Tag: M.W=100-200

Synthetic Route of 7218-43-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 7218-43-1, name is 2-[2-(2-Propynyloxy)ethoxy]ethanol. This compound has unique chemical properties. The synthetic route is as follows.

(Wurz, R. P.; et al., “Click Chemistry Platform” for the Rapid Synthesis of Bispecific Molecules for Inducing Protein Degradation. Journal of medicinal chemistry 2018, 61, 453-461). The method, as described by Oberborsch was used to prepare this compound (WO2009124746 Al). To a solution of the alcohol SR3-062 (3.00 g, 20.81 mmol) and n-Bu4NCl (1.908 g, 6.867 mmol) in DCM (102 mL) at 0 C were added NaOH (102 mL, aq. 35%) and ieri-butyl bromoacetate (9.225 mL, 62.427 mmol). The mixture was stirred at room temperature for 5 h and diluted with DCM (25 mL) and water (25 mL). The layers were separated and the organic layer washed with water (2 x 20 mL), brine (1 x 20 mL), dried (Na2S04), and evaporated in vacuo. Purification by flash column chromatography using EtOAc:hexane (5-50%) as eluent afforded SR3-066 (Wurz, R. P.; et al., “Click Chemistry Platform” for the Rapid Synthesis of Bispecific Molecules for Inducing Protein Degradation. Journal of medicinal chemistry 2018, 61, 453-461) as a pale- yellow oil (4.724 g, 87%). NMR (500 MHz, Chlorol’orn /) d 4.23 (d, J = 2.4 Hz, 2H), 4.05 (s, 2H), 3.79-3.65 (m, 8H), 2.45 (t, J = 2.4 Hz, 1H), 1.50 (s, 9H). 13C NMR (126 MHz, CDCh) d 169.7, 81.5, 79.7, 74.5, 70.7, 70.6, 70.4, 69.1, 69.1, 58.4, 28.1. HRMS (ESI+): m/z calcd for C13H23O5 (M+H)+ 259.1540, found 259.1547, m/z calcd for Ci3H2205Na (M+Na)+ 281.1359, found 281.1365. HPLC-MS (ESI+): m/z 281.2 [100%, (M+Na)+]

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 7218-43-1, 2-[2-(2-Propynyloxy)ethoxy]ethanol.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Nicholas J.; LAWRENCE, Harshani; (0 pag.)WO2020/14489; (2020); A2;,
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Reference of 626-18-6 ,Some common heterocyclic compound, 626-18-6, molecular formula is C8H10O2, 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.

1,3-benzene dimethanol (82.5 mg, 0.5971 mmol), compound 14 (191.2 mg, 0.5971 mmol), in dichloromethane (5 mL) solution, EDCl / HCl (228.9 mg, 1.1942 mmol) and DMAP (14.6 mg 0.1194 mmol)) were added , under an argon atmosphere and stirred at room temperature for 1 hour. The solvent was evaporated, and the residue was purified by column chromatography (hexane: ethyl acetate = 4: 1 to 2: 1) to give the title compound 17-1 (112.7 mg, 0.2558 mmol, 42.84%, colorless oil) was Obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,626-18-6, its application will become more common.

Reference:
Patent; THE UNIVERSITY OF TOKYO; TOHOKU UNIVERSITY; OHWADA, TOMOHIKO; NAKAMURA, SHO; JUNG, SEJIN; OTANI, YUKO; SAYAMA, MISA; AOKI, JUNKEN; (80 pag.)JP2016/17036; (2016); A;,
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Related Products of 111-46-6 ,Some common heterocyclic compound, 111-46-6, molecular formula is C4H10O3, 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.

Synthesis of 2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate (Compound A3)Into a 2000-mL 3 -necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 2-(2 -hydroxy ethoxy)ethan-l-ol (A2, 42.4 g, 399.55 mmol, 1.00 equiv) in dichloromethane (1000 mL) and triethylamine (27.9 g, 275.72 mmol, 0.25 equiv). To the above was added p-toluenesulfonyl chloride (19.1 g, 100.18 mmol, 0.50 equiv). After stirring for 1 h at 25C, the resulting mixture was washed with 1×500 mL of aq. potassium hydrosulfate (1M) and 1×500 mL of aq. sodium bicarbonate (5%) respectively. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (100: 1). This resulted in Compound A3 as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111-46-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COLLETTI, Steven, L.; TUCKER, Thomas, J.; TELLERS, David, M.; KIM, Boyoung; BURKE, Rob; CALATI, Kathleen, B.; STANTON, Matthew, G.; PARMAR, Rubina, G.; AARONSON, Jeffrey, G.; WANG, Weimin; WO2015/69587; (2015); A2;,
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Reference of 116-02-9, Adding some certain compound to certain chemical reactions, such as: 116-02-9, name is 3,3,5-Trimethylcyclohexanol,molecular formula is C9H18O, 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 116-02-9.

a) 426g (3,00 Mol) of Homomenthol is added to the above-mentioned filtrate, the temperature is raised to 60C and under stirring and a vacuum of 100mbar the Ethyl acetate is distilled off the reaction mixture. Then 56g of Sulfuric acid are added at a temperature of 50C within 20minutes, stirring is continued for 6h. For work-up 500g of Toluene are added to the reaction mixture and after cooling to 5-10C the dosage of 500g of iced water follows. After separation of the water layer the organic layer is washed to neutral with aqueous Sodium hydroxide solution (10% w/w) and finally with saturated aqueous Sodium chloride solution. After separation of the water layer the organic layer is distilled resulting 250g (0,93 Mol) of product. Yield (overall): 58% of theory.

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. 116-02-9, 3,3,5-Trimethylcyclohexanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Symrise AG; Stuhlmann, Dominik; Meyer, Imke; Koch, Oskar; Oertling, Heiko; Herrmann, Martina; Goemann, Claudia; EP2810934; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.75853-18-8, name is 2,3-Difluorobenzyl alcohol, molecular formula is C7H6F2O, molecular weight is 144.12, as common compound, the synthetic route is as follows.SDS of cas: 75853-18-8

tert-Butyl-(2,3-difluoro-benzyloxy)-dimethyl-silane To a solution of (2,3-difluoro-phenyl)-methanol (5.0 g, 35 mmol), imidazole (4.9 g, 72 mmol) and DMF (40 mL) was added tert-butyldimethylchlorosilane (5.4 g, 36 mmol). After stirring at ambient temperature for 24 hours, the mixture was partitioned between 400 mL of ether and 100 mL of water. The organic layer was washed twice with water, dried over MgSO4, filtered and concentrated in vacuo, affording 6.8 g of tert-butyl-(2,3-difluoro-benzyloxy)-dimethyl-silane as a colorless oil. 1H NMR (400 MHz, CDCl3) delta7.22 (m, 1H), 7.04 (m, 2H), 4.79 (s, 2H), 0.91 (s, 9H), 0.12 (s, 6H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75853-18-8, 2,3-Difluorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US6235764; (2001); B1;,
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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. 4084-38-2, name is 2,3,5,6-Tetrafluorobenzyl alcohol. A new synthetic method of this compound is introduced below., Formula: C7H4F4O

Under a nitrogen atmosphere, 182 mg of l-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride was added to a mixture of 128 mg of 2, 3, 5, 6-tetrafluorobenzyl alcohol, 128 mg of (IR) -cis-3-cyano-2, 2- dimethylcyclopropanecarboxylic acid, 5 mg of 4- dimethylaminopyridine and 5 mL of chloroform, followed by stirring the mixture at room temperature for 18 hours. The reaction mixture was added to water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To a solution of the residue dissolved in 5 mL of anhydrous tetrahydrofuran were added 0.06 mL of triethylamine, 0.04 mL of acetic anhydride and 5 mg of 4- dimethylaminopyridine, followed by stirring the mixture at room temperature for 18 hours to acetylate the remaining benzyl alcohol. To the reaction mixture was added an aqueous saturated sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The resultant residue was subjected to silica gel chromatography to obtain 34 mg of 2,3,5,6- tetrafluorobenzyl (IR) -cis-3-cyano-2, 2-dimethylcyclopropane carboxylate represented by the following formula:(hereinafter referred to as the present compound (I)) as a colorless liquid. 1H-NMR (CDCl3, TMS) delta (ppm) : 1.28 (s, 3H), 1.46 (s,3H), 1.77 (d, IH, J = 8.2 Hz), 1.96 (d, IH, J = 8.2 Hz ), 5.29 (d, IH, J = 12.3 Hz ), 5.34 (d, IH, J = 12.3 Hz ), 7.10-7.14 (m, IH)

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, 4084-38-2, 2,3,5,6-Tetrafluorobenzyl alcohol.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/64025; (2009); A1;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 10602-04-7, name is (4-Ethynylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. name: (4-Ethynylphenyl)methanol

To a solution of (4-ethynylphenyl)methanol 1 (0.52 g, 4 mmol) in DCM (20 mL) was added PBr3 (1.08 g, 4 mmol) at 0 °C under N2, the reaction mixture was stirred at room temperature for 1 hour. After consumption of the starting material (by TLC), diluted with water and extracted with DCM. Combined organic extracts were dried over anhydrous MgSO4 and concentrated under reduced pressure to obtain crude product, which was purified by silica gel column chromatography(EtOAc/Hexane 1: 6) to afford compound 2 (0.3 g, 68percent) as yellow oil. ?H NMR (300 MHz, CDC13) 7.56 (d, J= 8.4 Hz, 2H), 7.37 (d, J= 8.2 Hz, 2H), 4.49 (s, 2H), 4.47 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 10602-04-7.

Reference:
Patent; ABBVIE INC.; MICHAELIDES, Michael; HANSEN, Todd; DAI, Yujia; ZHU, Guidong; FREY, Robin; GONG, Jane; PENNING, Thomas; CURTIN, Michael; MCCLELLAN, William; CLARK, Richard; TORRENT, Maricel; MASTRACCHIO, Anthony; KESICKI, Edward A.; KLUGE, Arthur F.; PATANE, Michael A.; VAN DRIE, John H. Jr.; JI, Zhiqin; LAI, Chunqiu C.; WANG, Ce; (1190 pag.)WO2016/44770; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 431-38-9, 3-Amino-1,1,1-trifluoropropan-2-ol, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

[1369] A solution of 3-amino-1,1,1-trifluoropropan-2-ol (0.016 g, 0.122 mmol), HATU (0.046 mg, 0.122 mmol), and 3-amino-6-(5-(3-amino-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl)-2-methylphenyl)pyrazine-2-carboxylic acid (0.030 g, 0.081 mmol) (single enantiomer, synthesized according to procedure in Example 38) in DMF (0.810 mL) was stirred at rt for 5 min, treated with triethylamine (0.034 mL, 0.243 mmol), and stirred at rt for 30 min. The reaction mixture was concentrated and purified by flash column chromatography using methanol in dichloromethane (0% to 20%) to give the desired product that still contained some impurities. This material was repurified by flash column chromatography using ethyl acetate in hexanes (0% to 100%) to give the desired product as a mixture of diastereomers. The mixture of diastereomers was separated via preparative chiral HPLC (Chiral Technologies ChiralPak IA [20250 mm, 5 micron], eluting with 15% ethanol in hexanes, at flow rate of 20 mL/min, loading about 8 mg in 1.8 mL ethanol) to give the first eluting diastereomer (3.20 mg, 8.21%) as 43A and the second eluting diastereomer (3.00 mg, 7.69%) as 43B. The first diastereomer that eluted had a retention time of 12.2 min. The second diastereomer that eluted had a retention time of 16.6 min. 43A: LCMS for C18H18F6N5O4(M+H)+: m/z=482.1; Found: 482.1. 43B: LCMS for C18H18F6N5O4 (M+H)+: m/z=482.1; Found: 482.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,431-38-9, 3-Amino-1,1,1-trifluoropropan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Douty, Brent; Ai, Yanran; Burns, David M.; Combs, Andrew P.; Falahatpisheh, Nikoo; Levy, Daniel; Polam, Padmaja; Shao, Lixin; Shepard, Stacey; Shvartsbart, Artem; Yue, Eddy W.; (132 pag.)US2020/2295; (2020); A1;,
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Related Products of 112-27-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 112-27-6, name is 2,2′-(Ethane-1,2-diylbis(oxy))diethanol. This compound has unique chemical properties. The synthetic route is as follows.

Add 1 mmol of triethylene glycol to the three-necked flask,Add 1 mmol of pyridine,Dissolve with 20 ml of dichloromethane.Stir in a 0 oC ice bath.Dissolve 1 mmol of p-methylbenzenesulfonyl chloride with dichloromethane.Slowly drip into three-necked flask.The reaction was washed with hydrochloric acid after 3 h,The organic layer was washed with water until the aqueous solution was neutral.Drying with anhydrous sodium sulfate,Column chromatography yielded the product.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 112-27-6, 2,2′-(Ethane-1,2-diylbis(oxy))diethanol.

Reference:
Patent; Gannan Normal University; Wu Yongquan; Zeng Guanjie; Wu Renmiao; Fan Xiaolin; (15 pag.)CN105061515; (2017); B;,
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Reference of 27489-62-9, 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. 27489-62-9, name is trans-4-Aminocyclohexanol. A new synthetic method of this compound is introduced below.

To a solution of trans-A- aminocyclohexanol (3 g, 26 mmol) in DMF (130 mL) at 0 C was added 60% sodium hydride in oil. The reaction mixture was stirred at 0 C for lh and then 4-fluorobenzonitrile (3.9 g, 32.6 mmol) was added. It was heated to 60 C for 2h and stirred for 12 h at room temperature. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried, filtered, and concentrated under reduced pressure to provide the titled compound (2.5 g, 44% yield). NMR (300 MHz, DMSO-c¾): 67.72 (d, J = 9 Hz, 2H), 7.09 (d, J = 9 Hz, 2H), 4.48-4.34 (m, 1H), 2.68-2.55 (m, 1H), 2.07-1.94 (m, 2H), 1.85-1.71 (m, 2H), 1.46-1.11 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27489-62-9, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; HAMMOCK, Bruce, D.; HWANG, Sung, Hee; WECKSLER, Aaron, T.; MORISSEAU, Christophe; WO2012/112570; (2012); A1;,
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