Month: January 2021

Electric Literature of 28539-02-8, 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. 28539-02-8, name is 1-(Hydroxymethyl)benzotriazole. A new synthetic method of this compound is introduced below.

To a stirred solution of n-butyllithium(1.6 M) (4.67 mL, 7.47 mmol) in anhydrous THF (15 mL) was added dropwise 2,2,6,6-tetramethylpiperidine (1.05 g, 7.47 mmol) at -10 C. The solution was allowed to stirred at 0 C for 30 minutes then cooled to -78 C. 2-((3-fluoro-2- methylphenoxy)methyl)-5-hydroxy-2-methyl-7-morpholinochroman-4-one (1.0 g, 2.49 mmol) in anhydrous THF (10 mL) was added dropwise and stirred for an additional 1 hour. 1 H-benzotriazole- methanol (0.55 g, 3.74 mmol) in anhydrous THF (20 mL) was added dropwise over a period of 30 minutes and kept 2 hours at this temperature. The reaction was quenched with Sat.NH4CI and diluted with ethyl acetate (50 mL). The organic layer was dried over Na2S04, filtered, and concentrated in vacuo. The crude compound was purified by Grace column chromatography (C-18 Reverse phase column), using 60% (0.1 % FA) acetonitrile in (0.1 % FA) water as an eluent to afford 92 (430 mg, 40%) as an off white solid. lsomer-92-1 : 1H NMR (300 MHz, DMSO-tf6):512.01 (bs, 1 H), 7.21 -7.1 1 (m, 1 H), 6.85-6.71 (m, 2H), 5.97 (d, J = 2.1 Hz, 1 H), 5.92 (d, J = 2.1 Hz, 1 H), 4.85 (t, J = 5.4 Hz, 1 H), 4.28 – 4.15 (m, 2H), 3. 87 – 3.75 (m, 2H), 3.64 (t, J = 4.5 Hz, 4H), 3.29 (t, J = 4.5 Hz, 4H), 2.91 (t, J = 5.4 Hz, 1 H), 1.95 (d, J = 1.8 Hz, 3H), 1.58 (s, 3H) lsomer-92-2: 1H NMR (300 MHz, DMSO-tf6):512.02 (bs, 1 H), 7.21 -7.1 1 (m, 1 H), 6.85-6.71 (m, 2H), 5.97 (d, J = 2.1 Hz, 1 H), 5.92 (d, J = 2.1 Hz, 1 H), 4.81 (t, J = 5.7 Hz, 1 H), 4.28 – 4.15 (m, 2H), 3. 87 – 3.75 (m, 2H), 3.64 (t, J = 4.5 Hz, 4H), 3.29 (t, J = 4.5 Hz, 4H), 2.91 (t, J = 5.4 Hz, 1 H), 1.95 (d, J = 1.8 Hz, 3H), 1.58 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,28539-02-8, 1-(Hydroxymethyl)benzotriazole, and friends who are interested can also refer to it.

Reference:
Patent; GVK BIOSCIENCES PRIVATE LIMITED; JOSHI, Hemant; DURAISWAMY, Athisayamani Jeyaraj; BETHI, Reddy Sridhar; ROY, Chowdhury Arnab; (89 pag.)WO2017/90002; (2017); A2;,
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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. 504-63-2, name is 1,3-Propanediol, molecular formula is C3H8O2, 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. Recommanded Product: 504-63-2

General procedure A: Synthesis of acetal protected aldehydes 1,3-Propanediol (1.5 eq.) and p-TSA (0.1 eq.) were added to a solution of aldehyde (5.0 mmol, 1.0 eq.) in toluene. The reaction was heated to reflux and left to stir for 7 hours. After cooling to room temperature, the reaction was washed with three portions of H2O, dried over MgSO4 and the solvent removed under reduced pressure to afford the crude acetal protected product. General procedure A was followed using 2-bromo-5-methoxybenzaldehyde (1.08 g, 5.00 mmol), to provide the title compound as an orange oil in 96% yield (1.31 g, 4.80 mmol), which was used without further purification. 1H NMR (300 MHz, CDCl3) deltaH: 7.40 (1H, d, J = 8.9 Hz, ArH), 7.24 (1H, d, J = 3.1 Hz, ArH), 6.76 (1H, dd, J = 8.8, 3.3 Hz, ArH), 5.71 (1H, s, CH), 4.28 (1H, dd, J = 5.1, 1.3 Hz, OCHAHB), 4.24 (1H, dd, J = 5.1, 1.3 Hz, OCHAHB), 4.02 (2H, td, J = 12.2, 2.5 Hz, OCH2), 3.80 (3H, s, OCH3), 2.32-2.16 (1H, m, CH2CHAHBCH2), 1.48-1.41 (1H, m, CH2CHAHBCH2); 13C{1H} NMR (75.5 MHz CDCl3) deltaC: 159.2, 138.3, 133.3, 117.2, 112.8, 112.7, 100.9, 67.7, 55.6, 25.8; I.R (thinfilm) nu max (cm-1): 1596 (ArC=C), 1575 (ArC=C); HRMS (ESI): m/z calculated for C11H13BrO3: requires: 273.0126 for [M+H]+; found: 273.0129.

With the rapid development of chemical substances, we look forward to future research findings about 504-63-2.

Reference:
Article; Peacock, Lucy R.; Chapman, Robert S. L.; Sedgwick, Adam C.; Bull, Steven D.; Mahon, Mary F.; Amans, Dominique; Organic Letters; vol. 17; 4; (2015); p. 994 – 997;,
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Related Products of 623-50-7, 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 623-50-7 as follows.

Step 1. Sodium hydride (55% dispersion in mineral oil, 603 mg, 13.8 mmol) was added to a solution of ethyl glycolate (1.43 g, 13.8 mmol) in 1,4-dioxane, and the reaction mixture was heated at 70 C. for 1 h, then 5-bromo-2-chloro-3-nitropyridine (Eur. Pat. Appl. EP 122109 (1984); 1.64 g, 6.91 mmol) was added, and stirring was continued at 70 C. for 1 h and at room temperature for 16 h. The reaction mixture was then neutralized with sat. aq. sodium hydrogencarbonate solution and extracted three times with dichloromethane. The organic layers were pooled, dried (Na2SO4), and evaporated. Chromatography (SiO2, hexane-ethyl acetate gradient) furnished (5-bromo-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (1.03 g, 49%). Light yellow liquid, MS (ISP)=305.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623-50-7, its application will become more common.

Reference:
Patent; Ackermann, Jean; Bleicher, Konrad; Ceccarelli, Simona M.; Chomienne, Odile; Mattei, Patrizio; Sander, Ulrike Obst; US2007/191603; (2007); A1;,
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Electric Literature of 127-66-2 ,Some common heterocyclic compound, 127-66-2, molecular formula is C10H10O, 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.

General procedure: The reactions were performed in a 50 ml autoclave with a Teflon vessel inside equipped with magnetic stirring under 3.0 MPa CO2. After introducing DBU (60.8 mg, 0.4 mmol), propylene glycol (76.1 mg, 1 mmol), 2-methyl-3-butyn-2-ol (126.2 mg, 1.5 mmol), DMF (2 ml), the autoclave was sealed and filled with CO2 to keep thepressure of CO2 under 3.0 MPa. Then, the reaction mixture was stirred at 120 C for 10 h. When the reaction completed, the autoclave was cooled to ambient temperature and residual CO2 was carefully released. Subsequently, the mixture was flushed with DMF and analyzed by GC using biphenyl as an internal standard.

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. 127-66-2, 2-Phenylbut-3-yn-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Han, Li-Hua; Li, Jing-Yuan; Song, Qing-Wen; Zhang, Kan; Zhang, Qian-Xia; Sun, Xiao-Fang; Liu, Ping; Chinese Chemical Letters; (2019);,
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Application of 932-01-4, 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.932-01-4, name is 4,4-Dimethylcyclohexanol, molecular formula is C8H16O, molecular weight is 128.21, as common compound, the synthetic route is as follows.

Method B: To a solution of 7-nitrophthalazin-l(2H)-one (Intermediate- 10, step-1 , 355 mg, 1.858 mmol) and 4,4-dimethylcyclohexanol (356 mg, 2.78 mmol) in THF (6 mL) were added PPh3 (1.22 g, 4.64 mmol) and diisopropyl azodicarboxylate (1.12 g, 5.57 mmol) and the reaction mixture was heated at reflux for 4 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 300 mg of the title product.

The chemical industry reduces the impact on the environment during synthesis 932-01-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/72825; (2013); A1;,
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Reference of 702-82-9, Adding some certain compound to certain chemical reactions, such as: 702-82-9, name is 3-Aminoadamantan-1-ol,molecular formula is C10H17NO, 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 702-82-9.

EXAMPLESExample 1-1 (General procedure (A))4-(2,4-Dichloro-phenoxy)-N-((1 R,3S,5R,7S)-3-hvdroxy-adamantan-1-yl)-butyramideTo a stirred solution of 4-(2,4-dichloro-phenoxy)-butyric acid (0.8 g, 3.21 mmol) in dry THF (25 mL) was added HOBt (0.48 mg, 3.533 mmol) and EDAC (0.68 g, 3.533 mmol). After stirring for 10 min. at room temperature, DIPEA (0.62 mL) and 3-amino-adamantan-1- ol (0.59 g, 3.533 mmol) were added and the resulting mixture was stirred for 16 hrs. at room temperature. The volatiles were removed in vacuo and to the residue was added water (25 mL) followed by extraction with EtOAc (3×35 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The oily residue was crystallised from diethyl ether (5 mL) affording after drying at 50 0C in vacuo 800 mg (62 %) of the title compound as a solid. 1H NMR (400 MHz, DMSO-c/6) delta 1.35 – 1.58 (m, 6H), 1.70 – 1.85 (m, 6H), 1.91 (q, 2H) 2.09 (br.s., 2H), 2.21 (t, 2H), 4.04 (t, 2H), 4.48 (br.s., 1 H), 7.15 (d, 1 H), 7.36 (dd, 1 H), 7.40 (br.s., 1 H), 7.57 (d, 1 H).

According to the analysis of related databases, 702-82-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TRANSTECH PHARMA, INC.; NOVO NORDISK A/S; WO2008/134221; (2008); A1;,
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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.100-37-8, name is 2-(Diethylamino)ethanol, molecular formula is C6H15NO, molecular weight is 117.1894, as common compound, the synthetic route is as follows.HPLC of Formula: C6H15NO

A mixture of 3-[6-(7-chloro-4-oxo-4H-1,3-benzothiazin-2-yl)-4-(methylsulfonyl)pyridin-2-yl]prop anoic acid (0.21 g, 0.5 mmol), N,N-diethylethanolamine (0.12 g, 1.0 mmol), HOBt H2O (92 mg, 0.6 mmol), WSC (116 mg, 0.6 mmol), 4-dimethylaminopyridine (74 mg, 0.6 mmol) and DMF (3 ml) was stirred at room temperature for 18 hours. Water (20 ml) was added to the reaction mixture and the crystals formed were taken by filtration. The crystals were recrystallized from ethanol to give the title compound (0.13 g, 50%). Melting point: 150.5-151.5C 1H-NMR (CDCl3) delta: 1.02 (6H, t, J=7.2 Hz), 2.57 (4H, q, J=7.2 Hz), 2.71 (2H, t, J=6.3 Hz), 3.04 (2H, t, J=7.2 Hz), 3.16 (3H, s), 3.39 (2H, t, J=7.2 Hz), 4.20 (2H, t, J=6.3 Hz), 7.60-7.67 (2H, m), 7.98 (1H, s), 8.50 (1H, d, J=8.4 Hz), 8.80 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-37-8, 2-(Diethylamino)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1897880; (2008); A1;,
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Reference of 7218-43-1, Adding some certain compound to certain chemical reactions, such as: 7218-43-1, name is 2-[2-(2-Propynyloxy)ethoxy]ethanol,molecular formula is C7H12O3, 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 7218-43-1.

Weigh 1g of compound 44 in 50mL of dichloromethane, add 1.4g of triethylamine and 2.1g of p-nitrophenyl chloroformate, stir overnight at room temperature, and concentrate by column chromatography to obtain 603mg of compound 45, yield 28.1% .

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. 7218-43-1, 2-[2-(2-Propynyloxy)ethoxy]ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenzhen Tagete Bio-pharmaceutical Technology Co., Ltd.; Xie Yongmei; Zhao Yu; Luo Bo; (38 pag.)CN110845559; (2020); A;,
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Related Products of 56456-49-6 ,Some common heterocyclic compound, 56456-49-6, molecular formula is C7H6ClFO, 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 a solution of 2,3,5-trifluoropyridine (1.5 g, 11 mmol) and 4-chloro-2-fluorobenzyl alcohol (1.81 g, 11.3 mmol) in NMP (20 mL) was added K2CO3 (4.67 g, 33.8 mmol) at 25 C. and the mixture was stirred at 100 C. for 16 h. The mixture was poured into water (30 mL) and then extracted with EtOAc (3*50 mL). The combined organic extracts were washed with brine (3*40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (0 to 5% EtOAc/PE gradient) to give 2-((4-chloro-2-fluorobenzyl)oxy)-3,6-difluoropyridine (2.45 g, 80%) as a colorless oil. 1H NMR (CDCl3) delta 7.41-7.54 (m, 2H), 7.11-7.20 (m, 2H), 6.47 (ddd, 1H), 5.44 (s, 2H).

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. 56456-49-6, 4-Chloro-2-fluorobenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; Aspnes, Gary Erik; Bagley, Scott W.; Curto, John M.; Dowling, Matthew S.; Edmonds, David; Flanagan, Mark E.; Futatsugi, Kentaro; Griffith, David A.; Huard, Kim; Ingle, Gajendra; Jiao, Wenhua; Limberakis, Chris; Mathiowetz, Alan M.; Piotrowski, David W.; Ruggeri, Roger B.; (73 pag.)US2018/170908; (2018); A1;,
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Related Products of 445-26-1, 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. 445-26-1, name is 1-(2-Fluorophenyl)ethanol. A new synthetic method of this compound is introduced below.

To a solution of ethyl 2-fluoro-4-iodonicotinate (0.70 g) obtained by a known method (Organic Letters, 7(10), 1943-1946; 2005) and 1-(2-fluorophenyl)ethanol (0.50 g) in THF (7 mL) was added 60% sodium hydride (0.14 g) at 0C, and the mixture was stirred at the same temperature for 1 hr. To the reaction solution was added water at 0C, and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (0.77 g). 1H NMR (300 MHz, CDCl3) delta 1.42 (3H, t, J = 7.1 Hz), 1.61 (3H, d, J = 6.6 Hz), 4.47 (2H, q, J = 7.2 Hz), 6.48 (1H, q, J = 6.5 Hz), 6.94-7.14 (2H, m), 7.17-7.24 (1H, m), 7.25-7.30 (1H, m), 7.41 (1H, td, J = 7.5, 1.6 Hz), 7.73 (1H, d, J = 5.5 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,445-26-1, 1-(2-Fluorophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
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