cooling, the solvent was removed under reduced pressure and diethyl malonate (1.52 mL, 10.0 mmol) added, followed by 2-methoxyethanol (5 mL) and methanolic sodium methoxide (2.30 mL, 10.0 mmol) and the mixture refluxed under nitrogen for 18 h, then cooled and poured into water (70 mL). The mixture was washed with ether, then acidified to pH 1 with 6M aqueous hydrochloric acid and extracted again with ethyl acetate. The extracts were washed with water, brine, dried (MgSO4) and evaporated under reduced pressure. The residue was chromatographed (silica gel, 1-9% methanol/dichloromethane) and the product triturated with ether. The solid was collected, washed with ether and dried to give the title compound (0.117 g, 14%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.78-0.94 (m, 2 H) 1.04-1.17 (m, 1 H) 1.24 (d, J=6.06 Hz, 3 H) 1.28 (d, J=6.06 Hz, 3 H) 1.41-1.59 (m, 3 H) 1.59-1.84 (m, 4 H) 2.16 (tt, J=11.53, 3.16 Hz, 1 H) 4.66 (sept, J=5.98 Hz, 1 H) 5.30 (s, 1 H) 6.78-6.86 (m, 1 H) 6.91-6.96 (m, 1 H) 6.98-7.05 (m, 1 H) 7.40 (t, J=8.08 Hz, 1 H) 11.31 (br. s., 1 H).

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

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, molecular formula is C7H6BrFO, 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. Recommanded Product: 446-59-3

2-Bromo-3-fluoro anisole (10 g, 48.77 mmol) was dissolved in DCM (200 mL) and cooled to about -78 C. To the solution was added BBr3 (11.53 mL, 121.9 mmol) in one portion. The mixture was warmed to r.t. and stirred overnight. The mixture was partitioned between water and DCM (50 mL), and the aqueous layer was back extracted with DCM (200 mL). The combined organics were dried (NaSO4), filtered and concentrated to give about 9.32 g of the product as a dark oil. MS found 188.9 (M-1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 446-59-3, its application will become more common.

Reference:
Patent; Briner, Karin; Doecke, Christopher William; Mancuso, Vincent; Martinelli, Michael John; Richardson, Timothy Ivo; Rothhaar, Roger Ryan; Shi, Qing; Xie, Chaoyu; US2004/82590; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 36865-41-5, 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. 36865-41-5, name is 1-Bromo-3-methoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of 33b (0.68 g, 1.74 mmol) and K2CO3 (322 mg, 2.33 mmol) in DMF (15 mL) was added 2-chloro-N,N-diethylacetamide (0.31 g, 2.07 mmol) and the mixture was stirred at room temperature for 2 h, at 50 C for 30 min, and at 80 C for 1 h. Then, additional 2-chloro-N,N-diethylacetamide (0.30 g, 2.01 mmol) was added to the mixture, which was stirred at 80 C for additional 30 min. After being cooled to room temperature, the reaction was acidified with 1 M HCl, and extracted with EtOAc, and the combined organic layer was washed with sat. NaHCO3 and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-EtOAc, 9:1 to 1:2) to give crude 7c (1.39 g, quant.) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-methoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Article; Rikimaru, Kentaro; Wakabayashi, Takeshi; Abe, Hidenori; Tawaraishi, Taisuke; Imoto, Hiroshi; Yonemori, Jinichi; Hirose, Hideki; Murase, Katsuhito; Matsuo, Takanori; Matsumoto, Mitsuharu; Nomura, Chisako; Tsuge, Hiroko; Arimura, Naoto; Kawakami, Kazutoshi; Sakamoto, Junichi; Funami, Miyuki; Mol, Clifford D.; Snell, Gyorgy P.; Bragstad, Kenneth A.; Sang, Bi-Ching; Dougan, Douglas R.; Tanaka, Toshimasa; Katayama, Nozomi; Horiguchi, Yoshiaki; Momose, Yu; Bioorganic and Medicinal Chemistry; vol. 20; 10; (2012); p. 3332 – 3358;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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 solution of amine (1 mmol) in 3 mL of pyridine at 0¡ãC was slowly added the appropriate benzenesulfonyl chloride (1.1 mmol, 1.1 equiv). The mixture was stirred for 12 h at 25¡ãC. The mixture was quenched with 2N HCl, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated in vacuum. The crude product was purified by recrystallization and/or chromatography as noted below.

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

Reference:
Article; Kril, Liliia M.; Vilchez, Valery; Jiang, Jieyun; Turcios, Lilia; Chen, Changguo; Sviripa, Vitaliy M.; Zhang, Wen; Liu, Chunming; Spear, Brett; Watt, David S.; Gedaly, Roberto; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 3897 – 3899;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 886762-08-9 as follows. Computed Properties of C7H5BrF3NO

10.74 g (93.75 mmol) of tert-butyl nitrite and 28.5 g (150 mmol) of copper iodide are suspended in 270 ml of acetonitrile and heated to 60 C. A solution of 15 g (62.5 mmol) of 5-bromo-2-trifluoromethoxyaniline in 130 ml of acetonitrile is slowly added dropwise to this suspension and the mixture is left to stir at 60 C. for another hour. The reaction solution is then poured on to a mixture of 250 ml of 2 N aqueous HCl and 250 ml of ethyl acetate. The organic phase is washed twice more with aqueous NaCl solution, filtered through a little silica gel and concentrated. The residue is separated by chromatography on silica gel (ethyl acetate/n-heptane=1/18). This affords 12.2 g (52% yield) of product 96 as a colorless oil.

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2011/59910; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. Product Details of 651734-54-2

A mixture of intermediate 11 (1.4g; 4.6 mmol), 2,6-difluoro-3,5-dimethoxyaniline (1.4 g;7.3 mmol), Brettphos palladacycle (0.18 g; 0.23 mmol) and cesium carbonate (4.5 g; 14mmol) in toluene (60 mL) was heated at 100 00 overnight. The mixture was cooled, poured onto cooled water and EtOAc was added. The solution was filtered through a pad of Celite (diatomaceous earth) and the product was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to dryness.The residue (2.6 g) was purified by chromatography over silica gel (irregular SiOH,300 g; mobile phase: 60% heptane, 5% MeOH, 35% EtOAc). The fractions containingthe product were collected and evaporated to dryness yielding 1.1 g of an intermediatewhich was crystallized from Et20 yielding 1.06 g (56 %) of intermediate 22.MP = 214C (DSC)

The synthetic route of 651734-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; ANGIBAUD, Patrick Rene; QUEROLLE, Olivier Alexis Georges; PILATTE, Isabelle Noelle Constance; MEERPOEL, Lieven; PONCELET, Virginie Sophie; WO2014/174307; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 702-24-9, These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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.

N-(4-Methoxybenzyl)-N-methylamine (78 muL, 0.5 mmol),And a stirrer is placed in the reaction tube,After replacing the inert gas, DMF (193 muL, 2.5 mmol) was added, and the reaction tube was sealed.The reaction tube was placed in a 150 ¡ã C oil bath reaction pot.The reaction was stirred for 96 hours.After cooling to room temperature, it was diluted with 15 mL of water and extracted with ethyl acetate three times, 15 mL each time.The combined extracts were dried over anhydrous sodium sulfate and filtered and evaporated.The crude product was subjected to column chromatography using ethyl acetate: petroleum ether = 1:2 (1percent triethylamine) as eluent.Yellow oil, yield 99percent.

Statistics shows that 4-Methoxy-N-methylbenzylamine is playing an increasingly important role. we look forward to future research findings about 702-24-9.

Reference:
Patent; Xiangtan University; Gong Xing; Yin Jiawen; Cai Changqun; (15 pag.)CN109293569; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 24332-20-5, These common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, 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.

Example 9 A flask was charged with methoxyacetaldehyde dimethylacetal (1.2 equiv.), trifluoroacetic acid (1.3 equiv.), and water (equal volume to TFA), and the mixture was stirred at 50 C for 10 min. The reaction mixture was then removed from the heating bath and TEA (1.3 equiv.) was added followed by a solution of 3-(N-Boc-aminomethyl)-azetidine (1 equiv.) in EtOH and DCM, and then NaBH(OAc)3 (3 equiv.). The reaction was stirred for 12 hrs at 20 C. The reaction mixture was extracted and distilled to remove some ethanol. To the organic layer was added 5M HCl in iPrOH (7 equiv.) at 50 C. TBME was added at 48 C over 45 min, and cooled to 20 C over 60 min. The reaction stirred for another 60 min, filtered, and the filter cake was washed with TBME. The organic layer was dried to provide 1 -(2-methoxyethyl)-3-(methylamino)-azetidine dihydrochloride.

Statistics shows that 1,1,2-Trimethoxyethane is playing an increasingly important role. we look forward to future research findings about 24332-20-5.

Reference:
Patent; SATORI PHARMACEUTICALS, INC.; BRONK, Brian, Scott; AUSTIN, Wesley, Francis; CREASER, Steffen, Phillip; FULLER, Nathan, Oliver; HUBBS, Jed, Lee; SHEN, Ruichao; WO2013/36665; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem