Tag: M.W=100-200

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 5020-41-7, 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. 5020-41-7, name is 2-(3-Methoxyphenyl)ethanol, molecular formula is C9H12O2, 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.

(i) 2-(2-Bromo-5-methoxyphenyl)ethanol To a stirred mixture of 3-methoxyphenethyl alcohol (1.18 g, 7.8 mmol) and pyridine (0.75 ml, 9.3 mmol) in dry dichloromethane (10 ml) was added bromine (0.47 ml, 18.0 mmol) dropwise under nitrogen at 0 C. The orange solution was stirred at room temperature for 4 hours (hr). The reaction mixture was quenched by the addition of 10% sodium bisulfite aqueous solution., and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate, and concentrated to give crude products, which were purified by silica-gel column chromatography eluted with gradient of hexane and ethyl acetate (10:1, 8:1, 5:1) to give the title compound as a colorless oil (1.5 g, 83.2%). 1H-NMR (CDCl3): 7.43 (d, J=8.8 Hz, 1H), 6.83 (d, J=3.3 Hz, 1H), 6.67 (dd, J=8,8, 3.3 Hz, 1H), 3.91-3.81 (m, 2H), 3.78 (s, 3H), 2.99 (t, J=6.6 Hz, 2H).

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 5020-41-7, 2-(3-Methoxyphenyl)ethanol.

Reference:
Patent; Pfizer INC; US6239147; (2001); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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 100058-61-5, name is 3-(Benzyloxy)cyclobutanol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-(Benzyloxy)cyclobutanol

DEAD (1.35 mL, 5.73 mmol) was added dropwsie to a solution of crude product (1s,3s)-3-(benzyloxy)cyclobutan-1-ol (1.02 g, 5.73 mmol), 3,4-difluorophenol (821 g, 6.3 mmol) and triphenylphosphine (2.26 g, 8.6 mmol) in dry tetrahydrofuran (20 mL) at 0 C. The reaction mixture was placed under nitrogen atmosphere and stirred at 80 C for 15 h. The solvent was removed under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 80:1 as eluent) to get 4-(anti-3-(benzyloxy)cyclobutoxy)-1,2-difluorobenzene (1.116 g, 68% two step yield) as faint yellow oil. 1H NMR (300 MHz, CDCl3) delta 7.39-7.25 (m, 5H), 7.08-6.99 (m, 1H), 6.63-6.56 (m, 1H), 6.51-6.44 (m, 1H), 4.81-4.73 (m, 1H), 4.44 (s, 2H), 4.36-4.28 (m, 1H), 2.54-2.37 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 100058-61-5.

Reference:
Article; Sheng, Ren; Yang, Liu; Zhang, Yanchun; Xing, Enming; Shi, Rui; Wen, Xiaoan; Wang, Heyao; Sun, Hongbin; Bioorganic and Medicinal Chemistry Letters; vol. 28; 15; (2018); p. 2599 – 2604;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 3840-31-1, 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 3840-31-1, name is (3,4,5-Trimethoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of commercially available (3,4,5-trimethoxyphenyl)methanol (25 g, 126 mmol) in THF (150 mL) was added sodium hydride (3.93 g, 164 mmol) portion-wise at 0 C and the reaction mixture was stirred at 0 C (10 minutes). Iodomethane (10.2 mL, 164 mmol) was then added drop-wise and the resulting mixture was allowed to come to room temperature with stirring (3 h). The reaction was quenched by pouring into ice, extracted (EtOAc), washed with brine, dried (Na2SO4), filtered and concentrated and the resulting residue was purified by silica gel column chromatography to provide 6f as a colorless oil (26.44 g, 125 mmol, 99 % yield).

According to the analysis of related databases, 3840-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Xue Zhi; Maddali, Kasthuraiah; Smith, Steven J.; Metifiot, Mathieu; Johnson, Barry C.; Marchand, Christophe; Hughes, Stephen H.; Pommier, Yves; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7309 – 7313;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 104-38-1, 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 104-38-1, name is 1,4-Bis(2-hydroxyethoxy)benzene. This compound has unique chemical properties. The synthetic route is as follows.

Example 13 {2-[4-(2-Carboxymethoxy-ethoxy)-phenoxy]-ethoxy}-acetic acid To a suspension of sodium hydride (60%, 132 grams, 3.30 moles) in anhydrous dimethylformamide (600 mL) under nitrogen atmosphere at 0 C. was added hydroquinone bis ethanol (150 grams, 756.7 mmoles) in small for hour, later stirred at room temperature for one hour. To the above mixture was added a solution of chloro acetic acid (195 grams, 2.06 moles) in anhydrous dimethylformamide (300 mL) very cautiously drop wise as the reaction is exothermic. Later the reaction is maintained at 80 C. for one hour and left at room temperature for 16 hours. Reaction mixture carefully poured onto ice (3 kg), extracted with ethyl acetate (2*500 mL) and organic phase discarded. The pH of the aqueous layer was adjusted to 2 with 3N-hydrochloric acid and extracted into ethyl acetate. The ethyl acetate extract was dried over sodium sulphate followed by distillation to yield crude 13 (120 grams, 50.5%) which was carried over to next stage. 1H NMR (CDCl3) delta 3.84 (m, 2H, CH2), 4.06 (m, 4H, CH2*2), 6.82 (s, 2H, Ar).

According to the analysis of related databases, 104-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bezwada Biomedical, LLC; US8053591; (2011); B2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts