Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, belongs to nitriles-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 1813-33-8, 1813-33-8

To commercially available 2-chloro-4-trifluoromethylbenzonitrile 13 (lml, 7.2 mmol) pyrrolidine (4equiv., 2.38 ml) was added and the solution was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 940mg of a yellow solid. Yield = 54% ‘HNMR (DMSO, 200 MHz) delta 1.95 (4H, m), 3.58 (4H, m), 6.94 (2H, m), 7.73 (1H, dd, J = 8 Hz, J’= 0.8 Hz).

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-Chloro-4-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); 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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, This compound has unique chemical properties. The synthetic route is as follows., 52133-67-2

To a microwave reaction tube was charged with 37 (1.1 g, 5.0 mmol), 2-cyano-4,4- diethoxy-butyric acid ethyl ester (1.7 g, 7.4 mmol) and NaOMe (25percent by wt in MeOH; 10 mL). The reaction tube was sealed and the solution irradiated with microwave at 150 0C for 30 min. After cooling to room temperature, the mixture was concentrated. The residue was taken up in water (10 mL) and the pH adjusted to 1 with 6M of HCl. The resulting solution was stirred at room temperature for 25 min and then the pH adjusted to 9 with concentrated NH4OH. The resulting solid was filtered, washed with water and dried under high vacuum to afford the title compound as a grey solid (1.5 g, 94percent). The material was used in the next step without purification.[0234] 1H NMR (500 MHz, DMSO-J6) delta 2.25 (s, 3H), 5.07 (s, 2H), 6.29 (dd, J = 3.0, 2.2 Hz, IH), 6.75 (t, J = 2.7 Hz, IH), 6.76 (d, J = 0.7 Hz, IH), 7.09-7.15 (m, 3H), 7.60 (d, J = 8.5 Hz, 2H), 8.71 (s, IH), 10.28 (br s, IH), 11.36 (s, IH) MS (ES+): m/z 321 (M+H)+

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; TARGEGEN INC.; WO2009/49028; (2009); 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. 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., 328-87-0

(a) Preparation of 3-(2-cyano-4-trifluoromethylphenoxy)benzoic acid 3-Hydroxybenzoic acid (27.6 g), 4-chloro-3-cyano-benzotrifluoride (41.1 g) and anhydrous potassium carbonate (55.2 g) were stirred together for 71/2 hours at 100 C. in dry dimethylformamide (500 ml) and then left at room temperature for 65 hours. The solvent was then removed under reduced pressure and the residue taken up in water and acidified with dilute hydrochloric acid. The solid which separated was washed with water, dissolved in ether and the solution dried and concentrated. The colourless solid which separated was recrystallized to give the benzoic acid derivative (24.0 g) with a melting point of 224-226 C.

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; Imperial Chemical Industries Limited; US4285723; (1981); A;,
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52133-67-2, 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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Method AJ: 2-(Pyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol (xliii) To a solution of nicotinimidamide (5.03 g, 41.6 mmol, 1.2 eq.) in EtOH (100 mL), was added NaOMe (4.8 g, 88.8 mmol, 2.5 eq.). The mixture was stirred at room temperature for 4 h. The reaction mixture was added to ethyl 2-cyano-4,4-diethoxybutanoate (8.00 g, 34.9 mmol, 1 eq.). This mixture was stirred at 105¡ã C. overnight. After cooling, the reaction mixture was acidified with conc. HCl and stirred at room temperature for 2 h. A precipitate formed and was collected and washed with H2O (20 mL*2). After lyophilization, 3.10 g of product was obtained as a gray yellow solid (yield 41.8percent). LCMS m/z=213.1 (M+1) (Method B) (retention time=1.07 min). 1H NMR (400 MHz, DMSO-d6): delta 12.26 (s, 1H), 12.04 (s, 1H), 9.23 (d, J=1.6 Hz, 1H), 8.70 (dd, J=4.8, 1.2 Hz, 1H), 8.43-8.40 (m, 1H), 7.55 (dd, J=8.0, 4.8 Hz, 1H), 7.12 (d, J=1.6 Hz, 1H), 6.51 (d, J=2.8 Hz, 1H).

The synthetic route of Ethyl 2-cyano-4,4-diethoxybutyrate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzuki, Masaki; Kondo, Kazumi; Kurimura, Muneaki; Valluru, Krishna Reddy; Takahashi, Akira; Kuroda, Takeshi; Takahashi, Haruka; Fukushima, Tae; Miyamura, Shin; Ghosh, Indranath; Dogra, Abhishek; Harriman, Geraldine; Elder, Amy; Shimizu, Satoshi; Hodgetts, Kevin J.; Newcom, Jason S.; US2015/307477; (2015); A1;,
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179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, belongs to nitriles-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. 179898-34-1

A solution of 3-bromo-5-fluorobenzonitrile (2.5g, 12.5mmol), (trimethylsilyl)acetylene(2.86ml,20mmol), bis(acetate)bis(triphenylphoshpino)Palladium(II) (936mg, 1.25mmol) and triethylamine (35ml) in toluene (35ml) was degassed by bubbling nitrogen through the solution and then stirred at 950C for 30 minutes. Filtration and concentration to yield a crude product. It was diluted with EtOAc (150ml). The organic phase was washed with saturated NaHCO3 solution (50ml), brine (50ml) and the organic layer was dried over sodium sulfate. Filtration EPO and concentration to yield a product A293.1 (2Ag, 88%). HPLC: 95%, retention time: 4.05 minute (condition A). LC/MS (M+H)+ = 218.2.

Statistics shows that 179898-34-1 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-fluorobenzonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
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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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, A new synthetic method of this compound is introduced below., 1835-65-0

SYNTHESIS EXAMPLE 6 Synthesis of 3-(2,6-dimethylphenoxy)-4,5-bis(phenylthio)-6-fluorophthalonitrile In a four-neck separable flask having an inner volume of 500 ml, 60 g (0.30 mol) of tetrafluorophthalonitrile, 41.8 g (0.72 mol) of potassium fluoride, and 160 ml of acetone were placed. Further, in a dropping funnel attached thereto, 33.0 g (0.60 mol) of thiophenol was charged. The thiophenol from the dropping funnel was added dropwise from the dropping funnel while kept stirred, with the speed of dropping adjusted so as to keep the reaction temperature of not more than 40¡ã C. and the stirring was subsequently continued for about two hours. Then, to this flask, 40.3 g (0.33 mol) of 2,6-dimethylphenol, 20.9 g (0.36 mol) of potassium fluoride, and 40 ml of acetonitrile were charged. The mixture was kept stirred under reflux for 8 hours. The reaction solution was cooled and filtered. The filtrate was washed with 600 ml of acetonitrile and filtered. The combined filtrate was distilled by a rotary evaporator to expel the acetonitrile and was recrystallized from methanol. The produced crystals were separated by filtration and vacuum dried to afford 113.8 g of 3-(2,6-dimethylphenoxy)-4,5-bis(phenylthio)-6-fluorophthalonitrile (yield: 78.6 mol percent).

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; Nippon Shobukai Co., Ltd.; US6323340; (2001); B1;,
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179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

824 mg (0.900 mmol) of tris(dibenzylideneacetone)dipalladium and 1.23 g (1.98 mmol) of rac-1,1′-binaphthalene-2,2′-diylbis(diphenylphosphane) are added to 9.00 g (45.0 mmol) of 3-bromo-5-fluorobenzenecarbonitrile in toluene (300 ml) under an argon atmosphere. After the addition of 19.5 g (54.0 mmol) of (1-ethoxyvinyl)tributylstannane, the mixture is stirred under reflux overnight. The reaction mixture is subsequently concentrated and the residue is taken up in 300 ml of THF. After the addition of 100 ml of an aqueous 2N hydrogen chloride solution the mixture is stirred at room temperature for 2 h. The reaction mixture is subsequently neutralized with a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 9:1). 7.11 g (97% of theory) of the title compound are obtained.1H-NMR (400 MHz, DMSO-d6): delta=8.28 (t, 1H), 8.18-8.14 (m, 1H), 8.08-8.04 (m, 1H), 2.65 (s, 3H).GC-MS (Method 11): Rt=3.97 min; MS (EIpos): m/z=163 [M]+.

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AiCuris GmbH & Co. KG; US2011/124618; (2011); A1;,
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79463-77-7, name is Diphenyl N-cyanocarbonimidate, belongs to nitriles-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. 79463-77-7

To a solution of heptadecan-9-yl 8-((3-aminopropyl)(8-(nonyloxy)-8- oxooctyl)amino)octanoate (220 mg, 0.3 mmol) in 5 mL 2-propanol was added triethylamine (0.04 mL, 0.3 mmol) followed by diphenyl cyanocarbonimidate (72 mg, 0.3 mmol) and the mixture stirred at rt for two hours. To the reaction mixture was added a 2M dimethylamine solution in THF (0.75 mL, 1.5 mmol) and the resulting solution heated to 75 C for 18 hours. Additional 2M dimethylamine/THF solution (0.75 mL, 1.5 mmol) was added and the temperature increased to 85 C. After six hours the reaction was complete by LC/MS so the solution was reduced under vacuum, diluted with DCM and washed once with a saturated aqueous sodium bicarbonate solution. The organic phase was dried (MgSC^), filtered and the filtrate evaporated in vacuo. The residue was purified by silica gel chromatography (0-50% (mixture of 1 % NH4OH, 20% MeOH in dichloromethane) in dichloromethane) to give heptadecan-9-yl (Z)-8-((3-(2-cyano-3,3-dimethylguanidino)propyl)(8-(nonyloxy)-8- oxooctyl)amino)octanoate (119.2 mg, 0.14 mmol, 49%) as a colorless syrup. UPLC/ELSD: RT = 3.52 min. MS (ES): m/z (MH+) 819.0 for C49H95N5O4. XH NMR (300 MHz, CDC13) delta: ppm 7.62 (br. s., 1H); 4.86 (quint, 1H, J = 6 Hz); 4.05 (t, 2H, J = 7.5 Hz); 3.68 (d, 2H, J= 3 Hz); 2.99 (s, 6H); 2.59 (br. s, 2H); 2.43 (br. s, 3H); 2.28 (m, 4H); 1.71 (br. s, 2H); 1.62 (m, 8H); 1.49 (m, 5H); 1.26 (br. m, 50H); 0.88 (t, 9H, J = 7.5 Hz).

Statistics shows that 79463-77-7 is playing an increasingly important role. we look forward to future research findings about Diphenyl N-cyanocarbonimidate.

Reference:
Patent; MODERNATX, INC.; BENENATO, Kerry, E.; KUMARASINGHE, Ellalahewage, Sathyajith; CORNEBISE, Mark; (305 pag.)WO2017/49245; (2017); A2;,
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179898-34-1, The chemical industry reduces the impact on the environment during synthesis 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Step A: 3-fluoro-5-formylbenzonitrile: A solution of 3-bromo-5- fluorobenzonitrile (5.00 g, 25.0 mmol) in dry THF (25 mL) was cooled to 0 C and 2M iPrMgCl (15.0 mE, 30.0 mmol) in THF was added dropwise over 5 minutes. The mixture was stirred at 0 C for 15 minutes then at ambient temperature for 1 hour. The mixture was cooled to 0 C and dry DMF (5.81 mL, 75.0 mmol) was added. The mixture was stirred for 17 hours during which time the temperature reached ambient temperature after 2 hours. The mixture was added to ice water (150 mL) and Et20 (100 mL). The biphasic mixture was stirred and treated with 6M HC1 to aqueous pH=3. The organic layer was removed and the aqueous layer extracted with Et20 (2X). The combined Et20 fractions were washed with saturated NaC1 and dried over MgSO4/activated carbon. The dried solution was filtered through a Si02 plug eluting with Et20. The filtrate was concentrated to give the title compound as a yellow solid that was dried in vacuum (3.68 g, 99%). ?H NMR (CDC13) oe 10.0 (s, 1H), 8.00 (s, 111), 7.81-7.86 (m, 111), 7.62-7.67 (m, 111).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BRANDHUBER, Barbara, J.; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; WINSKI, Sharon, L.; WO2014/78323; (2014); A1;,
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