Tag: M.W=100-200

366-99-4, name is 3-Fluoro-4-methoxyaniline, 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. Product Details of 366-99-4

Cyanuric chloride (11.07 g, 60 mmol) was dissolved in 40 mL CH3CN and was cooled to about -20¡ã C. To this was added DIEA (11.5 mL, 60 mmol) followed by 3-fluoro-4-methoxyaninline (8.47 g, 60 mmol) in 20 mL CH3CN (reaction froze). The reaction was allowed to warm to room temperature after about 1 hour at -20¡ã C. TLC (2percent CH3OH/CH2Cl2) and mass spectroscopy indicated the presence of the compound 124. The reaction mixture was cooled to about 0¡ã C. before adding DIEA (11.5 mL, 66 mmol). 2-Aminomethyl-1-ethylpyrrolidine (7.77 g, 60 mmol) in CH3CN (10 mL) was added. The reaction was allowed to warm to rt and stirred overnight. Then DIEA (11.5 mL, 66 mmol) and S-(+)-2-methoxyethylpyrrolidine (6.91 g, 60 mmol) in 20 mL 1,4-dioxane were added. The reaction was heated at about 50¡ã C. overnight. The solvent was removed in vacuo, and the resulting residue was purified by flash chromatography on silica gel packed in ethyl acetate. The front running impurities were removed and subsequently the eluent was increased in polarity to 10percent CH3OH:ethyl acetate. The material collected from the column was then dissolved in water and extracted in CH2Cl2 (4 times), dried over MgSO4, and concentrated to dryness to give a brown solid 145 (9.7 g, 27.6percent yield), 71-72¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 5.37 min, 90.3percent purity; 1H NMR (600 MHz, CDC3, 55¡ã C.) delta 7.69 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.86 (t, J=9 Hz, 1H), 4.29 (s, 1H), 3.90-3.96 (m, 1H), 3.84 (s, 3H), 3.63-3.81 (m, 6H), 3.35 (s, 3H), 3.23-3.25 (m, 1H), 2.85 (broad s, 1H), 2.78 (broad s 1H), 2.14 (broad s, 2H), 1.89-2.04 (m, 6H), 1.37 (apparent t, J=7.2 Hz, 3H); 13C NMR (150.8 MHz, CDCl3, 55¡ã C.) delta 165.8, 163.8 (2C), 152.3 (d, Jc-f=243.5 Hz), 143.0 (142.9, rotamer or diastereumer), 133.7 (133.67, rotamer or diastereomer), 115.0, 114.4, 109.1 (108.9, rotamer or diastereomer), 72.8, 66.6, 59.0, 57.0, 56.6, 53.7, 51.0, 46.8, 42.2, 28.4 (28.2, rotamer or diastereomer), 23.1 (23.0, rotamer or diastereomer), 10.9; MS (ESI) mn/z 460.2 (M+H, 44.7), 251.1 (47.7), 235.1 (27.5), 231.1 (37.4), 230.6 (100), 214.6 (36.5).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
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Related Products of 645-36-3, 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. 645-36-3 name is 2,2-Diethoxyethanamine, 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.

A mixture of 2-bromo-5,6-dihydro-4H-pyrazolo[1,5-d][1,4]diazepine-7(8H)-thione (265.0 mg, 1.07 mmol), 2,2-diethoxyethan-1-amine (1.42 g, 10.7 mmol) and silver carbonate (590 mg, 2.14 mmol) in tetrahydrofuran (10 mL) was stirred at 80 C. for 1 h. The solvent was concentrated under vacuum. The residue was purified by reverse-phase column eluting with water (0.05% TFA)/CH3CN (85/15) to afford 2-bromo-N-(2,2-diethoxyethyl)-5,8-dihydro-4H-pyrazolo[1,5-d][1,4]diazepin-7-amine (295 mg, 80%) as a brown oil. LCMS (ESI) [M+H]+=345.0.

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

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 39538-68-6, name is 2-Methoxy-4-methylaniline, 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 39538-68-6, Recommanded Product: 2-Methoxy-4-methylaniline

To a test tube with a magnet stirrer bar was added N-methyl-2-{[2-(1 /-/-1 , 2, 4-triazol-1 – yl)-5- (trifluoromethyl) pyrimidin-4-yl] amino} benzamide (Compound 6, 0.200 g, 0.550 mmol) and 2-methoxy-4-methyl aniline (0.083 g, 0.606 mmol, 1 .1 eq.). To the mixture, trimethylacetic acid (1 .0 g, 9.791 mmol, 17.8 eq.) was added and the resulting suspension was stirred and heated in an oil bath set at 130 C. The progress of the reaction was monitored by HPLC. After 29 h the reaction mixture was cooled to room temperature, quenched with 3 N NaOH (3.9 ml_, 1 1 .75 mmol, 21 eq.) and diluted with toluene. Insoluble solids were filtered off and the layers were separated. The organic phase was washed with water and brine and then concentrated under vacuum. The residue was stirred in a mixture of heptanes and dichloromethane at room temperature and the resultant solids were collected by filtration and rinsed with heptane. The damp solid was dried under high vacuum to give 1 18 mg of the desired product as a pale solid. 1 H NMR {CDCI3}: 5(ppm) 10.75 (br s, 1 H, NH), 8.46 (d, J = 8.0 Hz, 1 H, ArH ), 8.36 (s, 1 H, ArH), 8.14 (d, J = 8.0 Hz, 1 H, ArH), 7.64 (br s, 1 H, NH), 7.45 – 7.49 (m, 2 H, 2X ArH), 7.13 (t, J = 8.0 Hz, 1 H, ArH), 6.72 (s, 1 H, ArH), 6.68 (d, J = 8.0 Hz, 1 H, ArH), 6.18 (br s, 1 H, NH), 3.88 (s, 3 H, OCH3), 3.02 (d, J = 4.0 Hz, 3 H, NCH3), 2.34 (s, 3 H, CH3). 19F NMR {CDC }: 5(ppm) 61 .4. HPLC: 97.2% area, Rt = 7.34 min.

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-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; CASTELHANO, Arlindo L.; RECHKA, Josef A.; SENANAYAKE, Chandrawansha; DEVANATHAN, Krishnaswamy; GNANAVELU, Karunanidhi; WO2014/126954; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 767-91-9, name is 2′-Methoxyphenyl acetylene, 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 767-91-9, SDS of cas: 767-91-9

General procedure: A dried Schlenk tube equipped with a magnetic stir bar was charged with the alkyne (1mmol), organic azide (1mmol), and Cu(PPh3)2NO3 (0.005mmol, 3.28mg). The mixture was stirred at rt (rt was ?25C) without exclusion of air under solvent-free conditions. After the reaction was completed, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to obtain the crude product that was further purified by silica gel chromatography (petroleum ether/ethyl acetate (20: 1) as eluent) to yield the corresponding deuterated triazoles.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Wang, Dong; Chen, Si; Wang, Jing; Astruc, Didier; Chen, Baohua; Tetrahedron; vol. 72; 41; (2016); p. 6375 – 6379;,
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Some common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, molecular formula is C4H9BrO, 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-Bromo-2-ethoxyethane

General procedure: To a mixture of 1,2,4-triazole 1 (1 mmol), triethylamine (1.1 mmol)and ethanol (20 ml) was added with stirring bromoethanol (2), chloropropanol(3), chloroglycerol (4), 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (5), bromoethylmethyl ether (6) and/or bromoethylethylether (7) (1.1 mmol). The mixture was stirred at reflux for8 h with 2-4 and for 6 h with 5-7. Ethanol was removed under pressureand the resulting solid was collected and recrystallized from ethanol toafford the targeted S-acyclonucleoside analogues 8-13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 592-55-2, its application will become more common.

Reference:
Article; Aouad, Mohamed Reda; Al-Mohammadi, Hannan Musallam; Al-blewi, Fawzia Faleh; Ihmaid, Saleh; Elbadawy, Hossein Mostafa; Althagfan, Sultan Saad; Rezki, Nadjet; Bioorganic Chemistry; vol. 94; (2020);,
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Electric Literature of 6346-09-4, A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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.

Hexahydroindolizin-7(1H)-one (140): Prepared according to WO0000487A1, U.S. Pat. No. 5,874,427, WO0017198A1.

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; Maddaford, Shawn; Ramnauth, Jailall; Rakhit, Suman; Patman, Joanne; Renton, Paul; Annedi, Subhash C.; US2006/258721; (2006); A1;,
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Application of 74654-07-2, 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. 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Benzhydryl 2-chloroethyl ether (2 mmol) and mPEGn-NH2 (3 mmol) were dissolved in 10 ml of acetonitrile, and then sodium hydroxide (2 mmol) in water (1 mL) was added to the solution. The mixture was stirred at 100 C for 16 hours. Dichloromethane (200 ml) was added to the reaction mixture, and the resulting solution was washed with water (200 mL x 3). The organic phase was dried and solvent was removed under reduced pressure. The crude product was purified by column chromatography (SiO2: DCM/CH3OH, 20:1) or alternatively using flash chromatography on silica gel using CAN/H2O (40M C-18RP column, Biotage, Inc., Charlottesville, VA). The desired product of mPEGn-NH- diphenhydramine obtained in -70% yield and mPEGn-N-(diphenhydramine)2 was also obtained in 15% yield.

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

Reference:
Patent; NEKTAR THERAPEUTICS AL, CORPORATION; WO2008/112257; (2008); A1;,
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Application of 658-89-9, 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. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 18 (SV2-Nitro-6-f4-(5-trifluoromethoxy-1H-benzoimida2ol-2-yl)-benzyloxy1 -6.7-dihvdro-5H-imidazor2.1-bin .3l oxazine (23)23In an inert atmosphere, 4-((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b)[1 ,3]oxazin-6- yloxymethyl)-benzoic acid (100 mol%) is dissolved in anhydrous CH2CI2 (0.20 M) and added HATU (120 mol%) and DIEA (120 mol%). Reaction is stirred at room temperature for 5 min followed by addition of 1,2-diamino-substituted benzene (120 mol%). Resulting reaction mixture is stirred at room temperature overnight. Reaction is concentrated and dissolved in EtOAc and washed with water three times. Organic layer is dried under anhydrous Na2SO4 and concentrated to yield pale brown solid, which is dissolved in glacial acetic acid (0.36 M). Reaction mixture is heated to 95 ‘C for 30 min. Crude reaction mixture is concentrated and residue obtained is purified by preparative reverse-phase LC to give final compound as fluffy solid. MS: M+ 476.4.1H NMR (CD3OH1 400 MHz): delta 8.05 (d. J = 8.18 Hz, 2H), 7.74 (s, 1 H), 7.62 (d, J = 8.76 Hz, 1H), 7.50 (m, 3H)1 7.18 (dd, J = 8.73, 1.24 Hz, 1H), 4.87 (s, 2H)1 4.73 (m, 2H)1 4.48 (d, J = 12.05 Hz, 1H), 4.30 (m, 2H). Melting Point: 98-99 ‘C. [Q]21D = -37.81 (C= 0.003, MeOH).

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-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; US DEPARTMENT OF HEALTH & HUMAN SERVICES; WO2007/75872; (2007); A2;,
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Some common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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: C8H7F3O

A solution of n-butyllithium (20.4 mL, 51.1 mmol) and TMEDA (9.00 mL, 59.6 mmol) in anhydrous THF (50 mL) was cooled to -78 C. 1-Methoxy-3-(trifluoromethyl)benzene (1) (10 g, 57 mmol) was added dropwise and the reaction mixture was stirred at -78 C. for 15 min then allowed to warm to RT and stirred for 10 min. The reaction mixture was cooled to -78 C. and trimethyl borate (16.1 mL, 142 mmol) was added slowly, dropwise, and the reaction mixture was stirred at -78 C. for 15 min then allowed to warm to RT and stirred for 20 h. 7N NH3/MeOH (20 mL) was added and the solvent was removed in vacuo. The residue was dissolved in formic acid (20 mL) and cooled to 0 C. before hydrogen peroxide (6.00 mL, 68.5 mmol) was added and the solution was allowed to warm to RT and stirred for 2 h. The product was extracted with EtOAc (3*50 mL), and then the combined organics were shaken with NaOH (2*50 mL). The aq phase was acidified with 1M HCl and the product was extracted with DCM (2*30 mL). The organic solution was washed with brine (2*30 mL), dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (120 g, 0-5% MeOH in DCM) to afford 2-methoxy-6-(trifluoromethyl)phenol (2) (4.95 g, 45%) as a colourless oil: m/z 191 [M-H]- (ES-); 1H NMR (400 MHz, CDCl3) delta: 7.15-7.09 (1H, m), 7.04-6.98 (1H, m), 6.89 (1H, td), 6.14 (1H, br s), 3.91 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 454-90-0, its application will become more common.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, 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 6851-80-5, COA of Formula: C9H13NO

General procedure: To a mixture of the corresponding secondary amines 14A-F (0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) and KI (8.6 mg, 0.052 mmol) in anhydrous CH3CN (12 ml) were added the appropriate intermediates 10-13 (0.5 mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water (40 mL) and the mixture was extracted with dichloromethane (25 mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of CH2Cl2/CH3OH (100:1) as eluent to afford the corresponding scutellarein-O-alkylamine derivatives 15-18.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 – 366;,
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