Month: September 2021

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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6F12O2

In a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel, and a reflux condenser (anhydrous calcium chloride at the top),Add 1,3-dimethyl-1,3,5-triazine (2.76 g, 24 mmol)And dichloromethane (30 mL),After stirring to dissolve, add triethylamine (3.25mL, 26mmol) and cool to 0 C.Was added dropwise with stirring hexafluoropropylene oxide dimer (6.64g, 20mmol),After 1 hour, the addition was completed. After the addition, the reaction was stirred at 0 C for 3 hours.The reaction mixture was washed with 10% sodium hydroxide solution (50 mL) and separated. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was spin-dried.The residue was separated and purified by column chromatography [dichloromethane / methanol (v / v) = 20/1],7.86 g of a colorless transparent liquid fluorinated intermediate I-1 were obtained,Yield: 92%.

The synthetic route of 2062-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ruyuan Dongyang Guangfu Co., Ltd.; Li Yitao; Lan Xiaobin; Hou Qinqing; Yang Feng; Jia Yuan; Cheng Zhen; (9 pag.)CN110818650; (2020); A;,
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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 109-85-3 as follows. name: 2-Methoxyethylamine

Ligand 1b was prepared according to the method described for 1a using 2-(methoxy)ethylamine (0.39 mL, 4.54 mmol) and 1- methyl-1H-imidazole-2-carbaldehyde (0.455 g, 4.13 mmol) and isolated as a pale yellow oil in 92% yield. 1H NMR (300 MHz, CD2Cl2): d(ppm) 8.26 (s, 1H), 7.04 (s, 1H), 6.94 (s, 1H), 3.95 (s, 3H), 3.75e3.68 (m, 2H), 3.67e3.60 (m, 2H), 3.33 (s, 3H). 13C{1H} NMR (75 MHz, CD2Cl2): d(ppm) 154.96, 143.59, 129.32, 125.12, 72.53, 61.64, 58.86, 35.46. FT-IR (cm 1): 2875m, 1650s (nC]N), 1518w, 1475m, 1437m, 1366w, 1287m, 1236w, 1191w, 1118s, 1026w, 955w, 919m, 802m, 757m, 708m, 690m, 558w, 473w.

According to the analysis of related databases, 109-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Boudier, Adrien; Breuil, Pierre-Alain R.; Magna, Lionel; Olivier-Bourbigou, Helene; Braunstein, Pierre; Journal of Organometallic Chemistry; vol. 718; (2012); p. 31 – 37,7;; ; Article; Boudier, Adrien; Breuil, Pierre-Alain R.; Magna, Lionel; Olivier-Bourbigou, Helene; Braunstein, Pierre; Journal of Organometallic Chemistry; vol. 718; (2012); p. 31 – 37;,
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Reference of 4342-46-5, 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. 4342-46-5, name is 4-Methoxycyclohexanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 0.25 g (0.793 mmol) of 2,6-Difluoro-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile in DMSO (5 mL) was added 0.225 g (1.7446 mmol) DIEA and 0.186 g (1.438 mmol) of crude 4-Methoxy-cyclohexylamine. This was stirred at 100 C. for 18 hours and then poured into 25 mL water and extracted 3 times with CH2Cl2. The organic layers were dried over Na2SO4, concentrated and purified via chromatography (50% EtOAc/Hex) to give 0.163 g of 2-Fluoro-6-(4-methoxy-cyclohexylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile (48.5% yield). LCMS (m/z): M+H=425.2.

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

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
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Reference of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 1,4-bis(bromomethyl)benzene (1 mmol) in anhydrous acetonitrile (10 mL) was added potassium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 3 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (150:1, v/v) to give the title compound as a colorless liquid or a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Liu, Shuangping; Gaines, Theresa; Oum, Yoonhyeun; Shi, Qi; Mooring, Suazette Reid; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 340 – 350;,
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Application of 6487-99-6, These common heterocyclic compound, 6487-99-6, name is 2-(3-Methylphenoxy)ethylamine, 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.

A solution of Example IB (25 mg, 0.08 mmol) in N,N-dimethylformamide (1.0 mL) was treated with a solution of 2-(3H-[l ,2,3]triazolo[4,5-]pyridin-3-yl)- l, 1 ,3,3- tetramethylisouronium hexafluorophosphate(V) (35 mg, 0.09 mmol) in N,N-dimethylformamide (0.5 mL). Then a solution of 2-(m-tolyloxy)ethanamine (12 mg, 0.08 mmol) in N,N- dimethylacetamide (0.15 mL) was added followed by N,N-diisopropylethylamine (0.037 mL, 0.21 mmol). The reaction was shaken at ambient temperature overnight and purified by HPLC (2-coupled C8 5 mupiiota 100 A columns 30 mm x 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid in water)) to provide the title compound. JH NMR (400 MHz, DMSO-Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
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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. 450-88-4 name is 1-Bromo-4-fluoro-2-methoxybenzene, 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. 450-88-4

Intermediate Example Int20.014-(4-bromo-3-methoxyphenoxy)-1 -methylpiperidine To a stirred suspension of sodium hydride (1.76 g; 60% w/w sodium hydride in oil) in DMF (55 mL) was added 1 -methylpiperidin-4-ol (3.37 g) at 0 C. The mixture was stirred at room temperature for 30 minutes. 1 -bromo-4-fluoro-2- methoxybenzene (3.0 g) was added and the mixture was stirred at 100 C for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica- gel chromatography gave 3.65 g of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philip; WENGNER, Antje Margret; BRIEM, Hans; HOLTON, Simon; SIEMEISTER, Gerhard; PRECHTL, Stefan; KOPPITZ, Marcus; STOeCKIGT, Detlef; PRIEN, Olaf; WO2011/157688; (2011); A1;,
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Synthetic Route 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.

The 15.0g of 3-amino-1-methoxy-2-methyl, 48.7g of triphosgene and 350 ml of toluene in a mixture of the heating to reflux with stirring 3 hours. Cooling the reaction mixture, the concentrated under reduced pressure, to obtain 17.0g of 1-methoxy-3-isocyanato-2-methylbenzene (called below 4A).

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; Sumitomo Chemical Co., Ltd.; Takayuki, Shiota; Masaki, Arimori; (241 pag.)CN105492432; (2016); A;,
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Reference of 31576-51-9,Some common heterocyclic compound, 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, molecular formula is C5H13NO2, 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 4-thioxo-l, 3-thiazolidin-2-one (2.24 g) in ethanol (20 mL) was added 2- (2-methoxyethoxy) ethanamine (2.5 g), and the mixture was stirred at room temperature for 5 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(ethyl acetate) to give the title compound (3.1 g) .XH NMR (300 MHz , CDC13) delta 3.43 (3H, s) , 3.48-3.63 (2H, m) , 3.63-3.83 (6H, m) , 4.13 (2H, s) , 6.83 (1H, brs) .MS (ESI+) : [M+H]+ 219.1.

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-Methoxyethoxy)ethanamine, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MATSUMOTO, Shigemitsu; ONO, Koji; TOMINARI, Yusuke; KATOH, Taisuke; MIWA, Kazuhiro; HASUOKA, Atsushi; IMAMURA, Shinichi; WO2013/18929; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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 29578-83-4, Computed Properties of C8H9BrO

Add 1-bromo-3-methoxy-5-methylbenzene 4a (22.8 g, 113 mmol) to the eggplant-shaped bottle, and dissolve in methylene chloride (100 mL) Add N-bromosuccinimide (242 g, 136 mmol) and azobisisobutyronitrile (31.5 g, 192 mmol) and heat to 45 C under reflux overnight. After the reaction is over,The reaction was returned to room temperature and extracted with ethyl acetate (40 mL x 3).The organic phase was washed with water (40 mL x 2) and brine (40 mL * 2),It was then dried over anhydrous sodium sulfate, filtered and concentrated.The obtained crude product was separated by a normal-phase silica gel column (petroleum ether: ethyl acetate = 20: 1) to obtain 1-bromo-3-(bromomethyl)-5-methoxybenzene 4b (20 g, yellow solid), yield : 63%.

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:
Patent; Shanghai Meidixi Bio-pharmaceutical Co., Ltd.; Meidixipuya Pharmaceutical (Shanghai) Co., Ltd.; Ren Feng; Wang Xianlian; Xu Yongmei; Chen Chunlin; Cai Jinna; (28 pag.)CN110194773; (2019); A;,
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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. Computed Properties of C7H8FNO

Cyanuric chloride (11.07 g, 60 mmol) was dissolved in 40 mL CH3CN and was cooled to about -20° 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° C. TLC (2percent CH3OH/CH2Cl2) and mass spectroscopy indicated the presence of the compound 124. The reaction mixture was cooled to about 0° 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° 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° 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° 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° 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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