Tag: M.W=100-200

Electric Literature of 702-82-9 ,Some common heterocyclic compound, 702-82-9, molecular formula is C10H17NO, 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.

3.0 g of compound IV, 3.3 g of 3-amino-1-adamantanol, 2.7 g of potassium carbonate,0.1 g of potassium iodide and 30 mL of tetrahydrofuran were added to a 100 mL reaction flask and mechanically stirred.Reaction at 20 C for 12 hours,Filter, wash the filter cake with 20 mL of tetrahydrofuran, and combine the filtrate.The filtrate was concentrated to dryness at 40 C.Add 30 mL of dichloromethane, stir and dissolve, and the organic phase is passed through 10 mL of water and 10 mL respectively.Wash with brine, separate the layers, and dry the organic phase with 10 g of anhydrous sodium sulfate.filter,The organic phase was concentrated to dryness at 40 C, and then crystallised from 9mL of ethanol and 36mL of isopropyl ether.Filter, dry to constant weight at 40 C,4.4 g of compound V were obtained with a yield of 93.4%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,702-82-9, its application will become more common.

Reference:
Patent; Zhuhai Federation Pharmaceutical Co., Ltd.; Yin Bangzhi; Mao Jiaohuang; Xu Huafeng; Qiao Mingfu; Liang Qingyong; (12 pag.)CN109776372; (2019); A;,
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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. 27646-80-6, name is 2-Methyl-2-(methylamino)propan-1-ol. A new synthetic method of this compound is introduced below., SDS of cas: 27646-80-6

To a mixture of 2,2-difluoroethyl trifluoromethanesulfonate ( 1.0 g, 4.67 mmol), 2- methyl-2-(methylamino)propan-l-o3 (0.48 g, 4.67 mmol) in THF (10 mL) was added DIPEA (0.65 g, 4.8 mmol). The resulted mixture was stirred at 70 °C for 18 h, then concentrated to dryness. The residue was stirred in EtOAc (40 mL) for 5 min, then filtered. The filtration was concentrated in vacuo. The crude residue was purified via silica chromatography and a gradient of 10percent- 100percent EtOAc in hexanes to afford 2- ((2,2~difluoroethyl)(methyi)aniino)-2-methyipropan-l-ol as a colorless oil (0.66 g).

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, 27646-80-6, 2-Methyl-2-(methylamino)propan-1-ol.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy, Duncan; BRAMELD, Kenneth, Albert; GOLDSTEIN, David, Michael; (230 pag.)WO2018/136401; (2018); A1;,
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Reference of 767-90-8, 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 767-90-8, name is (2-Ethylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (2-ethylphenyl)metha- nol (13-1, 1.00 g, 7.3 mmol) in DMF (25 mE) at room temperature under nitrogen, N135 (2.6 g, 14.6 mmol) and triphenylphosphine (4.03 g, 15.3 mmol) were added sequentially. The mixture was heated to 50 C. overnight, cooled to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted twice more with dichioromethane and the organic layers were combined, washed with brine, dried, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with 10% ethyl acetate in hexanes to give 1-(bromomethyl)-2-ethylbenzene (13-2, 1.1 g) as an oil.

According to the analysis of related databases, 767-90-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Market, Robert V.; Savage, Michael M.; Young, Brandon M.; (49 pag.)US2018/312498; (2018); A1;,
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Synthetic Route of 39590-81-3, 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. 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane. A new synthetic method of this compound is introduced below.

Method A, Step 1To a solution of i-hydroxymethylcyclopropylmethanol AA1 (10 g, 98 mmol) in DMF (300 ml_) was added tert-butylchlorodiphenylsilane (26.3 ml_, 100 mmol) followed by diisopropylethylarnine (170 mL) and the reaction was stirred at RT overnight. The final mixture was quenched with water and extracted with EtOAc. The organic layer was washed with 3N HCI, sat NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography over silica gel (eluted with DCM/MeOH 100:0 to 80:20) to give 18.5 g (55%) of product AA2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2009/61699; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride, 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, Formula: C5H12ClNO, blongs to alcohols-buliding-blocks compound. Formula: C5H12ClNO

A mixture of 5,6-dimethyl-4-(4-(1-methyl-1H-pyrazol-3-yl)benzyl)picolinic acid (30.0 mg), (1S,2S)-2-aminocyclopentanol hydrochloride (19.3 mg), WSC (26.8 mg), HOBt (18.9 mg) and triethylamine (28.3 mg) in DMF (1 mL) was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and extracted twice with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), and solidified with ethyl acetate-hexane to give the title compound (30.0 mg). 1H NMR (300 MHz, CDCl3) delta1.60-1.96 (4H, m), 2.03-2.18 (1H, m), 2.22 (3H, s), 2.24-2.34 (1H, m), 2.53 (3H, s), 3.94 (3H, s), 3.95-4.03 (1H, m), 4.05 (2H, s), 4.08-4.18 (1H, m), 4.71 (1H, brs), 6.49 (1H, d, J = 1.7 Hz), 7.11 (2H, d, J = 8.0 Hz), 7.36 (1H, d, J = 1.9 Hz), 7.69 (2H, d, J = 8.0 Hz), 7.88 (1H, s), 8.20 (1H, brs).

The synthetic route of 68327-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7589-27-7, 2-(4-Fluorophenyl)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, 7589-27-7, blongs to alcohols-buliding-blocks compound. Computed Properties of C8H9FO

To a 40 mL vial equipped with a stir bar was added 4-bromo-2,6-difluorophenol (1.04 g, 5.00 mmol), 2-(4-fluorophenyl)ethanol (700 mg, 5.00 mmol), triphenylphosphine (1.57 g, 6.00 mmol) and THF (25 mL). To the stirred solution was added DIAD (1.17 mL, 6.00 mmol). The solution warmed to a mild reflux, then cooled within 5 minutes. The solution was stirred at r.t. for 18h. The reaction solution was concentrated in vacuo. The resulting residue was dissolved in a mm. of acetone, then was concentrated onto Celite in vacuo. The resulting powder was subjected to Si02 purifciation (80g column, hexanes : EtOAc 100: 0- 80:20) to afford 5-bromo- 1,3 -difluoro-2-(4-fluorophenethoxy)benzene (1.552 g, 94percent). ?HNMR(500MF-Tz, CDC13) 7.26 – 7.21 (m,2H), 7.11 – 7.04 (m, 2H), 7.03 – 6.97 (m, 2H), 4.30 (t, J=6.9 Hz, 2H), 3.06 (t, J=6.9 Hz,2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7589-27-7, its application will become more common.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
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Application of 37729-18-3, 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. 37729-18-3, name is 2-([1,1′-Biphenyl]-4-yl)ethanol. A new synthetic method of this compound is introduced below.

Compound 30:Acrylic acid (13.5 mg, 0.05 mmol) was added sequentially to a 25 mL two-necked flask,2-biphenylethyl alcohol (49.5 mg, 0.25 mmol),N, O-bis (diethylsilyl) trifluoroacetamide (213.6 mg, 0.75 mmol)Potassium peroxy monosulfonate (307.0 mg, 0.50 mmol)The gas was replaced with dry N2 for 3 times,Finally, dry tetrahydrothiopyran (0.5 mL) was added under N2.Stirred at room temperature and heated to 50 C to carry out the reaction,Until the thin layer chromatography monitoring of raw materials is completed.At the end of the reaction, 15.0 mL of NaCl solution was added at room temperature,Extracted with ether 15.0 mL three times,The combined organic phase was distilled under reduced pressure and the product was purified by column chromatography in 65% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,37729-18-3, 2-([1,1′-Biphenyl]-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Normal University; Han Wei; Zhao Hongyuan; (19 pag.)CN107056732; (2017); A;,
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Related Products of 14002-80-3, 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. 14002-80-3, name is Methyl 3-hydroxy-2,2-dimethylpropanoate, molecular formula is C6H12O3, 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.

Step (i): Methyl 3-(2-methoxyethoxy)-2,2-dimethylpropanoate (39) Sodium hydride (60 % wt in oil) (3.14 g, 78 mmol) was added to a stirred solution of methyl 3- hydroxy-2,2-dimethylpropanoate (5 mL, 39.2 mmol) in DMF (5.6 mL) at 0C, after 5 min 1- bromo-2-methoxyethane (7.4 mL, 78 mmol) was added dropwise, and the reaction mixture was allowed to stir for 3h. The reaction was quenched with sat. NH4CI (aq.) (30 mL) and the aqueous layer was extracted with DCM (2 x 50 mL), the combined organic layers were dried (MgS04), filtered and concentrated in vacuo. The crude oil was dissolved in EtOAc (125 mL) and washed with water (3 x 40 mL), dried (MgS04), filtered and concentrated in vacuo. The material was purified by vacuum distillation (68-69C, 4.4 mbar) to afford methyl 3-(2- methoxyethoxy)-2,2-dimethylpropanoate (39) (1.83 g, 25 %) as a colourless oil: 1 H NMR (400 MHz, CDCIs) delta: 3.68 (s, 3H), 3.60-3.58 (m, 2H), 3.52-3.50 (m, 2H), 3.49 (s, 2H), 3.37 (s, 3H), 1.19 (s, 6H).

According to the analysis of related databases, 14002-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF LEICESTER; ANDREW, Peter William; LONNEN, Rana; DAMASO, Mafalda Pires; FRICKEL, Fritz-Frieder; HIRST, Simon Christopher; DAVIES, Mark William; HAMZA, Daniel; WO2013/83975; (2013); A2;,
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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 66102-69-0, name is 3-Amino-2-benzylpropan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C10H15NO

Preparation of 3-amino-2-benzyl-1-propanesulfonic acid (Compound N4); To a cold (-78 C.) solution of 3-hydroxypropionitrile (1 g, 14.06 mmol) in THF (30 mL), was added a solution of lithium bis(trimethylsilyl)amide (1 M in THF, 28 mL). After the reaction mixture was stirred for 1 h at -78 C., benzyl bromide (1.67 mL, 14.06 mmol) was added dropwise and the reaction mixture was warmed to reach 0 C. at which temperature the mixture was stirred overnight. The reaction was quenched with 1N HCl and extracted with EtOAc. The organic layer was washed with 1N HCl, dried over Na2SO4 and concentrated. The residue was applied on silica gel column (eluant:Hexanes:EtOAc 70:30 to 50:50) to afford 1.3 g (69%) of the 2-benzyl-3-hydroxypropionitrile. 1H NMR (300 MHz, CDCl3) delta 2.80 (bs, 1H), 2.95 (m, 3H), 3.77 (m, 2H), 7.20-7.35 (m, 5H); 13C NMR (125 MHz, CDCl3) delta 34.71, 37.03, 61.98, 120.78, 127.58, 129.06, 129.25, 136.71. The dialkylated product was isolated in 8.5% yield. To a solution of 2-benzyl-3-hydroxypropionitrile (obtained in step 1, 3 g, 24.75 mmol) in EtOH (60 mL) was added an aqueous solution of NH4OH (30%, 20 mL), followed by Ra-Ni (3 g). The suspension was stirred under atmosphere H2 pressure for 15 hours and then filtered. The filtrate was concentrated under high vacuum; and the residual product (3-1mino-2-benzyl-1-propanol) was used in the next step without purification. A solution of the crude 3-amino-2-benzyl-1-propanol (4.5 g, 27.23 mmol) in anhydrous CHCl3 (24 mL) was saturated with HCl (g), and then SOCl2 (5.2 mL, 71.0 mmol) was added dropwise at reflux. The reaction was maintained under reflux for an additional 2 hours. The reaction was then concentrated to yield a syrupy product. The crude 3-chloro-2-benzyl-1-propylamine thus obtained was used in the next step without further purification. A solution of the crude 3-chloro-2-benzyl-1-propylamine (obtained in step 3) in water (10 mL) was added dropwise to a solution of Na2SO3 (6.8 g, 54.46 mmol) in water (25 mL) under reflux. After the end of the addition, the reaction was stirred at reflux for 1 hour, then cooled down and concentrated under reduced pressure. HCl (conc. 16 mL) were added to dissolve the aminosulfonic acid and precipitate the inorganic salts which were removed by filtration. The filtrate was concentrated; and ethanol was added. The title amino sulfonic acid was precipitated as white solid which was collected by filtration, washed with EtOH and Et2O, then dried under high vacuum to give a white solid (1.87 g, 30% yield over three steps). 1H NMR (500 MHz, D2O) delta 2.52 (m, 1H), 2.8 (m, 2H), 2.94 (m, 2H), 3.08 & 3.18 (ABX, J=13.0 & 7.0 Hz, 2H), 7.25-7.37 (m, 5H). 13C NMR (125 MHz, D2O) delta 35.47, 37.78, 42.67, 52.55, 127.15, 129.09, 129.54, 138.32. ES-MS 228 (M-1).

With the rapid development of chemical substances, we look forward to future research findings about 66102-69-0.

Reference:
Patent; Neurochem (International) Limited; US2006/223855; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3597-91-9, [1,1′-Biphenyl]-4-ylmethanol, 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: 3597-91-9, blongs to alcohols-buliding-blocks compound. Recommanded Product: 3597-91-9

General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57%) as a pale yellow solid. Yields of 57% of 2a and 38% of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3597-91-9, [1,1′-Biphenyl]-4-ylmethanol, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Xingguo; Ma, Shengming; Synthesis; vol. 50; 8; (2018); p. 1629 – 1639;,
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