Month: May 2021

Related Products of 4342-43-2,Some common heterocyclic compound, 4342-43-2, name is 2-Methoxycyclohexanamine, molecular formula is C7H15NO, 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 64 To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10-20 C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatograpy (Wakogel C-200, eluding solvent, benzene_chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. Elementary analysis for C13 H23 N5 O2 S: Calcd. (%): C,52.50; H,7.79; N,23.55 Found (%): C,52.56; H,7.71; N,23.63

The synthetic route of 4342-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Company, Limited; US4540703; (1985); A;,
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Application of 41566-77-2, A common heterocyclic compound, 41566-77-2, name is 5-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride, molecular formula is C10H14ClNO, 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 the solution of 5-methoxy-indan-1-ylamine hydrochloride (92 mg, 0.46 mmol) and (3- cyclopropyl-1 ,4-dimethyl-1 H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid (buildingblock A7, 120 mg, 0.46 mmol) in DMF (6 ml) were added DIPEA (0.24 ml, 1.38 mmol) and HATU (210 mg, 0.55 mmol) and the reaction was stirred at rt for 30 min. The mixture was diluted with EtOAc, washed with aqueous bicarbonate solution and brine, dried over sodium sulfate, and the solvents were evaporated under reduced pressure. Purification by preparative HPLC (Gilson GX-281 , Waters Sunfire C18, 5muetaeta, 30 x 100 mm with guard column 19 x 10 mm, solvent A: water with 0.1% TFA, solvent B: acetonitrile, gradient 40-60% B in 15 min, flow reate 50 ml/min) gave the title compound as colorless solid (140 mg, 75%). [1 H-NMR (DMSO-de, 600 MHz) delta 8.40 (d, 1 H), 7.02 (d, 1 H), 6.81 (s, 1 H), 6.68 (d, 1 H), 6.48 (s, 1 H), 5.26 (dd, 1 H), 4.80 (s, 2H), 3.76 (s, 3H), 3.71 (s, 3H), 2.91-2.88 (m, 1 H), 2.78-2.73 (m, 1 H), 2.66 (s, 3H), 2.38-2.33 (m, 1 H), 2.28-2.24 (m, 1 H), 1.89-1.82 (m, 1 H), 0.92-0.85 (m, 4H); LCMS RtH = 3.095 min; [M+H]+ = 407.2]

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NOVARTIS AG; BADIGER, Sangamesch; BEHNKE, Dirk; BETSCHART, Claudia; CHAUDHARI, Vinod; CHEBROLU, Murali; COSTESTA, Simona; HINTERMANN, Samuel; MEYER, Arndt; PANDIT, Chetan; WO2011/76744; (2011); 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. 866633-25-2, name is 2-Bromo-4-fluoro-1-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H3BrF4O

Preparation 18 r2-(Trifluoromethoxy)-5-fluorophenyllboronic acid A solution of isopropylmagnesium bromide (2M solution in tetrahydrofuran) (83 ml, 0.166 mol) was added drop-wise to a stirred solution of 2-(trifluoromethoxy)-5-fluoro- 1-bromobenzene (Preparation 17, 27.6 g, 0.107 mol) in anhydrous tetrahydrofuran (125 ml) at -1 O0C under an atmosphere of nitrogen. The resulting mixture was stirred at room temperature for 2 hours. Triisopropyl borate (26.1 g, 0.139 mol) was then added drop-wise at -100C and the resulting mixture was stirred at room temperature for 16 hours. Hydrochloric acid (1 N aqueous solution) (100 ml) was added drop-wise at O0C and the mixture stirred at room temperature for 30 minutes. Ethyl acetate (150 ml) was added and the layers were separated, the aqueous layer was further extracted with ethyl acetate (2 x 150 ml). The organic extracts were combined and concentrated in vacuo. The residue was dissolved in potassium hydroxide (10% aqueous solution) (50 ml) and extracted with diethyl ether (2 x 150 ml). The separated aqueous layer was acidified to pH~4 by addition of hydrochloric acid (1 N aqueous solution) (100 ml) and extracted with ethyl acetate (3 x 150 ml). The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give an off white solid. Purification by preparative HPLC gave the title compound as an off white solid (5.82 g, 24%).1HNMR (de-DMSO): 7.23-7.32 (m, 3H), 7.53-7.55 (m, 1 H), 8.36 (br s, 1 H).MS m/z 223 [MH]-

According to the analysis of related databases, 866633-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2008/135830; (2008); A1;,
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Related Products of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, 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.

General procedure: A corresponding primary amine (1.1 equiv.) and an excess of 37% formalinaldehyde free of paraformaldehyde (1.0 mL, 13.5 mmol) were added to a suspension of Guareschi imide triethylammonium salt 1a-c (0.8-0.9 mmol) in EtOH (6-12 mL). The mixture was refluxed for 3-5 min with stirring and allowed to stand for48 h at 20 C (precipitation of the corresponding “bispidinate”5a-m is possible). The mixture was acidified with 10% aqueousHCl to pH 3-4, after 1 day a precipitate formed was collected by filtration, washed with cold EtOH and diethyl ether, and, if necessary, recrystallized from the acetone-EtOH solvent system

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

Reference:
Article; Chigorina; Frolov; Dotsenko; Goloveshkin; Bushmarinov; Krivokolysko; Russian Chemical Bulletin; vol. 65; 9; (2016); p. 2260 – 2269; Izv. Akad. Nauk, Ser. Khim.; 9; (2016); p. 2260 – 2269,10;,
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Electric Literature of 4132-48-3, 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. 4132-48-3, name is 4-Isopropylanisole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 4 To each of two-separate 22-L three-necked, round-bottomed reaction flasks equally equipped with thermometer, reflux condenser and mechanical stirrer, there were charged 1.3 Kg (7.4 moles) of 4-isopropylanisole (the product of Example 2) and 12.0 L of trifluoroacetic acid at ambient temperatures (ca. 20 C.) with constant agitation being maintained throughout the course of the entire addition step. This was then followed by the slow addition of 1.0 Kg (7.4 moles) of hexamethylenetetramine in small portions over a 50-minute period to the two well-stirred reaction mixtures now contained in each of the two-separate reaction flasks. The resulting reaction mixture in each flask then exothermed from 24 C. to 38 C. in each instance and was thereafter externally heated up to the reflux temperature of the reaction mixture at 81 C. The stirred and heated reaction mixture was next refluxed at this point for a period of 14 hours. Upon completion of this step, the trifluoroacetic acid solvent was removed from each of the two spent reaction mixtures via concentration under reduced pressure and each resulting residual oil was thereafter partitioned between 4 L of water and 4 L of hexanes. The pH of the two-phase system now contained in each flask was subsequently re-adjusted from a pH value of 0.5 to a value of pH 9.0 by adding thereto separate-3.8 L and 4.2 L portions of 6N aqueous sodium hydroxide solution, respectively. The basified two-phase systems were then allowed to settle and separate, and the two-separated aqueous layers were thereafter saved and subsequently washed with a fresh 2 L-portion of hexanes. The organic layers were next combined and subsequently backwashed with 3 L of water, followed by treatment with 200 g of activated charcoal and 400 g of anhydrous magnesium sulfate as drying agent. After removal of the latter two substances by means of suction filtration through celite, the resulting clear organic filtrate was subsequently concentrated in vacuo to give 2.0 Kg (72%) of crude aldehyde final product in the form of a dark residual oil. The latter material (1.8 Kg) was then purified by means of distillation in vacuo to ultimately afford 880 g (44%) of pure 2-methoxy-5-isopropylbenzaldehyde. The pure product was characterized by means of nuclear magnetic resonance (NMR) data. NMR Data: 1 H NMR(CD3 OD) delta1.05(d, 6H), 2.74(m, 1H), 3.75(s, 3H), 6.95(d, 1H), 7.35(dd, 1H), 7.35(dd, 1H), 7.5 1H, 10.23(s, 1H).

The chemical industry reduces the impact on the environment during synthesis 4-Isopropylanisole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US5294744; (1994); A;,
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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. 35202-55-2, name is (3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

1.5 mL of ethyl chloroformate are poured into a suspension of 3.4 g of the compound obtained in Step 1 in 4.5 mL of triethylamine and 50 mL of dichloromethane and left overnight, whilst stiffing at ambient temperature; washing with water and with 1N hydrochloric acid is then carried out. Drying is carried out and the solvent is evaporated off to dryness. 3.2 g of an oil corresponding to the expected product are obtained. [0046] Yield=80%

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 35202-55-2.

Reference:
Patent; LES LABORATOIRES SERVIER; CARRANZA, Maria Del Pilar; GARCIA ARANDA, Maria Isabel; GONZALEZ, Jose Lorenzo; SANCHEZ, Frederic; US2014/163220; (2014); A1;,
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Related Products of 202865-58-5,Some common heterocyclic compound, 202865-58-5, name is 1-Bromo-4,5-difluoro-2-methoxybenzene, molecular formula is C7H5BrF2O, 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.

1-bromo-4,5-difluoro-2-Methoxy – benzene (1.0g, 4.5mml), 4- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (1.09g, 4.93mmol), PdCl2 (dppf) (328mg, 0.448mmol) and sodium carbonate (1.51g, 11.2mmol) of 1,4-dioxane and a mixed solution of water (40mL, v / v = 4/1) in addition, at 100 the mixture was stirred for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried with anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel chromatography (hexane / ethyl acetate), to give the title compound. Yield: 1.13g (3.56mmol) Yield: 79%

The synthetic route of 202865-58-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO COMPANY INCORPORATED; MIYANAGA, WATARU; NAKAGAWA, TADAKIYO; DOHI, MIZUKI; MATSUMOTO, KAYO; TOKUMASU, MUNETAKA; TAKESHITA, SEN; (58 pag.)JP2016/13983; (2016); A;,
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Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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. name: 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene

4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene (87.0 g, 349.27 mmol) was dissolved in THF (700 mL) and cooled to -78 C. n-Butyl lithium (185.42 mL of a 2.5 M soln in hexanes, 461.04 mmol) was rapidly added and immediately followed by addition of DMF (40.40 mL, 523.91 mmol). Reaction was stirred in the cold for 30 min then allowed to warm to rt and stirred for 1 h. The reaction solution was diluted with H2O (500 mL) and extracted with Et2O (3*500 mL). The combined organic extracts were washed with brine (3*200 mL), dried (Na2SO4), filtered, concentrated and chromatographed (eluted with 10% EtOAc in hexanes) to provide 45.90 g of 4-(dimethoxymethyl)-3-fluorobenzaldehyde as a clear oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 439814-87-6, its application will become more common.

Reference:
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
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Application of 92028-21-2,Some common heterocyclic compound, 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, molecular formula is C13H14ClNO, 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 compound JJ hydrochloride (73.7 g, 114 mmol) and 4-methoxy-3-phenylaniline hydrochloride (32.4 g, 137 mmol), toluene (380 mL) was added with mild agitation for 5 minutes, followed by sodium tert-butoxide (49.3 g, 513 mmol) in portions over 1 minute, and finally 2,2′-bis(diphenylphosphino)-11beta-binaphthyl (10.65 g, 17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (5.22 g, 5.7 mmol). The resulting mixture was stirred and heated to 85-89 C. (internal) for 2.5 hours. The solution was cooled to room temperature, water (400 mL) was added and the mixture was stirred for 5 minutes, filtered through Celite (80 g), and partitioned with toluene (100 mL). The organic layer was collected and concentrated under reduced pressure in a 40 C. bath to give N-{2-[4-(3-phenyl-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-tert-butyldimethylsilyl-2-(8-benzyloxy-2(1H)-quinolinon-5-yl)ethylamine (NN) as a dark viscous oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, its application will become more common.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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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. 53903-49-4, name is 4-Methoxy-2-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Formula: C8H8F3NO

2-Amino-5-methoxy-benzotrifluoride (10.46 mmol), K3PO4 (15.7 mmol), Xphos (1.05 mmol) and Pd4(dba)3 (0.314 mmol) were added under nitrogen to a solution of 4-bromo-2-fluoro-benzonitrile (10.46 mmol) in 50 mL toluene and the mixture was stirred for 20 hours at a bath temperature of 110 C. Then the mixture was filtered through a glass fibre filter, then the filtrate was extracted with 150 mL water. The organic phase was dried on sodium sulphate and evaporated down. In this way the product was obtained in a yield of 87% of theory. C15H10F4N2O (310.2) Mass spectrum (ESI): [M+H]+=311 [M-H]-=309 Thin layer chromatograph (silica gel; petroleum ether/ethyl acetate 7:3): Rf=0.48

The synthetic route of 53903-49-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/208823; (2012); A1;,
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