Month: January 2021

Reference of 36449-75-9, These common heterocyclic compound, 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, 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: General synthetic procedure for the final products.The appropriately substituted 4-phenethylpiperidine (6)(0.5 mmol) was dissolved in acetonitrile (5 mL) and K2CO3(0.75 mmol) and the appropriate phenethyl bromide (7) (0.5 mmol) added. The reaction mixture was refluxedfor 8 h.After completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambient temperature and filtered through a Celite pad. The filtrate was concentrated under vacuum to obtain the desired crude product. The crude product was further purified by column chromatography (silica gel: 3-5% methanol in dichloromethane) to afford the corresponding 1,4-diphenethylpiperidine (8a-8y) in good yield (75-80 %), which was then converted to hydrochloride salt by treatment with 2M HCl in diethyl ether.Compounds12a-12dwere synthesized using the same procedure as above, except that an appropriately substituted 4-benzylpiperidine (11) was utilized in place of compound6.

The synthetic route of 36449-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nickell, Justin R.; Culver, John P.; Janganati, Venumadhav; Zheng, Guangrong; Dwoskin, Linda P.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 2997 – 3000;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H13NO2

To a solution of 5-fluoro-2-nitrobenzoic acid (6.6g, 35.66 mmol) in dichloromethane (100 mL) were added DIPEA (9.22 g, 71.3 mmol), HOBt (6.0 g, 39.2 mmol) and EDCI (10.2 g, 53.5 mmol). After about 15 mm stirring, to the reaction mixture was added a solution of 2,4-dimethoxybenzyl amine (5.96 g, 35.66 mmol) in dichloromethane (50 mL) dropwise under nitrogen atmosphere. The resulting mixturewas stirred under nitrogen atmosphere at room temperature for 16 h. The reaction mixture was washed successively with iN HC1 (100 mL), sat. NaHCO3 (100 mL) and brine (100 mL). The organic phase was then dried over MgSO4. Filtration and solvent removal in vacuo afforded a yellowish solid, wt: 9.3g (78%). MS: [M+1] = 335.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 20781-20-8.

Reference:
Patent; MEKONNEN, Belew; BUTERA, John, A.; HUANG, Jianxing; (400 pag.)WO2016/205739; (2016); A1;,
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Application of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-amino-1-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. This mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt=1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/249190; (2010); A1;,
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Application of 13101-88-7, 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 13101-88-7 as follows.

1.- 2,5-dimethyl-2-(6-methoxynaphthalen-2-yldiazenyl)furan-3(2H)-one To a suspension of 2-amino-6-methoxynaphthalene (2.6 g, 15 mmol) in H2O (40 ml), HCl conc. was added (8 ml), it was cooled in an ice bath and a NaNO2 solution (1.19 g, 17.3 mmol) in H2O (18 ml) was added dropwise shaking the mixture at 0?C during 30 minutes. The previous solution was diluted in H2O (80 ml), 2,5-dimethylfuran-2,3-dihydrofuran-3-one (1.94 g, 17.3 mmol) was added and was left shaking during 2 hrs at room temperature resulting in a yellow precipitate. It was filtered, washed with water and dried. It was thereby obtained 2,5-dimethyl-2-(6-methoxynaphthalen-2-yldiazenyl)furan-3-one (4.22 g, 95 %) in a solid crude form of an ocre-yellow color that was used directly in the following synthesis step. 1H-NMR (300 MHz, CDCl3) delta ppm: 8.35 (s, 1H), 7.85 (d, J=8,8Hz, 1H), 7.75-7.7 (m, 2H), 7.2 (m, 2H), 5.55 (s, 1H), 3.95 (s, 3H), 2.45 (s, 3H), 1.75 (s, 3H).

According to the analysis of related databases, 13101-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios Del. Dr. Esteve, S.A.; EP2113501; (2009); A1;,
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Synthetic Route of 6298-96-0,Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

STEP 1 : A solution of (S)-I -(4-methoxyphenyl)ethanamine (3.10 g, 20.5 mmol) in dichloromethane (30 ml) was cooled to -78 C and a solution of boron tribromide (3.88 ml, 41 mmol) in dichloromethane (15 ml) was added dropwise. The reaction mixture was stirred at -78 C for two hours and then at room temperature for 2 h. The solution was then cooled to 0 C and water (15 ml) was added followed by saturated aqueous sodium carbonate to pH 8. The mixture was partially concentrated by rotary evaporation, tetrahydrofuran (50 ml) was then added followed by di-tert- butyl dicarbonate (4.47 g, 20.5 mmol) and the reaction mixture was stirred at room temperature overnight. The water layer was extracted with ethyl acetate (2x 150 ml) and the combined organic layers were washed with brine, dried over sodium sulfate then filtered and concentrated. The residue was purified by silica gel column chromatography using hexanes: ethyl acetate 4:1 to 3:1 as eluent to afford 1,1- dimethylethyl [(l S)-l-(4-hydroxyphenyl)ethyl]carbamate (2.90 g, 60 % yield). 1H NMR (400 MHz, CDCl3): 7.10 (br s, 2H), 6.73 (d, 2H), 6.07 (br s, IH), 4.91 -4.51 (m, 2H), 1.56-1.25 (m, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Methoxyphenyl)ethylamine, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
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These common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, 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. Safety of 1-Bromo-2-(trifluoromethoxy)benzene

2.0 g of 1-bromo-2-(trifluoro-methoxy)benzene (8.3 mmol) were dissolved in 30 ml of dichloromethane. At 0-50C, 1.06 g of chlorosulfonic acid (9.13 mmol), dis? solved in 3 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature. Additional 5.5 equivalents of chloro- sulfonic in dichloromethane were added to drive the reaction to completion.Standard work-up was followed and silica gel chromatography with n-heptane- dichloromethane (6:4) as eluent gave 2.19 g of the title compound.1H-NMR (CDCl3, 400 MHz): delta [ppm] 8.3 (d, 1H), 8.05 (dd, 1H), 7.5 (dd, 1H).

The synthetic route of 1-Bromo-2-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2006/40179; (2006); A1;,
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Application of 6298-96-0,Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

A mixture of 5-ethoxy-4-chlorothieno[2,3-d]pyrimidine (163 mg, 0.76 mmol) and (S)-1-(4-methoxyphenyl)ethylamine (120 mg, 0.79 mmol) and triethylamine (159 muL, 1.14 mmol) in DMF (2.0 mL) was allowed to react for 5 hours at 50 C. The reaction mixture was filtered through a cotton plug and purified by High Pressure Liquid Chromatography (HPLC) (Gilson system; Phenomenex column: Luna 5mu C18(2), 150¡Á21.20 mm, 5mu micro) with a water/acetonitrile gradient. Appropriate fractions were pooled to provide 125 mg of pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Methoxyphenyl)ethylamine, its application will become more common.

Reference:
Patent; Brewster, William Kirkland; Klittich, Carla Jean Rasmussen; Balko, Terry William; Breaux, Nneka Tuere; Erickson, William Randal; Hunter, James Edward; Lowe, Christian Thomas; Ricks, Michael John; Siddall, Thomas Lyman; Yerkes, Carla Nanette; Zhu, Yuanming; US2006/89370; (2006); A1;,
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Synthetic Route of 702-24-9, 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. 702-24-9 name is 4-Methoxy-N-methylbenzylamine, This 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.

General procedure: A secondary amine (0.34 mol), sodium methoxide (0.35 mol), diethyl ether (600 mL), and methanol (90 mL) were placed into a 1 L three-neck flask equipped with a stirrer, a condenser with a liquid valve, and a gas inlet. A flow of NO was passed at ~20 ¡ãC with vigorous stirring for 10 ?12 h at a rate allowing to maintainan excessive gas pressure within 13 ? 20 Torr. A dense precipitate formed was filtered, washed with diethyl ether, dried first on the filter, then in vacuo using an oil pump to obtain the corresponding sodium salts.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-N-methylbenzylamine, and friends who are interested can also refer to it.

Reference:
Article; Smirnov; Gordeev; Nikitin; Pokhvisneva; Ternikova; Luk?yanov; Russian Chemical Bulletin; vol. 64; 11; (2015); p. 2712 – 2717; Izv. Akad. Nauk, Ser. Khim.; 11; (2015); p. 2712 – 2717,6;,
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Application of 38336-04-8, 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. 38336-04-8 name is 2-(Benzyloxy)-1-ethanamine, This 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.

General procedure: Ethyl 2-(4-chloro-3-nitrophenyl)-2-methylpropanoate (3a)(16.15 g, 0.0594 mol), 4 (27.77 g, 0.149 mol), K2CO3 (28.69 g,0.208 mol), KI (0.99 g, 5.94 mmol), TBAB (1.91 g, 5.94 mmol) and150 mL DMSO were added into a round-bottomed flask. The mixturewas heated to 120 C for 24 h then cooling to room temperature.The reaction mixture was diluted with saturated NH4Claqueous solution (250 mL) and extracted with CH2Cl2 (450 mL).The combined organic layer was washed with brine (300 mL), driedover anhydrous sodium sulfate, filtered, and concentrated in vacuo.The residue was purified by silica gel column chromatography (PE:EtOAc = 4:1) to give compound 5a (15.82 g) as yellow oil in 69%yields.

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

Reference:
Article; Chen, Dongxing; Shi, Jinyu; Liu, Jing; Zhang, Xueying; Deng, Xiaoying; Yang, Yanyan; Cui, Shuang; Zhu, Qihua; Gong, Guoqing; Xu, Yungen; Bioorganic and Medicinal Chemistry; vol. 25; 2; (2017); p. 458 – 470;,
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These common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, 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. category: ethers-buliding-blocks

Step A: Preparation of (Z)-3-(dimethylamino)-2-methoxyacrylaldehyde: The reaction was carried out in a 3-neck flask (500 mL) equipped with an internal thermometer. PCl5 (64.4 g, 294 mmol) was added in small portions (~5 g) to a cold (0 C.) solution of 1,1,2-trimethoxyethane (36 g, 294 mmol) while keeping the internal temperature below 30 C. The mixture was heated to 60 C. for 75 minutes and then placed in an ice bath. DMF (66 mL, 852 mmol) was added via a dropping funnel while maintaining the internal temperature below a temperature of 10 C. The mixture was stirred at room temperature for 40 hours, and MeOH (100 mL) was added dropwise via a dropping funnel while keeping the internal temperature below 10 C. The solution was transferred to an addition funnel and was added dropwise to a 30% solution of sodium methoxide (403 mL, 2.17 mol) in MeOH while maintaining the internal temperature below 20 C. The mixture was heated at reflux for 4 hours and then concentrated. The residue was taken up in water (500 mL) and extracted with dichloromethane (500 mL*3). The combined organics were dried, filtered and concentrated to give the desired product (19 g, 25%). MS (APCI-pos) M+1=130.0.

The synthetic route of 1,1,2-Trimethoxyethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); A1;,
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