Tag: M.W=100-200

Application of 623-04-1, 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. 623-04-1, name is (4-Aminophenyl)methanol, molecular formula is C7H9NO, 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 p-amino-benzylalcohol (1 g, 8.12 mmol, 1 eq) in 80 mL of anhydrous THF were added DIEA (1.4 mL, 8.12 mmol, 1 eq) and BoC2O (1.9 mL, 8.12 mmol, 1 eq). The mixture was heated to reflux overnight, then cooled down and evaporated under vacuum. The residue was dissolved in EtOAc. The organic layer was washed with a 0.1 N HCl solution, dried over MgSO4, filtered and evaporated under vacuum. The crude product was purified by column chromatography on silica gel (Hex-EtOAc, 1:1, v/v) to give 1.85 g of product (quantitative yield): 1H NMR delta 0.1.49 (9H, s), 2.17 (IH, s), 4.53 (2H5 s), 6.83 (IH, s), 7.19 (2H, d, J = 8.5 Hz), 7.28 (2H, d, J = 8.2 Hz); 13 C NMR delta 28.28, 64.54, 80.37, 118.49, 127.59, 135.31, 137.46, 152.72.

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 623-04-1, (4-Aminophenyl)methanol.

Reference:
Patent; ENZON PHARMACEUTICALS, INC.; WO2008/34124; (2008); A2;,
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Adding a certain compound to certain chemical reactions, such as: 4845-50-5, 1,4-Dioxane-2,3-diol, 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, Quality Control of 1,4-Dioxane-2,3-diol, blongs to alcohols-buliding-blocks compound. Quality Control of 1,4-Dioxane-2,3-diol

To a solution of the corresponding compound 39G (0.9 mmol) in ethanol/water (30 mL/4 mL) was added l,4-dioxane-2,3-diol (130 mg, 1.08 mmol) and the resulting suspension was stirred at 30C overnight. The solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic layer was separated and washed with water and brine, dried over Na2S04 and concentrated, and then purified by a standard method to give title product 39H.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4845-50-5, 1,4-Dioxane-2,3-diol, and friends who are interested can also refer to it.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; POPOVICI-MULLER, Janeta; ZAHLER, Robert; YE, Zhixiong; WO2014/139144; (2014); A1;,
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Related Products of 30379-58-9 ,Some common heterocyclic compound, 30379-58-9, molecular formula is C9H10O3, 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 lithium 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin- l-yl)ethyl)methylsulfonamido)benzoate (theoretical 0.869 mmol) and EDC (349 mg, 1.821 mmol) in dry DCM (3 ml), benzyl 2-hydroxyacetate (151 mg, 0.910 mmol) and DMAP (1 1 1 mg, 0.910 mmol) were added at RT. The final mixture was stirred for 2 days, then the solvent was evaporated, the residue was portioned between water and EtOAc, the organic layer was washed with NaHC03 sat. sol. and brine, dried over Na2S04 and evaporated. The crude was purified by flash chromatography on silica gel (eluent: DCM/MeOH/32%NH4OH 95/5/0.5) to give 2-(benzyloxy)-2- oxoethyl 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-l-yl)ethyl)- methylsulfonamido)benzoate as a colorless oil (370 mg, 0.661 mmol, 76% yield over 2 steps, MS/ESI+ 560.1 [MH] +).

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. 30379-58-9, Benzyl 2-hydroxyacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; ESPOSITO, Oriana; PERETTO, Ilaria; WO2013/45280; (2013); A1;,
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Reference of 1450754-41-2 ,Some common heterocyclic compound, 1450754-41-2, molecular formula is C7H10N2O, 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.

4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenyl)picolinic acid, an intermediate with a monocarboxylic acid(0.063g, 0.145mmol)Dissolved in 3mL anhydrous tetrahydrofuran solution,Add EDC¡¤HCl (0.04 g, 0.218 mmol),HOBT (0.024 g, 0.174 mmol) was stirred well at 0 C, then DIPEA (0.094 g, .725 mmol) was added dropwise and stirred.1h,Add inPhotoaffinity group dipyridiniumAlkynyl chainConnector(0.02g, 0.145mmol),Stir at room temperature for 24 h,After the reaction is completed, the solvent is removed under reduced pressure, and an appropriate amount of ethyl acetate is added thereto, followed by washing with water and washing with saturated sodium hydrogen carbonate, and then sat.Washed with brine, combined with EtOAc (EtOAc m.The target compound was obtained, and weighed 0.03 g, yield 41.66%. Obtaining a general formula based on the VEGFR-2 inhibitor B14 photoaffinity probe

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. 1450754-41-2, 2-(3-But-3-ynyl-3H-diazirin-3-yl)-ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Lu Wen; Wang Sicen; Pan Xiaoyan; He Langchong; Sun Ying; Wang Jin; Song Jie; (10 pag.)CN109503553; (2019); A;,
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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 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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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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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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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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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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