Author: tianli

Reference of 722-92-9, 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.722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, molecular weight is 259.15, as common compound, the synthetic route is as follows.

Intermediate 22: (R)-tert-Butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate (0745) (0746) A 2 L reactor, equipped with a thermometer, was charged with (R)-2-(tert-butoxycarbonyl)-5-(methylsulfonyl)isoindoline-1-carboxylic acid (110 g, 307.08 mmol) under nitrogen. EtOAc (1000 mL) was added and the resulting mixture was stirred for 1 min. The vessel was then charged with 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (84 g, 307.08 mmol), the resulting mixture was cooled to +10¡ã C. and then pyridine (27.3 mL, 337.79 mmol) was added. The reaction was cooled to +5¡ã C., and T3P (50percent in EtOAc, 274 mL, 460.62 mmol) was added at 5¡ã C. over 15 min. The temperature rose to 13.3¡ã C. over the addition, and the resulting solution was allowed to reach room temperature over 20 minutes and left stirring overnight at room temperature. The mixture was cooled to +5¡ã C., and an aqueous solution of citric acid (1N) was added, followed by 500 mL of EtOAc. Stirring was continued for 15 min, then stirring was stopped and the layers separated. The organic layer was washed with aqueous citric acid (1000 mL), and then twice with saturated aqueous NaHCO3 (1000 mL), followed by brine (1000 mL). The organic layer was separated and concentrated under reduced pressure (bath temperature 32¡ã C.). The crude material was dissolved in 550 mL of EtOH at rt, and water (440 mL) was slowly added dropwise over 15 min. Seed crystals (20 mg), were added, and the mixture was left overnight at 20¡ã C. The precipitate was isolated by filtration, washed with a 4:1 mixture of H2O/EtOH (220 mL), and dried under high vacuum. The title compound (132 g, quantitative) was used in the next step without further purification. (0747) LC/MS: m/z=581 [M?H]?, 583 [M+H]+. 1H NMR (400 MHz, DMSO-d6, mixture of rotamers, 1.9*:1) delta 1.34*, 1.46 (s, 9H), 3.20, 3.21*(s, 3H), 4.69-4.88 (m, 2H), 5.60*, 5.62 (s, 1H), 7.6-7.76 (m, 5H), 7.86-7.92 (m, 1H), 7.98, 8.01*(s, 1H), 8.68*, 8.69 (s, 1H), 10.76 (s, 1H). (0748) The seed crystals were obtained from (R)-tert-butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate (0.5 g, 0.86 mmol, prepared as described above for the large scale preparation of intermediate 22). This material was dissolved in ethanol (2.5 ml). Water (2 ml) was added until the point the mixture just became turbid. Spontaneous crystalization occurred after about 30 seconds, and (R)-tert-butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate was obtained after filtration and drying as a colorless solid (0.38 g, 76percent).

The chemical industry reduces the impact on the environment during synthesis 722-92-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14320-38-8, Cyclopent-3-enol, 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, 14320-38-8, blongs to alcohols-buliding-blocks compound. Product Details of 14320-38-8

Step (i): l-[(cyclopent-3-en-l-yloxy)methyl]-4-methoxybenzene To a solution of cyclopent-3-en-l-ol (CAS number 14320-38-8; 15 g, 178 mmol) in dry THF (357 ml) at 0 C under nitrogen was added sodium hydride (60%, 9.27 g, 232 mmol). After fizzing had ceased, to this was then added dropwise l-(chloromethyl)-4- methoxybenzene (CAS number 824-94-2; 31.4 ml, 232 mmol). The reaction was then allowed to warm to room temperature for 17 hours. The reaction mixture was quenched by the addition of methanol and then concentrated in vacuo. The organics were partitioned between ethyl acetate and water. The organics were dried over magnesium sulfate, concentrated in vacuo and purified by column chromatography (silica, 0-50%dichloromethane / petrol) to afford the title compound.1H NMR (400 MHz, OCM-d2) delta ppm 2.33 – 2.47 (m, 2 H), 2.49 – 2.66 (m, 2 H), 3.79 (s, 3 H), 4.20 – 4.32 (m, 1 H), 4.40 (s, 2 H), 5.62 – 5.75 (m, 2 H), 6.86 (d, 7=8.59 Hz, 2 H), 7.24 (d, 7=8.59 Hz, 2 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14320-38-8, its application will become more common.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 111-46-6, 2,2′-Oxybis(ethan-1-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, Recommanded Product: 111-46-6, blongs to alcohols-buliding-blocks compound. Recommanded Product: 111-46-6

The preparation of this compound was adapted from a literature procedure. Into a suspension of tBuOK (5.10 g, 45.5 mmol) in dry THF (125 mL) was added die(thylene)glycol (9.55 g, 90.0 mmol) at 0 C under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 30 min then propargyl bromide (6.69 g, 45.0 mmol) in dry THF (25 mL) was added dropwise. The resulting mixture was allowed to stir at room temperature for 12 h. After completion of the reaction as indicated by NMR, the mixture was diluted with THF and filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (Si02, EtOAc) to give the product as a pale yellow liquid (4.77 g, 93%). NMR (500 MHz, CDC13) delta 4.22 (d, J = 2.4, 2H, CH2C?C), 3.78 – 3.69 (m, 6Eta, CH2), 3.67 – 3.58 (m, 2Eta, CH2OH), 2.45 (t, J = 2.3, 2H, C?CH, OH). 13C NMR (126 MHz, CDC13) delta 79.6 (CH2C?CH), 74.8 (CH2C?CH), 72.6, 70.4, 69.3, 61.9 (CH2OH), 58.6 (CH2C?CH). The spectroscopic data of 39c are in agreement with those previously reported.

The synthetic route of 111-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PERCEC, Virgil; WO2014/190024; (2014); 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. 15852-73-0, name is (3-Bromophenyl)methanol, molecular formula is C7H7BrO, The 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. Computed Properties of C7H7BrO

Step 1 c’: Synthesis of (4′-(Trifluoromethyl)-[1 ,1 ‘-biphenyl]-3-yl)methanol To a solution of 3-bromo benzyl alcohol (0.1 g, 0.53 mM) and 4- (trifluoromethyl)phenyl)boronic acid (0.121 g, 0.64 mM), DMF/water (8:1 ), Na2C03 (0.142 g, 1 .33 mM) and PdCI2(PPh3)2 (0.010 mM) were added. The reaction mixture was heated in a microwave at 1 10 ¡ãC for 6 min. The reaction mixture was quenched with water and extracted with ethyl acetate (3×10 ml). The organic layer was washed with brine, dried over Na2S04 and concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 100-200 mesh, eluted with 15percent ethyl acetate in petroleum ether) to afford the title compound (4’-(trifluoromethyl)-[1 ,1 ‘- biphenyl]-3-yl)methanol as a colorless oil. Yield: 0.108 g( 80percent);1H NMR (DMSO-d6, 300 MHz): delta 7.91 (d, J=8.1 Hz, 2 H), 7.84-7.82 (m, 3 H), 7.70 (m, 1 H), 7.50-7.48 (m, 2H), 5.30 (t, J = 5.7Hz, 1 H, OH), 4.60 (d, J=5.7 Hz, 2 H); MS: m/z 275 (M+Na).

With the rapid development of chemical substances, we look forward to future research findings about 15852-73-0.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; KUMAR, Sanjay; SHARMA, Rajiv; MAHAJAN, Vishal, Ashok; SAWARGAVE, Sangameshwar, Prabhakar; WO2013/128378; (2013); A1;,
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Application of 552331-15-4, 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 552331-15-4, name is 1-(5-Bromo-2-fluorophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Step-2: Synthesis of 1-(5-bromo-2-fluorophenyl)ethan-1-one To a stirred solution of 1-(5-bromo-2-fluorophenyl)ethan-1-ol (5.3 g, 24.195 mmol, 1.0 eq) in THF (50 mL) was added Dess-martin peridionane (12.314 g, 29.034 mmol, 1.2 eq) at 0 C. The resulting mixture was stirred at rt for 15 min. The progress of reaction was monitored by LCMS. The resection mixture was quenched with saturated solution of NaHCO3 (50 mL) extracted with EtOAc (2*50 mL). The combined organic extracts were washed with water (50 mL), with brine (50 mL) dried over Na2SO4 and concentrated under reduced pressure and purified by flash chromatography [silica gel 100-200 mesh; elution 0-5% EtOAc in hexane] to afford the desired compound 1-(5-bromo-2-fluorophenyl)ethan-1-one (3.78 g, 72.00%) as yellow liquid. 1H NMR (400 MHz, CDCl3) delta 7.99 (dd, J=2.63, 6.58 Hz, 1H), 7.61 (ddd, J=2.63, 4.39, 8.77 Hz, 1H), 7.05 (dd, J=8.77, 10.09 Hz, 1H), 2.64 (d, J=4.82 Hz, 3H).

According to the analysis of related databases, 552331-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35364-79-5, 2-(3,4-Dichlorophenyl)ethanol, 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, 35364-79-5, blongs to alcohols-buliding-blocks compound. Quality Control of 2-(3,4-Dichlorophenyl)ethanol

To a solution of alcohol 35 (0.5 mmol) in CH2Cl2 (10 mL) at 0 Cwas added TEA (0.55 mmol, 1.1 equiv) and methanesulfonyl chloride(0.55 mmol, 1.1 equiv). The mixture was stirred at 0 C for anadditional 2 h, and concentrated to provide crude compound 36. To a solution of 2-(3,4-dichlorophenyl)ethan-1-ol (0.5 mmol) andK2CO3 (1 mmol, 2 equiv) in DMF was added compound 36(0.5 mmol). The reaction mixture was stirred at 60 C overnight,cooled, and partitioned between H2O (50 mL) and EtOAc (30 mL).The aqueous layer was extracted twice using EtOAc (30 mL 2).The combined organic layers were washed using brine, dried overNa2SO4, and concentrated. The crude material was purified by flashchromatography to give compound 5 (28%): 1H NMR (400 MHz,CDCl3): d 7.78 (d, J 8.0 Hz, 2H), 7.60 (d, J 8.0 Hz, 2H), 7.53 (d,J 8.0 Hz, 1H), 7.48 (d, J 3.6 Hz, 2H), 7.38 (d, J 3.6 Hz, 1H), 7.20(d, J 8.4 Hz, 1H), 7.01 (d, J 3.6 Hz, 1H), 4.97 (s, 2H), 3.88 (t,J 5.6 Hz, 2H), 3.04 (t, J 5.6 Hz, 2H); 13C NMR (100 MHz, CDCl3):d 149.6, 145.0, 139.3, 133.6, 132.5, 132.2, 130.8, 130.3, 130.2, 129.0,128.8, 128.3, 118.7, 117.8, 112.7, 70.0, 62.7, 35.3; HRMS (ESI): Exactmass calcd for C20H16Cl3N2OS [MH] 437.0049, found 437.0051;HPLC analysis: retention time 5.7 min, peak area 97.6%, 80:20CH3CN/H2O.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,35364-79-5, its application will become more common.

Reference:
Article; Liang, Dongdong; Li, Linhao; Lynch, Caitlin; Mackowiak, Bryan; Hedrich, William D.; Ai, Yong; Yin, Yue; Heyward, Scott; Xia, Menghang; Wang, Hongbing; Xue, Fengtian; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 84 – 99;,
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Adding a certain compound to certain chemical reactions, such as: 4461-39-6, N-(2-Hydroxyethyl)-1,3-propanediamine, 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, Recommanded Product: 4461-39-6, blongs to alcohols-buliding-blocks compound. Recommanded Product: 4461-39-6

General procedure: A suspension oftert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate5(1 eq.), the corresponding amine (2 eq.) and acetic acid (2 – 5 eq.) in DCE (2 ml) was stirred at RT for 30 min.To this suspension was added sodium triacetoxyborohydride (5 eq.).The resulted mixture was stirred at RT for 18 – 72 hrs.The reaction mixture was diluted with 5 ml of saturated sodium carbonate and extracted with DCM (3 x 10 ml).The combined organic layers were dried over sodium sulfate, filtered and concentratedinvacuo.The crude product was purified by Biotage flash chromatography or was used directly in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4461-39-6, N-(2-Hydroxyethyl)-1,3-propanediamine, and friends who are interested can also refer to it.

Reference:
Article; Chen, Yan; Sit, Sing-Yuen; Chen, Jie; Swidorski, Jacob J.; Liu, Zheng; Sin, Ny; Venables, Brian L.; Parker, Dawn D.; Nowicka-Sans, Beata; Lin, Zeyu; Li, Zhufang; Terry, Brian J.; Protack, Tricia; Rahematpura, Sandhya; Hanumegowda, Umesh; Jenkins, Susan; Krystal, Mark; Dicker, Ira D.; Meanwell, Nicholas A.; Regueiro-Ren, Alicia; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1550 – 1557;,
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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. 109-83-1, name is 2-(Methylamino)ethanol. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Methylamino)ethanol

A mixture of 4.50 g (19.17 mmol) of product from 1a, 1.69 g (21.10 mmol) of N-methylaminoethanol (BASF), 6.68 ml (47.90 mmol) of triethylamine and 150 ml dichloromethane is stirred overnight at ambient temperature. The reaction mixture is then washed with 0.5 M HCl, saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution, dried on sodium sulphate and evaporated to dryness in vacuo.C12H19NO4S (273.35)[M+H]+=274TLC: silica gel, dichloromethane/ethanol 19:1, Rf value=0.43

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, 109-83-1, 2-(Methylamino)ethanol.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/197664; (2010); A1;,
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Reference of 2425-41-4, 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. 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol, molecular formula is C12H16O4, The 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.

To a solution of 5109 (1 0.0 g, 44.6 mmol) in dichloromethane (180 ml) under argon were addedbromoacetonitrile (13.0 g, 108.4 mmol), Silver( I) oxide (20.7 g, 89.2 mmol), and tetrabutylammonium iodide (3.3 g, 8.92 mmol), and the resulting mixture was stirred overnight. The mixture was filtered overCelite, and the filtrate was evaporated to give a black residue, which was subjected to flash silica gelcolumn purification on ISCO companion (hexane/ethyl acetate, 15 – 90%) to give 5.55 g (41 %) of thedesired compound S127 as a viscous oil. ESI MS for C15H1sN204 calculated 302.3, observed [M+H]+ 303.3.

According to the analysis of related databases, 2425-41-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLSTICE BIOLOGICS, LTD.; SAKAMURI, Sukumar; BRADSHAW, Curt, W.; ELTEPU, Laxman; MEADE, Bryan, R.; LAM, Son; (237 pag.)WO2018/35380; (2018); A1;,
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Reference of 7397-62-8, 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 7397-62-8 as follows.

Example 36 Butyl 3-amino-6-benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine-2-carboxylate A solution of 1.0 gm (0.008 mol) of butyl glycolate in 8 ml of absolute dioxane was added dropwise to a suspension of 0.4 gm (0.008 mol) of 50% sodium hydride in 5 ml of absolute dioxane, and the mixture was stirred for one hour at room temperature. Then, while the mixture was cooled with ice, a solution of 1.0 gm (0.004 mol) of 1-benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine in 15 ml of absolute dioxane was added, and the mixture was stirred for one hour. The reaction mixture was then poured into about 80 ml of ice-cold water, and the aqueous mixture was extracted three times with ethyl acetate. The combined organic phases were washed twice with water, dried over sodium sulfate and concentrated by evaporation. The residue was purified by column chromatography on silicagel, using toluene/ethyl acetate (7:3) as eluant. Yield: 0.2 gm (14% of theory). Melting point: <20 C. Calc.: molecular peak m/e=342. Found: molecular peak m/e=342. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7397-62-8, its application will become more common. Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4414225; (1983); A;,
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