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Application of 4415-82-1, 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. 4415-82-1, name is Cyclobutylmethanol. A new synthetic method of this compound is introduced below.

To a mixture of 1.05 g (26.25 mmol; 60% purity) of sodium hydride in 15 ml of DMF were added 1.33 g (15.44 mmol) of cyclobutylmethanol and the mixture was stirred at RT for 1 h. Subsequently, a mixture of 1.0 g (7.72 mmol) of 3-chloropyrazin-2-amine in 10 ml DMF was added thereto and the reaction mixture was heated to 100 C. After 20 h, water was added to the mixture, which was extracted repeatedly with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated by evaporation. The residue obtained was purified by means of silica gel chromatography (eluent: cyclohexane/ethyl acetate gradient). 1.25 g of the title compound were obtained (89% of theory; 98% purity). (1270) LC-MS (Method 2): Rt=0.80 min (1271) MS (ESpos): m/z=180 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4415-82-1, Cyclobutylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; FOLLMANN, Markus; HARTUNG, Ingo; BUCHGRABER, Philipp; JAUTELAT, Rolf; LINDNER, Niels; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; Dietz, Lisa; LI, Volkhart Min-Jian; (85 pag.)US2016/176880; (2016); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 112-27-6, name is 2,2′-(Ethane-1,2-diylbis(oxy))diethanol, the common compound, a new synthetic route is introduced below. COA of Formula: C6H14O4

Briefly, p-toluenesulfonyl chloride (7.50 g, 40.0 mmol) was added to a solution of triethylene glycol (60.0 g, 40.0 mmol) in pyridine (6.5 mL) and dichloromethane (400 mL) and under nitrogen. After stirring for 18 hr at room temperature, the solvent was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with aq. NaCl solution (3*200 mL). The aq. extract was back extracted with ethyl acetate (2*100 mL), and the combined ethyl acetate phases were dried over MgSO4. After filtering and evaporating to dryness the product was purified on a silica column to yield a clear oil (9.30 g, 75%). 1H NMR (300 MHz, CDCl3, TMS): delta 7.82 (d, 3JHH=8.1 Hz, 2H), 7.36 (d, 3JHH=8.1 Hz, 2H), 7.19 (t, 3JHH=3.6 Hz, 2H), 3.59-3.78 (m, 10H), 2.47 (s, 3H). 13C NMR (75 MHz, CDCl3, TMS): delta 144.86, 132.93, 129.82, 127.96, 72.48, 70.77, 70.34, 69.13, 68.70, 61.74, 21.62. IR (NaCl): v=3421, 2886, 1594, 1358, 1169, 664 cm31 1.

The synthetic route of 112-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Holmes, Brian T.; Snow, Arthur W.; US2009/187037; (2009); A1;,
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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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