Author: Jessica.F

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 109-85-3 as follows. SDS of cas: 109-85-3

A) Chloro(N-(2-methoxyethyl))acetamide, (1) In a three-necked 2L round bottom flask fitted with two 500mL addition funnels, containing 56.4g (39.8mL, 0.50mole) chloroacetyl chloride in 400mL dichloromethane and 20g (0.50mole) sodium hydroxide in 400mL water, respectively, and a water-cooled condenser, was placed 35.7g (41.3mL, 0.48mole) 2-methoxyethylamine, 100mL water, 100mL dichloro-methane. The reaction vessel was cooled to 0 C. by a salt-ice bath. The organic and aqueous solutions were allowed to add slowly, -0.25mL per minute, to the reaction mixture. During the addition the pH of the water phase of the reaction was monitored and the rate of addition of the alkali solution adjusted so as to maintain pH=12. When the addition was complete, the mixture was allowed to warm to room temperature and stir overnight. The organic layer was removed by siphon and dried with magnesium sulfate for four hours. The mixture was filtered through #4 filter paper on a large Buchner funnel and the sulfate washed with 2*100mL fresh dichloromethane. The combined filtrates were then placed in 2L round bottomed flask and the mixture distilled at torr. Fractions collected from 55 C. to 60 C. were combined and analyzed by NMR. Yield 31.lg (43% based on starting 2-methoxyethylamine). TLC (silica on glass, 2% methanol in dichloromethane) R67 =0.40. 1 H(delta, CDCl3) 3.28(s,3H), 3.40{m,4H}, 3.97{s,2H}, 6.92{br, IH}. 13 C{1 H}{delta, CDCl2 }39.27, 42.32, 58.60, 70.54, 166.22.

According to the analysis of related databases, 109-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mallinckrodt Medical, Inc.; US5138040; (1992); A;,
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Reference of 148583-65-7, These common heterocyclic compound, 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, 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.

EXAMPLE 9 1-(4-Fluoro-2-methylethoxyphenyl)piperazine (XXI) A crude solution of XX (8.35 g, 47.9 mmol), bis-(2-choroethyl)amine hydrochloride (12.83 g, 71.9 mmol) and triethylamine (10.00 mL, 71.7 mmol) in chlorobenzene (70 mL) was heated at reflux for 25 h. The dark brown reaction mixture was then partitioned between 3N NaOH and methylene chloride. The organic layer was separated, dried (MgSO4), filtered and concentrated to yield 15.9 g of a brown oil.

The synthetic route of 148583-65-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McNeilab, Inc.; US5569659; (1996); A;,
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Related Products of 109-85-3, These common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, 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: To a solution of nitrogen-containing nucleophile (1 eq.) and cesium carbonate (3.0 eq.) in N,N-dimethylformamide (2 mL/mmol) was added 2-haloheterocycle (1.1 eq.). Thereaction was heated to 100 C. and stirred at this temperature for 2 hours. Thereaction was then cooled to room temperature and acidified to pH=1 with 10%aqueous HCl solution if product contains a carboxylic acid, or diluted withwater if neutral. The solution was extracted with twice with dichloromethane.The organic layers were combined, dried with sodium sulfate and concentratedunder vacuum. The crude material was either used directly in subsequentreactions or purified by flash chromatography.

The synthetic route of 109-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
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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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-2-methoxynaphthalene

In a glove box, 1.0 mmol of 1-bromo-2-methoxynaphthalene, 2.0 mmol of aryl boronic acid, Pd2 (dba) 3, phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen , And the temperature was raised to 80 C, and the reaction was carried out for a period of time. The results are shown in Table 2 below.The amount of Pd2 (dba) 3 and the phosphine ligand is divided into two kinds: (1) 0.25 mol% Pd2 (dba) 3, 0.5 mol% phosphine ligand, or (2) 0.5 mol% Pd2 (dba) mol% phosphine ligand, depending on the amount of ligand used in Table 2.

According to the analysis of related databases, 3401-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Yu Sifan; Zhou Xiantai; (23 pag.)CN106995461; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, belongs to ethers-buliding-blocks compound, 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 31576-51-9, Computed Properties of C5H13NO2

A mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (100 mg, 0.2570 mmol) , 2- (2-methoxyethoxy) ethan-1-amine (37 mg, 0.3085 mmol) , HATU (146 mg, 0.3856 mmol) , DIPEA (99 mg, 0.7712 mmol) in DMF (3 mL) was stirred at rt for 3 hours. The reaction mixture was poured into H 2O (10 mL) and extracted with EtOAc (15 mL x 3) . The combined organic layer was washed with brine, dried over Na 2SO 4, concentrated and purified by column chromatography (DCM/MeOH=40: 110: 1) to give the target product (85 mg, 67.48%) . 1HNMR (400 MHz, DMSO-d6) delta 8.24 (s, 1H) , 7.98 (s, 2H) , 7.95 (s, 1H) , 7.56 (t, J = 5.6 Hz, 1H) , 7.34 -7.22 (m, 4H) , 7.15 (dd, J = 7.7, 1.5 Hz, 2H) , 6.74 (dd, J = 3.3, 1.8 Hz, 1H) , 3.46 -3.37 (m, 4H) , 3.29 (dd, J = 5.6, 3.0 Hz, 3H) , 3.22 (dd, J = 13.2, 6.0 Hz, 1H) , 3.13 (s, 3H) , 2.28 (s, 3H) . MS: M/e 491 (M+1) +.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
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Application of 2393-23-9, These common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, 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.

A mixture of l-[4-(methyloxy)phenyl]methanamine (40 g) and 4- (methyloxy)benzaldehyde (40.5 g) in methanol (220 mL) was heated to reflux for 3 hours. After cooling to 0 C, NaBH4 (14.34 g) was added portionwise within 30 min and the resulting mixture was stirred at room temperature overnight. Solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc for 3 times. The combined organic layers were washed with water and brine, then dried over anhydrous Na2SC>4. After filtration, solvent was removed in vacuo to afford bis {[4-(methyloxy)phenyl]methyl} amine (75.9 g) as a colorless oil. MS(ES+) m/z 258 (MH+).

Statistics shows that 4-Methoxybenzylamine is playing an increasingly important role. we look forward to future research findings about 2393-23-9.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; XIANG, Jia-Ning; WO2012/27965; (2012); A1;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 366-99-4

General procedure: To a solution of compound 12 (bakuchiol-o-triflate) (1 mmol) in toluene (10 mL M), amine (3.0 mmol), Cs2CO3 (4.0 mmol), ligand (±) BINAP (0.6 mol) and Pd(OAc)2 (0.2 mol) were added under an inert atmosphere. The reaction mixture was degassed at RT and refluxed (120 °C) for 24 hr. Then, the reaction mixture was brought to RT, diluted with EtOAc and filtered through celite. To the reaction mixture, brine (20 mL) was added and extracted with EtOAc (2 × 10 mL). The combined organic layerwas dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the product after silicagel chromatography purification (Hex/EtOAc, 9.5:0.5).

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 366-99-4.

Reference:
Article; Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 75 – 80;,
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Application of 7252-83-7, 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 7252-83-7 as follows.

Step 1: Methyl 2-bromo-3-cyclohexyl-l-(2.2-dimethoxyethyl)-lH-indole-6-carboxylate; To a stirred solution of methyl 2-bromo-3-cyclohexyl-lH-indole-6-carboxylate (prepared as described in published International patent application WO2004/087714) (0.2 M, 1 eq.) in DMF at RT was added NaH (60 % dispersion in mineral oil, 1.75 eq). After Ih, KI (8 mol %) and bromoacetaldehyde dimethyl acetal (2.5 eq) were added and the reaction heated at 80 0C for 17 h. After cooling to RT, the reaction was quenched by addition of aqueous HCl (IN) and extracted into EtOAc (x3). The combined organics were washed with HCl (IN), H2O and brine before being dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (Biotage, 5-10 % EtOAc/PE gradient) gave the title compound as a white solid (79 %); MS (ES+) m/z 446 (M+H)+, 448 (M+H)+.

According to the analysis of related databases, 7252-83-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); A2;,
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29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 1-Bromo-3-methoxy-5-methylbenzene

A. Cu(l)l (0.05 g, 0.25 mmol) and Nal (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 mi Anhydrous dioxane (5 mL), N,N-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and 1-bromo-3-methoxy-5-methylbenzene (Compound No. 24, 1.0 g, 5 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110C in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2CI2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (Compound No. 25, 1.05 g, 87% yield) as a pale yellow oil.

The synthetic route of 29578-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQUINOX PHARMACEUTICALS INC.; MACKENZIE, Lyoyd, F.; MACRURY, Thomas, B.; HARWIG, Curtis; BOGUCKI, David; RAYMOND, Jeffery, R.; PETTIGREW, Jeremy, D.; KHLEBNIKOV, Vladimir; SHAN, Rudong; WO2014/110036; (2014); A1;,
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Application of 1462-37-9, 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Under an argon atmosphere,methyl 2-(4-hydroxyphenyl)acetate (3.51 g, 21.14 mmol) and caesium carbonate (13.78 g, 42.28 mmol)were suspended in dimethylformamide (130 mL), the mixture was stirred at ambient temperaturefor 2 h. Benzyl-2-bromoethylether (5.00 g, 23.25 mmol) was added and it was stirred at ambienttemperature for further 12 h. Water (250 mL) and ethyl acetate (250 mL) were added and the resultingphases separated. The organic phase was dried over sodium sulfate and concentrated in vacuum.Purification by chromatography on silica gel (gradient: 0?100percent ethyl acetate in cyclohexane) affordedthe title compound 8a as a white solid (5.30 g, 84percent yield): 1H-NMR (DMSO-d6): delta = 7.38?7.26 (m, 5H),7.19?7.15 (m, 2H), 6.92?6.88 (m, 2H), 4.55 (s, 2H), 4.13?4.10 (m, 2H), 3.78?3.74 (m, 2H), 3.60 (s, 3H), 3.59(s, 2H) ppm. 13C-NMR (DMSO-d6): delta = 172.33, 157.88, 138.78, 130.83, 128.70, 127.99, 127.89, 126.83,114.83, 72.55, 68.71, 67.53, 52.06, 39.72 ppm. MS (m/z): 301 [M + H]+.

The chemical industry reduces the impact on the environment during synthesis ((2-Bromoethoxy)methyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
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