Month: January 2021

Synthetic Route of 37585-16-3, 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.37585-16-3, name is (2-Amino-4-chlorophenyl)methanol, molecular formula is C7H8ClNO, molecular weight is 157.6, as common compound, the synthetic route is as follows.

4-chloro-2- (3-fluoro-benzyloxy)-7-methoxy-quinazoline (3.18, 10 mmol) and 4-chloro-2-amino-benzyl alcohol (1.57 g, 10 mmol) were dissolved in isopropanol (30 ml) to form a solution, and phosphoric acid (0.20 ml) was added dropwise to the solution. The reaction was carried out according to General Method I for preparing the intermediate III to obtain a white solid intermediate M-35 (3.83 g, 80.63%).

The chemical industry reduces the impact on the environment during synthesis 37585-16-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shenzhen Salubris Pharmaceuticals Co., Ltd.; Shanghai Institute of Pharmaceutical Industry; LI, Jianqi; ZHANG, Zixue; XIE, Peng; ZHANG, Qingwei; EP2592083; (2013); A1;,
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Reference of 108343-90-4 , The common heterocyclic compound, 108343-90-4, name is 2-Amino-2-(2-methoxyphenyl)ethanol, molecular formula is C9H13NO2, 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.

In a 250-ml triple-neck flask, 4.2 g (25 mmol) of 2-amino-2-(2-methoxyphenyl)ethanol obtained previously and 2.5 g (25 mmol) of KHCO3 are solubilized in 40 ml of water. After 10 min of stirring, it cooled to 0 C. and 3.4 g (25 mmol) of K2CO3, are added and then 17 ml (32.6 mmol) of 20% phosgene in toluene are added dropwise. The medium is stirred at 0 C. for 6 h. The formation of a white product is observed, which is filtered and dried. 3.6 g (18.6 mmol) of 4-(2-methoxyphenyl)oxazolidin-2-one are recovered in the form of a white solid. Yield: 75% . 1H NMR (CDCl3) delta: 3.85 (s, 3H); 4.18 (dd, 1H, J=8.8 and 6.4 Hz); 4.80 (m, 1H); 5.25 (dd, 1H, J=8.6 and 6.4 Hz); 5.46 (is, 1H); 6.90 (m, 1H); 7.01 (m, 1H); 7.32 (m, 2H).

The synthetic route of 108343-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; SOKOLOFF, Pierre; MAILLOS, Philippe; CUISIAT, Florence; VIDALUC, Jean-Louis; IMBERT, Thierry; US2015/336943; (2015); A1;,
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Electric Literature of 111-46-6, 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 111-46-6, name is 2,2′-Oxybis(ethan-1-ol). This compound has unique chemical properties. The synthetic route is as follows.

Sodium metal (64 mg, 0.03 eq) was added to a solution of diethylene glycol (29.5 g, 0.278 mmol) in THF (100 mL). The mixture was stirred for 1 hour to dissolve the sodium, then /cvV-butyl acrylate (12.4 g, 97 mmol) was added. The resulting mixture was stirred for 2 days, then concentrated under reduced pressure and the residue purified by silica chromatography (1 : 1 hexane:EtOAc) to give the title compound (9.1 g, 40%) as a colorless oil. (0315) [00139] NMR (400 MHz, CDCb): d 3.75 (m, 4H), 3.64 (m, 6H), 2.53 (t, 2H), 2.40 (s, 1H), (0316) 1.45 (s, 9H).

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; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; SCOTT, David; LI, Zhengnian; PINCH, Benika J.; OLSON, Calla; FISCHER, Eric S.; NOWAK, Radoslaw P.; DONOVAN, Katherine A.; (171 pag.)WO2020/69105; (2020); A1;,
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Electric Literature of 20712-12-3, 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 20712-12-3 as follows.

Step 2: Synthesis of 2-amino-5-bromobenzaldehyde A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and Mn02 (25.8 g, 296.6 mmol) in CH2C12 (400 mL) was stuffed at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the titlecompound as a light yellow solid (8 g, 8 1percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [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,20712-12-3, its application will become more common.

Reference:
Patent; BLUEPRINT MEDICINES; BIFULCO, Neil, Jr.; BROOIJMANS, Natasja; HODOUS, Brian, L.; KIM, Joseph, L.; MIDUTURU, Chandrasekhar, V.; WO2014/11900; (2014); A2;,
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Synthetic Route of 6329-73-3, 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 6329-73-3 as follows.

Step 2; To a cold (ice water) suspension of sodium hydride (316 mg; 7.9 mmol) in anhydrous DMF (10 mL) is added a solution of the previous alcohol (1.31 gm; 7.9 mmol) in anhydrous DMF (5 mL) over 10 minutes. After allowing to room temperature over 30 minutes, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (1 gm; 7.2 mmol) in anhydrous DMF (15 mL), and allowed to room temperature overnight. The reaction mixture is poured into ice water with vigorous stirring and extracted with ethyl acetate. The organics are separated, washed with brine, dried over magnesium sulfate, and the solvent is removed to give 2.22 grams 2-(1-benzo[1,3]dioxol-5-yl-ethoxy)-6-fluorobenzonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6329-73-3, its application will become more common.

Reference:
Patent; DECODE CHEMISTRY, INC.; SINGH, Jasbir; GURNEY, Mark E.; WO2005/123724; (2005); A1;,
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Application of 17773-10-3 ,Some common heterocyclic compound, 17773-10-3, molecular formula is C5H14INO, 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.

Intermediate 39 (150 mg, 0.15 mmol) was dissolved in DCM (4 ml) and hydroxyethyltrimethyl-ammonium iodide (173 mg, 0.75 mmol), EDC (86 mg, 0.45 mmol) and DMAP (55 mg, 0.45 mmol) were added. The mixture was stirred at RT for 7 h and water (4 ml) was added. The aqueous layer was separated and evaporated. Purification was achieved using HPLC system 3.Yield: 35 mg (16%)LC-MS (Method 1): Rt 6.78 min, m/z 585.80 [M2+]/2

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. 17773-10-3, Choline Iodide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARGENTA DISCOVERY LTD; WO2006/82412; (2006); A2;,
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Electric Literature of 2173-69-5, 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 2173-69-5 as follows.

To a solution of 2-methyl-2-phenyl-propan-1-ol (13.3 g, 87.0 mmol) in DMSO (150 mL) was added triethylamine (24.7 mL, 178.0 mmo) at rt, followed by pyridine sulfuric oxide (28.6 g, 180.0 mmol). The mixture was stirred for 2.5 h at rt. Water was added and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product 2-methyl-2-phenyl- propionaldehyde (12.0 mg, 91.6 %), which was used to the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2173-69-5, its application will become more common.

Reference:
Patent; NOVO NORDISK A/S; WO2008/84044; (2008); A1;,
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Electric Literature of 100058-61-5, 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 100058-61-5 as follows.

Step 1: 4-((1r,3r)-3-(benzyloxy)cyclobutoxy)pyridine To a solution of pyridin-4-ol (3.20 g, 33.66 mmol, 1.5 eq) and 3-benzyloxycyclobutanol (4 g, 22.44 mmol, 1 eq) in tetrahydrofuran (200 mL) was added triphenylphosphine (7.06 g, 26.93 mmol, 1.2 eq) and diisopropyl azodicarboxylate (5.45 g, 26.93 mmol, 1.2 eq) in one portion at 10 C. under nitrogen. The mixture was stirred at 50 C. for 12 hours. The reaction mixture was concentrated under reduced pressure to remove tetrahydrofuran. Water (50 mL) was poured into the mixture and stirred for 1 minute. The aqueous phase was extracted with dichloromethane (50 mL*3). The combined organic phase was washed with brine (50 mL*2), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography (petroleum ether: tetrahydrofuran from 20:1 to 5:1). HPLC showed 41% of the product in 254 mm. The residue was purified by flash C18 column chromatography [acetonitrile: water (0.5% ammonium hydroxide)=5%-50%]. Compound 4-(3-benzyloxycyclobutoxy) pyridine (3.2 g, 12.53 mmol, 55% yield) was obtained as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100058-61-5, its application will become more common.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
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Electric Literature of 1261524-75-7, 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.1261524-75-7, name is 3-Bromo-2-chlorobenzyl Alcohol, molecular formula is C7H6BrClO, molecular weight is 221.48, as common compound, the synthetic route is as follows.

Step D: 5-bromo-4-chloro-2-benzofuran-l(3H)-one: To a flask charged with (3-bromo-2- chlorophenyl)methanol (1.1 g, 4.8 mmol) and a stir bar was added thallium trifluoroacetate (2.9 g, 5.3 mmol) and TFA (6 mL). The mixture was allowed to stir at RT for 16 hours. The volatiles were removed under reduced pressure. The residue was pumped under high vacuum for 15 minutes before palladium (II) chloride (0.085 g, 0.48 mmol), magnesium oxide (0.39 g, 9.6 mmol), lithium chloride (0.20 g, 4.8 mmol), and ethanol (30 mL) were added. The mixture was stirred under an atmosphere of carbon mono-oxide until the reaction turned black. The reaction was diluted with DCM. The suspension was filtered through a pad of celite to remove the solids. The filtrate was adsorbed onto silica gel, and purified by MPLC to afford the title compound.

Statistics shows that 1261524-75-7 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-chlorobenzyl Alcohol.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; PIO, Barbara; TEUMELSAN, Nardos; PASTERNAK, Alexander; DEJESUS, Reynalda; WO2013/62892; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20605-01-0, Diethyl 2,2-bis(hydroxymethyl)malonate, 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, Product Details of 20605-01-0, blongs to alcohols-buliding-blocks compound. Product Details of 20605-01-0

General procedure: A solution of diethyl 2,2-bis(hydroxymethyl) malonate(12 mmol), 1 (10 mmol) and sulfonated carbon(1.0 g) were heated to reflux in a mixture of N,N-dimethylformamide(10 mL) and cyclohexane (6 mL)under stirring for 3 h. After cooling to room temperature,the solution was filtered and the solvent was removed in vacuo, the residue was dissolved in EtOAc (15 mL),washed with saturated brine (10 mL ¡Á 2) and water(10 mL¡Á2), dried over anhydrous Na2SO4. The solventwas filtered and concentrated to give 2a-2d as colorless oil.

The synthetic route of 20605-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Lin; Li, Zhong Yan; Zhang, Min; Yuan, Xian You; Zhu, Xiao Qing; Journal of Nanoscience and Nanotechnology; vol. 17; 3; (2017); p. 2201 – 2205;,
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