Month: August 2021

Electric Literature of 6153-05-5, Adding some certain compound to certain chemical reactions, such as: 6153-05-5, name is (Z)-3-Methylpent-2-en-4-yn-1-ol,molecular formula is C6H8O, 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 6153-05-5.

n-BuLi (4.2 mL, 10 mmol, 2.4 mol/L) was added dropwise to a solution of (Z)-3-methylpent-2-en-4-yn-1-ol (0.48 g, 5 mmol) in THF (10 mL) at ?78 °C under a N2 atmosphere, and then the mixturewas stirred for 1 h at ?78 °C. A solution of 4g (0.94 g, 5 mmol) in THF (5 mL) was added slowly, themixture was stirred for 0.5 h at ?78 °C, and then it was warmed to room temperature and stirred for 2 h.The reaction was quenched with saturated aqueous NH4Cl solution (10 mL) and extracted with EtOAc(3 × 30 mL). The combined organics were washed with brine (2 × 20 mL), dried over anhydrousNa2SO4 and concentrated. The residue was purified by silica gel column chromatography (petroleumether/EtOAc, 1:2) to afford 6c (1.35 g, 95percent) as a yellow oil.

According to the analysis of related databases, 6153-05-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Xiaoqiang; Wan, Chuan; Yang, Dongyan; Yuan, Xiaoyong; Du, Shijie; Xiao, Yumei; Qin, Zhaohai; Molecules; vol. 18; 9; (2013); p. 10776 – 10788;,
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Electric Literature of 558-42-9 , The common heterocyclic compound, 558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, 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.

To 3-bromo-5-fluoro-phenol (9.0 g, 47 mmol), and 1-chloro-2-methyl-propan-2-ol (5.116 g, 47.12 mmol), aqueous sodium hydroxide (37.69 g, 94.24 mmol) was added and the reaction mixture was heated at 120° C. for 5 days in a pressure vessel. The reaction was cooled and then extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified on 220 g of silica gel utilizing a gradient of 0 to 10percent ethyl acetate in dichloromethane. The impure product was repurified on 220 g of gold silica gel utilizing a gradient of 0 to 10percent ethyl acetate in dichloromethane to yield 1-(3-bromo-5-fluoro-phenoxy)-2-methyl-propan-2-ol (4.75 g, 18.0 mmol, 38percent). ESI-MS m/z calc. 262.00046. found 263.0 (M+1)+. Retention time: 1.57 minutes (3 min run).

The synthetic route of 558-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
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Electric Literature of 61439-59-6, 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. 61439-59-6, name is 2-(4-(Benzyloxy)phenyl)ethanol. A new synthetic method of this compound is introduced below.

Take 10.0 mL ionic liquid [Emim] [OSO2OE],Add 1.0 g (4.1 mmol) 4-phenoxyphenylethanol and 2.4 g (4.9 mmol) 2,3,4,6-tetra-O-acetyl-?[-0-glucopyranose trichloroacetimidate ,Nitrogen gas three times,Cool to 0 ° C,75 muL of TMSOTf (0.4 mmol) was added dropwise using a microsyringe.Keep the temperature at around 0 °C for about 0.5 hours.Then slowly increase to room temperature for 2 h.TLC detects the disappearance of alcohol raw materials,The reaction was quenched with triethylamine.The reaction solution was extracted with anhydrous diethyl ether to give the resulting glycoside.Combine the ether phase,Use a small amount of 4percent Na2CO3,Washed with saturated saline,Then add 4percent Na2SO4 to dry,The ether was removed by rotary evaporation and recrystallized from ethanol-cyclohexane to give 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-tetra-O-acetyl)-alpha-D-pyridin Glucosinolate1.83 g, milky white solid product, yield 80.1percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,61439-59-6, its application will become more common.

Reference:
Patent; Zaozhuang College; Zhou Fengyan; Zhang Wenzhi; Kong Xiaoyu; Yuan Yaru; Li Suwan; (12 pag.)CN107880085; (2018); A;,
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Electric Literature of 111-46-6, 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. 111-46-6, name is 2,2′-Oxybis(ethan-1-ol), molecular formula is C4H10O3, 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 2-(2-hydroxyethoxy)ethanol (55.66 g, 524.53 mmol, 49.70 mL, 2 eq) in tetrahydrofuran (500 mL) was added sodium hydride (6.29 g, 157.27 mmol, 60% purity, 0.6 eq) at 0 C and stirred for 0.5 hour under nitrogen. Then the mixture was added p- toluenesulfonyl chloride (50 g, 262.26 mmol, 1 eq), warmed to 25 C and stirred for 6 hours. The mixture was poured into saturated ammonium chloride solution (200 mL) and stirred for 15 minutes. The aqueous phase was extracted with ethyl acetate (200 mL x 2). The combined organic phase was washed with brine (200 mL), dried with anhydrous anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (Petroleum ether/Ethyl acetate=l0/l to 1/1) to afford 2-(2-hydroxyethoxy)ethyl 4- methylbenzenesulfonate (35 g, 134.46 mmol, 51 % yield) as a yellow oil. LC/MS (ESI) m/z. 261.0 [M+l] +; 1H-NMR (400MHz, CDCb) d 7.76 – 7.72 (m, 2H), 7.28 (d, / = 8.0 Hz, 2H), 4.15 – 4.02 (m, 2H), 3.66 – 3.55 (m, 4H), 3.49 – 3.44 (m, 2H), 2.38 (s, 3H).

According to the analysis of related databases, 111-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; DONG, Hanqing; BERLIN, Michael; CREWS, Craig M.; (1213 pag.)WO2019/195609; (2019); A2;,
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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. 18068-06-9, name is 4-Methoxycyclohexanol. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 18068-06-9

The residue was dissolved in DCM (2.0 ml_), cooled to 0 C under nitrogen atmosphere, and then methanesulfonyl chloride (0.18 ml_, 2.39 mmol) and triethylamine (0.42 ml_, 2.98 mmol) were added succesively. The reaction mixture was stirred at 0 C for 1 h, and then quenched with water (20 ml_). The aqueous layer was extracted with DCM (3 x 10 ml_). The organic extracts were combined, filtered over a hydrophobic fit and concentrated under reduced pressure to provide (4- methoxycyclohexyl) methanesulfonate (320 mg, 1 .55 mmol, 78% yield) as a yellow oil.

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, 18068-06-9, 4-Methoxycyclohexanol.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (191 pag.)WO2017/46604; (2017); A1;,
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Synthetic Route of 517-21-5, 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. 517-21-5, name is Sodium 1,2-dihydroxyethane-1,2-disulfonate, molecular formula is C2H4Na2O8S2, 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.

Zinc powder (1.1 g, 19 mmol) was added to a mixture of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-iodo-2-(morpholine-4-carbonyl)-phenyl]amide (1.0 g, 1.9 mmol) and AcOH (20 mL), and the resulting mixture was heated at 50 C. for 1 h with vigorous stirring. The mixture was filtered through a pad of diatomaceous earth, rinsing well with methanol, and the clear solution was concentrated to a yellow solid. This material was dissolved in methanol (20 mL) and added to a mixture of glyoxal sodium bisulfite adduct (1.5 g, 5.7 mmol), AcOH (0.85 mL), NaOAc (0.16 g, 2.0 mmol), and H2O (6 mL). The reaction was allowed to proceed under reflux for 3 h, then was diluted with EtOAc (200 mL) and filtered through a pad of diatomaceous earth, rinsing well with EtOAc. The filtrate was washed with H2O (100 mL) and brine (100 mL), then was dried and concentrated to a yellow solid. Purification by flash chromatography gave the titled compound as a light yellow solid (0.69 g, 70%).

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 517-21-5, Sodium 1,2-dihydroxyethane-1,2-disulfonate.

Reference:
Patent; Allison, Brett D.; Hack, Michael D.; Phuong, Victor K.; Rabinowitz, Michael H.; Rosen, Mark D.; US2005/38032; (2005); 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. 2612-28-4, name is 2-Propylpropane-1,3-diol, molecular formula is C6H14O2, 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. Application In Synthesis of 2-Propylpropane-1,3-diol

(2-1) under a nitrogen atmosphere, 4-bromo-3-fluorobenzaldehyde (20.0g), 2- propyl-1,3-propanediol (11.6g) and p-toluenesulfonic acid monohydrate (0.9g ) was dissolved in toluene (100mL), while using the Dean-Stark apparatus at reflux of the solvent while removing the formed water was stirred for 4 hours. After cooling, saturated aqueous sodium bicarbonate solution (100 mL) were separated, washed with saturated brine (100 mL) and the organic layer was washed, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography was purified to give crude 2- (4-bromo-3-fluorophenyl) -5-propyl-1,3-dioxane (31.0g) .

With the rapid development of chemical substances, we look forward to future research findings about 2612-28-4.

Reference:
Patent; DIC Corporation; Tojo, Kenta; Tetsuo, Kusumoto; (46 pag.)CN105358538; (2016); A;,
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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. 626-18-6, name is 1,3-Benzenedimethanol. This compound has unique chemical properties. The synthetic route is as follows. name: 1,3-Benzenedimethanol

Example 4Dimer 18 (IGN-Ol):[221] To a stirred solution of 1,3-Benzenedimethanol 16 (11 mg, 0.08 mmol) in anhydrous dichloromethane (0.8 rnL) was added triethylamine (33 mul, 0.24 mmol) then methanesulfonyl chloride (16 muL, 0.21 mmol) dropwise in 15 minutes at -5 ~ -10 0C. The solution was stirred at – 5 – 10 0C for another 60 minutes and was quenched with ice/water, diluted with cold ethyl acetate. The mixture was separated and the organic layer was washed with cold water, dried over anhydrous sodium sulfate. It was filtered and the filtrate was evaporated by rotary evaporation in vacuo (temperature <; 35 0C). The residue 17 was high vacuumed for a few hours before being dissolved in anhydrous DMF (1.5 mL). IBD monomer 7 (94 mg, 0.32 mmol), anhydrous potassium carbonate (50 mg, 0.36 mmol) and potassium iodide (27 mg, 0.16 mmol) were added subsequently. The mixture was stirred at room temperature for 17 hours (checked by mass spectrum) and diluted with dichloromethane. It was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by reverse phase HPLC (C 18 column, CH3CN/H2O, loaded column with CH3CN/H2O, 3:1, stirred for 30 min and centrifuged before injection) to furnish dimer 18 (IGN- 01, 6.6 mg) as a white solid. 1R NMR (400 MHz, CDCl3): delta 8.21 (d, J = 8.0 MHz, 2H), 7.79 (d, J = 4.4 MHz, 2H), 7.51 (s, 2H), 7.46 (s, IH), 7.36 (bs, 3H), 7.23-7.18 (m, 4H), 7.06-7.03 (m, 2H), 6.79 (s, 2H), 5.20 (d, J = 12.4 MHz, 2H), 5.14 (d, J = 12.4 MHz, 2H), 4.41 (ddd, Jl = 10.8 MHz, J2 = 4.4 MHz, J3 = 4.0 MHz, 2H), 3.92 (s, 6H), 3.64 (dd, Jl = 17.2 MHz, J2 = 11.2 MHz, 2H), 3.42 (dd, Jl = 16.8 MHz, J2 = 4.0 MHz, 2H); HRMS (ESI, m/z): calc. 691.2557 (M + H)+, found 691.2570. Example 5Dimer 19 (IGN-02):[222] To a stirred solution of 1,3-Benzenedimethanol 16 (10 mg, 0.074 mmol) in anhydrous dichloromethane (0.8 rnL) was added triethylamine (31 mul, 0.22 mmol) then methanesulfonyl chloride (15 muL, 0.19 mmol) dropwise in 15 minutes at -5 ~ -10 0C. The solution was stirred at - 5 - 10 0C for another 60 minutes and was quenched with ice/water, diluted with cold ethyl acetate. The mixture was separated and the organic layer was washed with cold water, dried over anhydrous sodium sulfate. It was filtered and the filtrate was evaporated by rotary evaporation in vacuo (temperature <; 35 0C). The residue 17 was high vacuumed before dissolving in anhydrous DMF (1.5 rnL). OBD monomer 14 (70 mg, 0.28 mmol), anhydrous potassium carbonate (51 mg, 0.37 mmol) and potassium iodide (25 mg, 0.15 mmol) were added subsequently. The mixture was stirred at room temperature for 17 hours (checked by mass spectrum) and diluted with dichloromethane. It was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by reverse phase HPLC (C 18 column, CH3CN/H2O, loaded column with CH3CN/H2O, 3:1, stirred for 30 min and centrifuged before injection) to furnish dimer 19 (IGN- 02, 10.0 mg) as a white solid. 1H NMR (400 MHz, CDCl3): delta 7.75 (d, J = 4.0 MHz, 2H), 7.50-7.48 (bs, 3H), 7.38 (bs, 3H), 6.83 (s, 2H), 5.26 (d, J = 5.2 MHz, 2H), 5.21 (d, J = 14.4 MHz, 2H), 5.15 (d, J = 14.0 MHz, 2H), 5.03 (d, J = 5.6 MHz, 2H), 4.34-4.30 (m, 2H), 3.94 (s, 6H), 3.86-3.76 (m, 2H); HRMS (ESI, m/z): calc. 599.2142 (M + H)+, found 599.2184. 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, 626-18-6, 1,3-Benzenedimethanol. Reference:
Patent; IMMUNOGEN, INC.; LI, Wei; FISHKIN, Nathan, Elliott; ZHAO, Robert, Yongxin; MILLER, Michael, Louis; CHARI, Ravi, V., J.; WO2010/91150; (2010); 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. 2503-56-2, name is 7-Hydroxy-5-methyl-1,3,4-triazaindolizine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6N4O

The proper 5- Methyl-[1,2,4] triazolo [1,5-a] Pyrimidin-7-ol (10 mmol) was added to 2.75 ml (30 mmol) of phosphorous oxychloride and heated under reflux for 90 min in a round bottom flask. Excess phosphorous oxychloride was removed by distillation at reduced pressure on a steam bath, and the residue was triturated with ice water. The product was extracted from the aqueous mixture with CH2Cl2, evaporated, and purified by column chromatography using 60% EtOAc/hexane. Yield of the product is 55%. 4.1.4.1. 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine (8). White-yellow solid (Rf = 0.6 in pure ethyl acetate); m.p. 150 C.; 1H NMR (300 MHz, CDCl3): delta 8.50 (s, 1H, Triazolopyrimidine-Hb), 7.15 (s, 1H, Triazolopyrimidine-Ha), 2.75 (s, 3H, Triazolopyrimidine-CH3)LCMS: (ESI, m/z): [M+H]+ calcd for C5H6ClN4 169.1; found: 169.1.

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, 2503-56-2, 7-Hydroxy-5-methyl-1,3,4-triazaindolizine.

Reference:
Article; Kumar, Jitendra; Meena, Poonam; Singh, Anju; Jameel, Ehtesham; Maqbool, Mudasir; Mobashir, Mohammad; Shandilya, Ashutosh; Tiwari, Manisha; Hoda, Nasimul; Jayaram; European Journal of Medicinal Chemistry; vol. 119; (2016); p. 260 – 277;,
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Electric Literature of 1072-52-2 ,Some common heterocyclic compound, 1072-52-2, molecular formula is C4H9NO, 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 5 (Table 1, entry 2, and Scheme 6). Preparation of 2-[2-(aminocarbonyl)(2- bromoethyl)-4,6-dinitroanilino] ethyl methanesulfonate (13b); A slurry of 2-chloro-3,5- dinitrobenzamide (U) (237 mg, 1.1 mmol) in dry 3-methyl-2-butanone (20 mL) was cooled to below 5 0C, and LiBr (1.5 g) was added, keeping the temperature below 15 0C. Aziridineethanol (240 mg, 2.76 mmol) was added to the stirred mixture, which was then kept at 20 0C overnight. Water (50 mL) was added, followed by EtOAc (100 mL). The organic layer was washed with water, 10% aqueous NaBr, and then passed through a short column of silica gel, eluting with heptane/EtOAc (1:1), to give 2-[(2-bromoethyl)(2-hydroxyethyl)amino]-3,5- dinitrobenzamide (12b) (360 mg, 87%) as a yellow solid: mp (EtOAc/petroleum ether) 138- 140 C; 1H NMR [(CD3)2SO] delta 8.69 (dj = 2.8 Hz, 1 H), 8.43 (s, 1 H), 8.35 (dj = 2.8 Hz, 1 H), 8.10 (s, 1 H), 5.15 (t, / = 5.6 Hz, 1 H), 3.61 (m, 4 H), 3.53 (m, 2 H), 3.14 (m, 2 H); 13C NMR delta 167.6, 146.4, 143.8, 139.8, 134.2, 128.2, 123.0, 57.8, 54.1, 53.6, 29.8; Anal. Calcd for C11H13BrN4O6: C, 35.0; H, 3.5; N, 14.9. Found: C, 35.0; H, 3.5; N, 14.6%.

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. 1072-52-2, 2-(Aziridin-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2008/30112; (2008); A1;,
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