Month: February 2021

Related Products of 19500-02-8, These common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-methylaniline, 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.

Part A. Preparation of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. A solution of 44.4 g (344 mmol) of 3-methoxy-2-methylaniline and 75 g (344 mmol) of di-tert-butyl dicarbonate in 400 mL of THF was heated to maintain reflux for 4 hours. After concentrating at reduced pressure, the residue was taken up in ethyl acetate, washed with 1N citric acid, water and dried (MgSO4). After removing the solvent at reduced pressure, the residue was crystallized from hexane to give 64.5 g (84percent yield) of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline, mp, 56-57¡ã C. Analysis for C13H19NO3: Calculated: C, 65.80; H, 8.07; N, 5.90 Found: C, 63.32; H, 7.83; N, 5.56.

Statistics shows that 3-Methoxy-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 19500-02-8.

Reference:
Patent; Loh, Andrew; Macias, William Louis; Skerjanec, Simona; US2004/110825; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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 1836-62-0, Application In Synthesis of 2-(2-Methoxyphenoxy)ethylamine

EXAMPLE 1a [(cis)-4-(5-Fluoro-1H-indol-3-yl)-cyclohexyl]-[2-(2-methoxy -phenoxy)-ethyl]-amine A solution of 4-(5-fluoro-1H-indol-3-yl)-cyclohexanone (0.38 g,1.6 mmol), [2-(2-methoxy-phenoxy)-ethyl]-amine (0.27 g, 1.6 mmol), sodium triacetoxyborohydride (0.5 g, 2.2 mmol) and acetic acid (0.06 ml, 1.8 mmol) in 1,2-dichloroethane (8 ml) was allowed to stir at room temperature for 4 hours. The reaction was quenched with 1N sodium hydroxide (10 ml), extracted with methylene chloride (3 x 60 ml) and washed with brine (3 x 60 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. Chromatography (10% methanol-ethyl acetate) afforded 0.43 g(71%) of product as a white solid. The HCl salt was prepared in ethyl acetate: mp 186-188C.

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

Reference:
Patent; Wyeth; EP1068184; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 19500-02-8, name is 3-Methoxy-2-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 19500-02-8

[00194] lambda/-fe^Butyloxycarbonyl-2-methyl-3-methoxyaniline (3); [04-035-12]. A stirred solution of amine 2 (42.58 g, 0.31 mol) and di-te/t-butyl dicarbonate (65.48 g, 0.30 mol) in THF (3(T.sect.-m(L) was ‘heated to maintain reflux for 4 h. After cooling to RT, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc (500 mL). The resultant solution was washed with 0.5 M citric acid (2×100 mL), water (100 mL), saturated aqueous NaHCO3 (200 mL), brine (200 mL) and dried over MgSO4. After filtration and removal of the solvent from the filtrate, the residue (red oil, 73.6 g) was dissolved in hexanes (500 mL) and filtered through a pad of Silica Gel (for TLC). The filtrate was evaporated under reduced pressure to provide lambda/-Boc aniline 3 as a yellow solid. Yield: 68.1 g (96percent).

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; ILYPSA, INC.; WO2007/56275; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 78531-29-0, name is 1,3-Dimethoxypropan-2-amine, 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 78531-29-0, Recommanded Product: 1,3-Dimethoxypropan-2-amine

To a dry (0876) 200 round-bottomed flask was added di(2-pyridyl) thionocarbonate (5.34 g, 23.00 mmol) in DCM (73.0 ml). 2-Amino-l,3-dimethoxypropane (commericially available from Combi-Blocks Inc., 2.61 g, 21.90 mmol) in DCM (15 mL) was then added dropwise via an addition funnel over 5 min at RT with stirring. The reaction mixture was stirred at RT for 3.5 h. The reaction mixture was then concentrated in vacuo. The product was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% EtOAc in heptane, to provide the title compound Example 124.1 (3.28 g, 20.34 mmol, 93 % yield) as colorless oil. NMR (400MHz, CDC13) delta 3.95 (quin, J=5.49 Hz, 1 H) 3.50 – 3.60 (m, 4 H) 3.41 (s, 6 H). LCMS (pos.) m/z: 162.2 (M+H)+.

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, 1,3-Dimethoxypropan-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
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Synthetic Route of 109-85-3, The chemical industry reduces the impact on the environment during synthesis 109-85-3, name is 2-Methoxyethylamine, I believe this compound will play a more active role in future production and life.

To a colorless solution of methyl 3-fluoro-4-nitrobenzoate (50 g, 250 mmol) in THF (400 ml_) was added triethylamine (40.7 g, 402 mmol, 55.8 ml_) followed by addition of 2- methoxyethanamine (30.2 g, 402 mmol) in THF (100 ml_), drop-wise, at room temperature. The resultant yellow solution was stirred at 55 C for 18 hours. The solution was cooled to room temperature and concentrated under reduced pressure to remove THF. The resultant yellow solid was dissolved in EtOAc (800 ml_) and washed with saturated aqueous ammonium chloride solution (250 ml_). The aqueous phase was separated and extracted with EtOAc (200 ml_). The combined organic layers were washed with saturated aqueous sodium chloride solution (3 x 250 ml_), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield C49 (60.2 g, 94%) as a yellow solid. 1H NMR (CDCb) d 8.23 (d, 1 H), 8.17 (br s, 1 H), 7.58 (d, 1 H), 7.25 (dd, 1 H), 3.95 (s, 3H), 3.69 – 3.73 (m, 2H), 3.56 (m, 2H), 3.45 (s, 3H); LCMS m/z 255.4 [M+H]+.

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, 2-Methoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; ASPNES, Gary Erik; BAGLEY, Scott W.; CONN, Edward L.; CURTO, John M.; EDMONDS, David James; FLANAGAN, Mark E.; FUTATSUGI, Kentaro; GRIFFITH, David A.; HUARD, Kim; LIMBERAKIS, Chris; MATHIOWETZ, Alan M.; PIOTROWSKI, David W.; RUGGERI, Roger B.; (149 pag.)WO2019/239371; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 910251-11-5, 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 910251-11-5 as follows.

A 100-mL round-bottom flask charged with compound 1-2 (100 mg, 0.26 mmol, 1.00 equiv), p and potassium methoxylmethyltrifluoroborate (77.9 mg, 0.51 mmol, 2.00 equiv) in dioxane (30 mL) and water (3 mL). Then Pd(pddf)Cl2 (50 mg) and Cs2C03 (250 mg, 0.76 mmol, 3.00 equiv) were added and the resulting mixture was degassed three times with nitrogen and stirred overnight at 85C. The resulting mixture was diluted with 30 mL of water and was extracted with 3 x 50 mL of ethyl acetate. Organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by preparative HPLC to furnish 8.2 mg (9%) of 6-(methoxymethyl)-N-((lr,4r)-4- morpholinocyclohexyl)quina-zolin-4-amine, 1-32 as a white solid. LCMS (ES, m/z): 357.2 [M+H]+; 1H NMR (300 MHz, CD3OD) delta 8.43 (s, 1H), 8.19 (s, 1H), 7.77 (dd, 1H), 7.69 (d, 1H), 4.62 (s, 2H), 4.26-4.19 (m, 1H), 3.74 (t, 4H), 3.45 (s, 3H), 2.66 (t, 4H), 2.39 (d, 1H), 2.39 (d, 2H), 2.34 (d, 2H), 1.62-1.42 (m, 4H).

According to the analysis of related databases, 910251-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; SHELLEY, Mee; MASSE, Craig E.; HARRIMAN, Geraldine C.; WO2015/164374; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 36865-41-5, name is 1-Bromo-3-methoxypropane, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 36865-41-5

To a suspension of 4-chloro-3-hydroxy-5-nitrobenzamide (1.00 g, 4.62 mmol) in DMF (1991) (15 mL) was added l-bromo-3-methoxypropane (1.06 g, 6.93 mmol) and K2CO3 (1.91 mg, 13.9 mmol). The reaction mixture was stirred at 60 C in a sealed tube. After 3 hr, the reaction was cooled to RT and poured into water. The resulting light yellow precipitate was collected by filtration and washed with diethyl ether to provide the title compound (1.1 g, 3.8 mmol, 83 % yield). LCMS (LCMS Method D): Rt = 0.84 min, [M+H]+ = 289.0

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 36865-41-5.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHARNLEY, Adam Kenneth; DARCY, Michael G.; DODSON, Jason W.; DONG, Xiaoyang; HUGHES, Terry V.; KANG, Jianxing; LEISTER, Lara Kathryn; LIAN, Yiqian; LI, Yue; MEHLMANN, John F.; NEVINS, Neysa; RAMANJULU, Joshi M.; ROMANO, Joseph J.; WANG, Gren Z.; YE, Guosen; ZHANG, Daohua; (451 pag.)WO2017/175147; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 1535-73-5, These common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, 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: An aqueous solution of cesium carbonate (130 mg, 0.4 mmol) in water (300 ul) was dispensed into each well containing a pre-mixed solution of 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (58.8 mg, 0.2mmol), respective aniline (0.26 mmol), xantphos (13.9 mg, 0.024mmol) and palladium (II) acetate (3.6 mg, 0.016 mmol) in DMA (1.25 ml). The resultant plate was placed on a pre-heated SOPHAS base plate set at 150 oC and shaken for 1 hour. The plate was cooled to room temperature and MP-TMT resin (90 mg) added to each well prior to shaking overnight at room temperature. The following day each well was transferred to a 48 well filter plate, washing through with an extra aliquot of DMA (200 ul) before a final centrifuge. The crude filtrates were then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5mu silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford required N2-(4-methoxyphenyl)-N4-[aryl]pyridine-2,4-diamine (23-42%)

Statistics shows that 3-Trifluoromethoxyaniline is playing an increasingly important role. we look forward to future research findings about 1535-73-5.

Reference:
Article; Burton, Rebecca J.; Crowther, Mandy L.; Fazakerley, Neal M.; Fillery, Shaun M.; Hayter, Barry M.; Kettle, Jason G.; McMillan, Caroline A.; Perkins, Paula; Robins, Peter; Smith, Peter M.; Williams, Emma J.; Wrigley, Gail L.; Tetrahedron Letters; vol. 54; 50; (2013); p. 6900 – 6904;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (2-Bromo-5-methoxyphenyl)methanamine

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 ¡Á 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

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:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 112970-44-2,Some common heterocyclic compound, 112970-44-2, name is 2-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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 2-bromo-3-aminoanisole 2b4 (750mg, 3.7mmol, 1eq) was added imidate2g2 (0.73g, 3.7mmol, 1eq) in ethanol (7 ml) under a N2 atmosphere. The mixture wasstirred at R.T. for 24 hrs at which point the reaction was concentrated and purifieddirectly on a silica gel column (eluent: EtOAc/Hexanes (1:9)) to afford adduct 2o1(1.12g, 88%) as a pale yellow oil. MS: 344 (M + H)+ and 346 (MH + 2)+.

The synthetic route of 112970-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem