Tag: M.W=100-200

Reference of 1758-46-9, These common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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 6] Compound D (150 mg, 483 mumol), 2-phenoxyethylamine (127 mul) and sodium hydrogencarbonate (400 mg) were added to DMSO (3 ml), and the mixture was stirred at 100°C for 27 hr. After stirring, the reaction mixture was added dropwise to cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and concentrated, and the residue was washed by suspending in ethyl acetate to give the object compound of 2-(2-phenoxyethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-(pyridin-3-yl)nicotinonitrile (82 mg). 1H-NMR (400MHz, DMSO-d6) delta (ppm): 12.06 (1H,br-s), 10.22 (1H,br-s), 8.72-8.69(2H,m), 7.98(1H,dd), 7.65(1H,dd), 7.29-7.23(2H,m), 6.96-6.90(3H,m),6.16(1H,br-s),4.23(2H,t),3.67(2H,t),2.22(3H,s). m/z=412 (M+H)

The synthetic route of 1758-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1876178; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)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 74654-07-2, Computed Properties of C7H17NO3

(iv) tert-Butyl (4-((2-((3-ethvnyl-5-((2-(2-(2-methoxyethoxy)ethoxy)ethyl)carbamoyl)- phenyl)amino)pyridin-4-yl)oxy)naphthalen-1-yl)carbamateHATU (500 mg, 1.315 mmol) was added to a stirred solution of the product from step (iii) above (500 mg, 1.009 mmol), 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (277 mg, 1.695 mmol) and triethylamine (250 pL, 1.796 mmol) in N,N-dimethylformamide (10 mL). The mixture was stirred at rt for 18 h. The mixture was diluted with EtOAc (50 mL) and washed with water (50 mL), 20% brine (3 x 50 mL) and saturated brine (50 mL). The organic phase was dried (MgSC ), filtered and concentrated under reduced pressure. The crude product was purified by chromatography on the Companion (40 g column, EtOAc) to afford the sub-title compound (580 mg) as a tan foam.LCMS m/z 641 (M+H)+(ES+); 639 (M-H)”(ES”)

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

Reference:
Patent; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew Colin Thor; THOM, Stephen Malcolm; BAKER, Thomas Matthew; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; RIGBY, Aaron; WO2015/92423; (2015); A1;,
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Application of 39538-68-6, These common heterocyclic compound, 39538-68-6, name is 2-Methoxy-4-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.

To a solution of cupric bromide (6.35 g; 28.4 mmol) in acetonitrille (25 ml_) was added tert- butyl nitrite (2.85 ml 24.06 mmol) and the mixture was heated at 65^ under a nitrogen atmosphere. A solution of 2-methoxy-4-methylaniline (3 g; 21 .87 mmol) in acetonitrile (25 ml_) was added carefully and the mixture was stirred for 20 min at 65 ‘O. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed (x 3) with an aqueous solution of ammonia 5%, water, a solution of ethylenediaminetetraacetic acid, water, brine and the mixture was concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2 – 50 %) in heptane furnished 2.32 g (53 %) of the title compound as a yellow oil.

Statistics shows that 2-Methoxy-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 39538-68-6.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; CHALTIN, Patrick; DEBYSER, Zeger; DE MAEYER, Marc; MARCHAND, Arnaud; MARCHAND, Damien; SMETS, Wim; VOET, Arnout; CHRIST, Frauke; WO2011/15641; (2011); 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. 22483-09-6, name is 2,2-Dimethoxyethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 2,2-Dimethoxyethanamine

Preparation 22 [0100] [0101] A solution of aminoacetaldehyde dimethyl acetal (25 mL, 229 mmol) in toluene (120 mL) is treated at 0 C. with a 4.85 M sodium hydroxide solution (70.8 mL, 343.5 mmol). The mixture is stirred at 0 C. for 10 minutes and benzyl chloroformate (33.8 mL, 229 mmol) is added keeping the internal temperature below 20 C. during the addition. The mixture is warmed to room temperature over 4 hours. The organic layer is separated, washed with brine, dried over sodium sulfate, and concentrated to dryness to give the title compound (54 g, 98%). ES/MS (m/e): 240 (M+H).

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; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
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These common heterocyclic compound, 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, 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. Formula: C5H13NO2

Preparation U N-[2-(2-Methoxyethoxy)ethyl]-1H-imidazole-1-carboxamide The title compound was prepared in 40% yield according to the procedure described in Preparation S above, using 2-(2-methoxyethoxy)ethylamine in place of 2-(4-morpholinyl)-1-ethanol.

The synthetic route of 2-(2-Methoxyethoxy)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bjorsne, Magnus; Ponten, Fritiof; Strandlund, Gert; Svensson, Peder; US2002/137766; (2002); 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6298-96-0

Example II (S)-4-(1-Amino-ethyl)-phenol hydrobromid To 11.0 g (72.7 mmol) (S)-1-(4-methoxy-phenyl)-ethylamine is added carefully 30 mL HBr (30% in HOAc). The mixture is stirred at 100 C. for 4 h. After cooling down to r.t., the solvent is removed in vacuo and the residue is dried in vacuo. The resulting product is used without further purification. C6H11NO*HBr (M=218.1 g/mol) ESI-MS: 121 [M+H-NH3]+Rt (HPLC): 0.50 min (method A)

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 6298-96-0.

Reference:
Patent; FLECK, Martin; NOSSE, Bernd; HEINE, Niklas; ROTH, Gerald Juergen; US2013/158004; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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 93919-56-3, name: (4-(Trifluoromethoxy)phenyl)methanamine

General procedure: To a solution of 4 (290mg, 1.02mmol) in DMF (1.5mL), CDI (198mg, 1.23mmol) was added under N2 protection. The resulting reaction was stirred 50C. After 2h, the mixture was cooled to room temperature, and the corresponding benzylamine (1.53mmol) was added. The resulting reaction was stirred 50C under N2 protection overnight. Then the mixture was cooled to room temperature, quenched with 1M hydrochloric acid, diluted with water (50mL), and extracted with CH2Cl2 (60mL×3). The combined organic layer were washed with saturated solution of NaCl (60mL×3), dried over MgSO4, concentrated and purified by flash chromatography eluting with 5-50% ethyl acetate in petroleum ether, to provide the desired products 5a-5d.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-(Trifluoromethoxy)phenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Liu, Siming; Jiang, Ying; Yan, Ruohong; Li, Zhonghuang; Wan, Shanhe; Zhang, Tingting; Wu, Xiaoyun; Hou, Ju; Zhu, Zhengguang; Tian, Yuanxin; Zhang, Jiajie; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 358 – 375;,
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Reference of 111-95-5,Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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 5 Synthesis of DTPA bis(di(2-methoxyethyl-amide)(3) 12.4 ml of bis(2-methoxyethyl)amine (0.084 mol), dissolved in 40 ml of anhydrous DMF, are added dropwise to 5_grams of DTPA anhydride (0.014 mol), dissolved in 80_ml of anhydrous DMF, under argon at 80 C. The reaction medium is kept stirred for 24 hours.After concentrating and addition of diethyl ether, the oily precipitate is separated from the solvents by settling.This residue is dissolved in the minimum amount of CHCl3 and reprecipitated from Et2O. After drying under vacuum, a hygroscopic foam (3) is obtained (6.43 g, yield of 74%), used without additional purification. 1H NMR (D2O+NaOD): 2.50 (t, 4H), 2.52 (t, 4H), 2.98 (s, 2H), 3.11 (s, 4H), 3.31 (s, 6H), 3.32 (s, 6H), 3.51 (s, 4H), 3.53-3.56 (m, 16H).13C NMR (D2O): 45.94, 47.03, 47.81, 49.75, 53.69, 56.29, 57.78, 67.16, 69.56, 69.69 (CH2); 58.63, 59.07 (OCH3); 166.9, 170.5, 175.7 (CO2H and CO). ES-MS: ES-: 622.1 ([M-H]-), ES+: 624.3 ([M+H]+), 646.2 ([M+Na]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Bis(2-methoxyethyl)amine, its application will become more common.

Reference:
Patent; Lemaire, Marc; Foos, Jacques; Guy, Alain; Chitry, Frederic; Pellet-Rostaing, Stephane; Vigneau, Olivier; US2004/81604; (2004); A1;,
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These common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)aniline, 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. Quality Control of 3-(Difluoromethoxy)aniline

A solution of 4-chloro-6-nitro-2- (pyrazin-2-yl) quinazoline (1.00 g, crude, 3.7 mmol, 1.0 equiv), 3- (difluoromethoxy) benzenamine 600 mg, 3.7 mmol, 1.0 eq) and Et 3 N (1.00 g, 10 mmol, 3.0 eq) was stirred at 75 C. for 18 h. After cooling, the volatiles were removed in vacuo and the residue was washed with H 2 O (100 mL × 2). The solid was dried in vacuo to give 1.40 g of N- (3- (difluoromethoxy) phenyl) -6-nitro-2- (pyrazin-2-yl) quinazolin-4-amine as a black solid 90.2% at the stage). LCMS m / z = 411.0 (M + 1) (Method A) (retention time = 1.61 min).

The synthetic route of 3-(Difluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL COMPANY LIMITED; SUZUKI, MASAKI; KONDO, KAZUMI; KURIMURA, MUNEAKI; VALLURU, KRISHNA REDDY; TAKAHASHI, AKIRA; KURODA, TAKESHI; TAKAHASHI, HARUKA; FUKUSHIMA, TAE; MIYAMURA, SHIN; GHOSH, INDRANATH; DOGRA, ABHISHEK; HARRIMAN, GERALDINE; ELDER, AMY; SHIMIZU, SATOSHI; HODGETTS, KEVIN J; NEWCOM, JASON S; (678 pag.)JP6121658; (2017); B2;,
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These common heterocyclic compound, 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene, 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. Application In Synthesis of 1,2,3-Trimethoxy-5-methylbenzene

Eine Loesung von 1047 g (3,973 mol) 5-Brom-2-methoxy-6-methylben- ZOESaeURECHLORID in 1715 g Chlorbenzol wurden mit 0,72 g (0,0044 mol) (Beispiele 1 bis 4und 7) bzw. 0,36 g (0,0022 mol) (Beispiel 5) bzw. 0,18 g (0,0011 mol) (Beipiel 6) wasserfreiem Eisen- (III) chlorid versetzt und zu einer Loesung von 868,7 g (4,768 mol) 3,4, 5-Trimethoxytoluol in 467,8 g Chlorbenzol bei der in der Tabelle angegebenen Reaktionstemperatur waehrend 4 h dosiert. An- schliessend wurde das Reaktionsgemisch 2 h bei Reaktionstemperatur nachgeruehrt. Zur Entfernung der entstandenen HC1 wurde waehrend der Dosier-und Nachruehrzeit ein konstanter Stickstoffstrom durch das Reaktionsgemisch geleitet (der jeweilige Volumenstrom kann der Tabelle entnommen werden). Anschliessend wurde das Chlorbenzol bei 80 mbar und Temperaturen von 80-105C abdestilliert. Reinheit und Ausbeute der rohen Produktschmelze wurden vor Kristallisation mittels quantitativer HPLC analysiert (Ergebnisse siehe Tabelle). Zur Kristallisation des 5-Bromo-2′, 6-dimethyl-2,4′, 5′, 6′-tetrame- thoxybenzophenons (I’) wurden 4900 g Methanol bei 50C vorgelegt und die 105C heisse Schmelze eingetragen. Die Kristallisation er- folgte durch Abkuehlung mittels einer Temperaturrampe bis AUF-5C. Die Titelverbindung wurde durch Zentrifugation isoliert, auf der Zentrifuge mit Methanol gewaschen und getrocknet.

The synthetic route of 1,2,3-Trimethoxy-5-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2004/54953; (2004); A1;,
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