Month: January 2021

Application of 23147-58-2 ,Some common heterocyclic compound, 23147-58-2, molecular formula is C4H8O4, 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.

Example 68 (S)-N-((S)-5-((l-(2-Cyanophenyl)-lH-indazol-3-yl)methyl)-4-oxo-2,3,4,5- tetrahydrobenzo [b] [ 1 ,4]oxazepin-3 -yl)-2-(2 -hydroxyethylamino)propan amide Na(OAc)3BH (14.2 mg, 67.0 muetaiotaomicron, Eq: 1.4) was added to a solution of (S)-2-amino-N- ((S)-5-((l-(2-cyanophenyl)-lH-indazol-3-yl)methyl)-4-oxo-2,3,4,5- tetrahydrobenzo[b][l ,4]oxazepin-3-yl)propanamide (23 mg, 47.9 muetaiotaomicron, Eq: 1.00) and glycolaldehyde dimer (3.16 mg, 26.3 muetaiotaomicron, Eq: 0.55) in DCM (1.5 mL). After 72 h. at RT, the mixture was diluted with NaHC03 and extracted with DCMThecombined extracts were concentrated. The residue was purified by preparative TLC to give the title compound (16 mg, 95 %) as a solid. MS m/z 525 (MH+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23147-58-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DONNELL, Andrew F.; HAN, Xiaochun; KESTER, Robert Francis; KONG, Norman; LE, Kang; LOU, Yan; MICHOUD, Christophe; MOLITERNI, John Anthony; REMISZEWSKI, Stacy; RUPERT, Kenneth Carey; YUN, Weiya; WO2014/23708; (2014); A1;,
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Electric Literature of 756520-66-8, 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 756520-66-8, name is 1-(2,6-Dichloro-3-fluorophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

1-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol 37 (24.00 g, 114.81 mmol) was dissolved in 300 mL of CH2ClCH2Cl. The solution was cooled to -5 C. To the solution was successively added Boc-L-proline (16.06 g, 74.63 mmol), EDCI (17.61 g, 91.85 mmol) and DMAP (1.68 g, 13.78 mmol). The resulting mixture was continued to stir overnight and diluted with 100 mL of water. The organic layer was collected, washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography (PE/EA 100:1-50:1, v/v) to afford (1S)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol. (7.00 g, 58% yield). 1H NMR (400 MHz, CDCl3) delta 7.26 (dd, J = 4.8, 8.8 Hz, 1H), 7.02 (dd, J = 8.0, 8.8 Hz, 1H), 5.57 (q, J = 6.8 Hz, 1H), 2.86 (s, 1H), 1.64 (d, J = 6.8 Hz, 3H).

According to the analysis of related databases, 756520-66-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Dengyou; Zhang, Xiaowei; Ai, Jing; Zhai, Yun; Liang, Zhongjie; Wang, Ying; Chen, Yi; Li, Chunpu; Zhao, Fei; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6804 – 6820;,
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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. 5339-85-5, name is 2-(2-Aminophenyl)ethanol. A new synthetic method of this compound is introduced below., HPLC of Formula: C8H11NO

K2CO3 (0.0109 mol) and 4-(2-chloro-ethyl)-morpholine (1 HC1) (0.0036 mol) were added to a solution of 2-ethanol-aniline (0.0036 mol) in CH3CN (15 ml). The reaction was stirred at 80C for 24 hours and then cooled down to room temperature. The precipitate was filtered off and rinsed with CH3CN. The solution was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (eluent: CH2CI2/CH30H/NH40H 98/2/0. 1 ; 35-70 urn). The pure fractions were collected and the solvent was evaporated, yelding 0.7g of 2-[2-(2-morpholin-4-yl-ethylamino)-phenyl]-ethanol (77%)

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, 5339-85-5, 2-(2-Aminophenyl)ethanol.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58869; (2005); A1;,
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Related Products of 767-90-8, Adding some certain compound to certain chemical reactions, such as: 767-90-8, name is (2-Ethylphenyl)methanol,molecular formula is C9H12O, 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 767-90-8.

To a cooled (0C) solution of compound 29 (55.0 g, 404 mmol) in CH2C12 (400 mL) was added Dess-Martin periodinane (177 g, 417 mmol) portionwise. After stirring for lh at r.t., the reaction mixture was quenched with saturated aqueous Na2S2O3 (300 mL) and saturatedaqueous NaHCO3 (500 mL). The mixture was extracted with CH2C12 (3x 300 mL). The combined organic extracts were washed with water and brine, dried over Na2SO4 and concentrated to yield 51.0 g of crude compound 30 as a yellow solid.

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. 767-90-8, (2-Ethylphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AICURIS GMBH & CO. KG; DONALD, Alastair; URBAN, Andreas; BONSMANN, Susanne; WEGERT, Anita; GREMMEN, Christiaan; SPRINGER, Jasper; (376 pag.)WO2019/86141; (2019); A1;,
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Synthetic Route of 110-73-6, 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 110-73-6 as follows.

2-Bromothiophene (1.19 mL, 12.3 mmol, CAS 1003-09-4), copper(I) iodide (350 mg, 15 mol %), copper powder (117 mg, 15 mol %, CAS 7440-50-8) and potassium phosphate tribasic (5.22 g, 24.6 mmol) were suspended in 2-(ethylamino)ethanol (12 mL) and heated at 80 C. for 20 h under Ar. After this time, the reaction mixture was allowed to cool to room temperature and water (40 mL) added. The solution was extracted with diethyl ether (3¡Á40 mL), and the combined organic fractions washed with brine (1¡Á60 mL), dried over MgSO4 and the solvent removed in vacuo. Purification was undertaken by silica gel column chromatography (column loaded using 3% Et3N/hexane) using 2:1 hexane/ethyl acetate to elute the product as an orange oil (1.02 g, 5.96 mmol, 48%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,110-73-6, its application will become more common.

Reference:
Patent; University of Notre Dame du Lac; Smith, Bradley; US2015/5501; (2015); A1;,
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Synthetic Route of 7250-55-7, 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. 7250-55-7, name is Dimethyl 3-hydroxypentanedioate, molecular formula is C7H12O5, 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 dimethyl 3-hydroxypentanedioate (20 g, 114 mmol) in CH2CI2 (100 mL) was added lH-imidazole (15.46 g, 227 mmol) and TBDPSC1 (46.8 g, 170 mmol) at 25C. The solution was stirred at 25C for 3 h, and the mixture was filtrated and the filter cake was washed by CH2CI2 (100 mL). The filtrate was concentrated in vacuo to afford the crude product, which was purified by gradient elution on S1O2 (ISCO, 120 g RediSep Gold column, 0 to 10% EtO Ac/Pet. ether over 90 min, dry-loaded) to afford the title compound. LRMS (M+H)+: 437.2.

According to the analysis of related databases, 7250-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; EMBREY, Mark, W.; HARTINGH, Timothy John; LABROLI, Marc; RAHEEM, Izzat, T.; (75 pag.)WO2019/160783; (2019); 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. 395-23-3, name is Phenyl(4-(trifluoromethyl)phenyl)methanol. A new synthetic method of this compound is introduced below., Application In Synthesis of Phenyl(4-(trifluoromethyl)phenyl)methanol

General procedure: A solution of 1,1-diarylmethanol, 1r-w (200mg, 0.80-1.08mmol) in dry CH2Cl2 (5mL) and TMSN3 (1.5equiv) were placed in a 25mL round-bottom flask fitted with guard tube. InBr3 (2mol%) was added to this reaction mixture. The contents were stirred at room temperature and the progress of reaction was monitored by TLC analyses. After stirring the contents for appropriate time period, the reaction was quenched with water. The product was extracted with CH2Cl2 (3¡Á15mL), washed with 10% Na2CO3 (20mL), water (20mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to give brownish oil. Purification by flash chromatography afforded the products 2r-w.

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, 395-23-3, Phenyl(4-(trifluoromethyl)phenyl)methanol.

Reference:
Article; Kumar, Anil; Sharma, Ramesh K.; Singh, Tej V.; Venugopalan, Paloth; Tetrahedron; vol. 69; 50; (2013); p. 10724 – 10732;,
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Application of 50910-54-8 , The common heterocyclic compound, 50910-54-8, name is trans-4-Aminocyclohexanol hydrochloride, molecular formula is C6H14ClNO, 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.

EXAMPLE 51 iV-(4-^ralpha?5-HvdroxycvclohexyI)-./V-methyl-f24i31-benzoxadiazole-5-carboxaniiderra?5-4-aminocyclohexanol hydrochloride (60.6 g, 0.40 mol) and NaHCO3 (14Og) were dissolved in water (700 ml). Ethyl acetate (500 ml) was added and the mixture stirred rapidly using a mechanical stirrer whilst a solution of ethyl chloroformate (48 ml) in ethyl acetate (200 ml) was added slowly. The mixture was stirred overnight and then ethyl acetate (1 1) and water (500 ml) were added to dissolve the precipitate. The aqueous was extracted with ethyl acetate (2×500 ml) and the combined organic phases were washed with 2N HCl, dried over Na2SO4, and the solvent evaporated, to give a white solid (73.7g). This material was dissolved in dry THF (600 ml) and the solution slowly (~ Ih) added to a suspension OfLiAlH4 (29.6g) in THF (600 ml). After stirring overnight at 20C the mixture was cooled in an ice bath and a solution of sodium hydroxide (77g) in water (50 ml) was slowly added. After Ih, some celite was added and the mixture was filtered and washed with dichloromethane. The filtrate was dried (MgSO4) and evaporated under vacuum to give tra?s-4-methylaminocyclohexanol a white solid (45.9g). ;r¡ã?s-4-Methylaminocyclohexanol (37.1g, 0.28 mol), [2,l,3]-benzoxadiazole-5-carboxylic acid (42.7g, 0.26 mol), DMAP (32g, 0.26 mol), HOBT (1 Ig, 0.08 mol) and triethylamine (54 ml) were dissolved in dichloromethane (750 ml) and after 15 minutes, EDCI (10Og, 0.52 mol) was added and the mixture refluxed for 2h. The mixture was washed with 2N HCl (500 ml) and NaHCO3 solution (500 ml), dried over MgSO4 and then concentrated under vacuum. The residue was chromato graphed on silica gel using ethyl acetate/chloroform (3:1) as eluant to give the title product as a white solid (37g) after trituration with ethyl acetate. Mp = 170- 171C, LC-MS, MH+ = 276; 1H NMR (300 MHz, CDCl3, rotamers) delta 7.92 (d, J = 9.0 Hz, IH); 7.82 (s, IH); 7.40 (d, J = 9.0 Hz, IH); 4.60-4.40 and 3.70-3.40 (m, 2H); 2.99 and 2.87 (s + s, 3H); 2.20-1.05 ppm (s, 8H).

The synthetic route of 50910-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CORTEX PHARMACEUTICALS, INC.; WO2008/143963; (2008); A1;,
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Related Products of 671802-00-9, 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 671802-00-9 as follows.

A solution of tert-butyl 3-(2-hydroxyethoxy)propanoate (778.8 mg, 4.09 mmol, 1.00 equiv), Cs2CO3 (2.66 g, 8.16 mmol, 2.00 equiv), and 4,5-dichloro-2-[2-(trimethylsilyl)ethoxy]methyl-2,3-dihydropyridazin-3-one (1.2 g, 4.06 mmol, 1.00 equiv) in ACN (15 mL) was stirred for 3 h at 80 C. The solids were filtered and the resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with EtOAc/petroleum ether (1:1) to afford 200 mg (11%) of title compound as a white solid. LCMS: [M+H]+ 449.01.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,671802-00-9, its application will become more common.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); 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. 17100-58-2, name is (4-Bromo-2-methylphenyl)methanol. A new synthetic method of this compound is introduced below., Computed Properties of C8H9BrO

Intermediate 16: r2-methvl-4-(4,4.5,5-tetramethyl-1 ,3,2-dioxaborolan-2-vl)phenyllmethanol; A solution of intermediate 15, (4-bromo-2-methylphenyl)methanol, (30 g, 150 mmol), bis(pinacolato)diboron (40 g, 156 mmol), Pd(dppf)CI2(N) (8 g, 10 mmol), and potassium acetate (44 g, 448 mmol) in 1 ,4-dioxane (600 ml.) was heated to reflux under N2 for 4 hours. After cooling, the reaction mixture was filtered, and the filtrate was concentrated in vacuo. Purification by flash chromatography (petroleum ether/ EtOAc: 5/1 ) gave the title compound [2- methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]methanol as a red oil (34 g, 90%yield). 1H NMR (400 MHz, DMSO-d6) J7.50-7.38 (m, 3H), 5.14 (t, 1 H), 4.51 (d, 2H), 2.22 (s, 3H), 1.28 (s, 12H).

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, 17100-58-2, (4-Bromo-2-methylphenyl)methanol.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; BOUILLOT, Anne Marie Jeanne; DODIC, Nerina; GELLIBERT, Francoise Jeanne; MIRGUET, Olivier; WO2010/15652; (2010); A2;,
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