Tag: M.W=100-200

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 102-52-3 as follows. SDS of cas: 102-52-3

ethyl 2-aminopyrazolo[l ,5-a]pyrimidine-3-carboxylateA mixture of ethyl 3,5-diamino-l H-pyrazole-4-carboxylate (1.0 g, 5.9 mmol), 1,1,3,3- tetramethoxypropane (2.9 mL, 18 mmol), triethylamine (2 mL, 10 mmol), and DMF (15 mL) was heated at 100 0C for 14 hrs, then a further 2 mL of 1,1,3,3-tetramethoxypropane was added. After adding the additional 1,1,3,3-tetramethoxypropane, a significant by-product was noted and heating was stopped immediately. The reaction was cooled to room temperature and the DMF was removed in vacuo. The residue was partitioned between DCM and water, then the organic layer was concentrated and the residue purified by silica chromatography, eluting with 95:5 DCM: 2M methanolic ammonia solution to afford 420 mg (35%) of ethyl 2-aminopyrazolo[l,5- a]pyrimidine-3-carboxylate. 1H NMR (500 MHz, CDCl3) delta 8.57 (dd, J = 4.3, 1.6, IH), 8.43 (dd, J = 6.7, 1.6, IH), 6.84 (dd, J = 6.7, 4.4, IH), 5.52 (s, 2H), 4.48 (q, J= 7.1, 2H), 1.45 (t, J= 7.1, 3H).

According to the analysis of related databases, 102-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; GIBBONS, Paul; HANAN, Emily; LIU, Wendy; LYSSIKATOS, Joseph P.; MAGNUSON, Steven R.; MENDONCA, Rohan; PASTOR, Richard; RAWSON, Thomas E.; SIU, Michael; ZAK, Mark E.; ZHOU, Aihe; ZHU, Bing-Yan; WO2011/3065; (2011); A2;,
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150-78-7, name is 1,4-Dimethoxybenzene, 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. HPLC of Formula: C8H10O2

Example 1 : Preparation of 2,5-dimethoxybromobenzene (1); [00101] In a one liter round-bottom flask, a solution of bromine (16.0 g, 100 mmol) in acetic acid (50 ml) was added dropwise to a solution of 1 ,4- dimethoxybenzene (13.8 g, 100 mmol) in chloroform and methanol (400 ml) at 00C. After stirring for 3 hours, 500 ml of saturated Na2CO3 solution was added. The organic layer was washed with water, brine and dried over sodium sulfate. After the solvent was removed on a rotary evaporator, the residue was distilled under reduced pressure to yield 15.8 g of 2,5- dimethoxybromobenzene (yield 73%) 1HNMR (CDCI3) 57.148 (s, 1 H), 6.859 EPO (s, 2 H), 3.869 (s, 3 H), 3.785 (s, 3 H).

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NATIONAL UNIVERSITY OF SINGAPORE; WO2006/93467; (2006); 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., name: 3-Fluoro-4-methoxyaniline

3-Fluoro-4-methoxyaniline (1, R1 = H, R2 = CH3, R3 = F) (95 g, 0.67 mol) was added to concentrated hydrochloric acid (250 mL), the suspension was stirred at ambient temperature for 18 hours, then it was cooled to 0 0C and a solution of sodium nitrite (53.7 g, 0.78 mol) in water (200 mL) was added dropwise at 0-5 0C. When the addition was complete, the resulting solution was stirred at 0 0C for 1 hour then it was added dropwise at 0-5 0C to a stirred solution of tin (II) chloride dihydrate (638.9 g, 2.83 mol) in concentrated hydrochloric acid (500 mL). The mixture was allowed to warm to ambient temperature then it was stored at 4 0C for 18 hours. The resulting precipitate was collected by filtration, washed with water (400 mL), and ether (1000 mL) and dried in vacuo. The solid hydrochloride salt was basifed by addition to 10percent aqueous sodium hydroxide solution (800 mL), the free base was extracted into ether (2 X 400 mL), and the combined extracts were dried (MgSO4) and the solvent removed in vacuo to give (3- fluoro-4-methoxyphenyl)hydrazine (2, R1 = H, R2 = CH3, R3 = F) (51.9 g, 50percent) as a yellow solid, mp 46-50 0C; 1HNMR (CDC13/25O MHz): 1.5 (s, IH, NH-NH2), 3.85 (s, 3H, OCH5), 5.0 (s, 2Eta, NH-NH2), 6.44 (m, 1Eta, phenyl 6-H), 6.60 (dd, 1Eta, phenyl 5-H), 6.79 (t, 1Eta, phenyl 2-H)-

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MICROBIA, INC.; WO2007/22501; (2007); A2;,
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Synthetic Route of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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 mixture of 3,4-dihydroxycinnamic acid (497mg, 2.76mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (794mg, 4.14mmol), 1-hydroxybenzotriazole (HOBt) (559mg, 4.14mmol), Et3N (0.58mL, 4.14mmol) in anhydrous DMF (10mL) was stirred under an atmosphere of argon for 10minat 26C. Propane-1,3-diamine (102mg, 1.38mmol) was added, and the mixture was stirred for 18hat 26C. The mixture was concentrated under reduced pressure to give a crude coupling product of the title compound (2). To facilitate isolation, the coupling product was treated with Ac2O (10mL) in pyridine (10mL) at 26C for 12h. The mixture was concentrated, and extracted with EtOAc and water for three times. The organic layers were combined and washed with water (10mL) and brine (10mL). The organic phase was dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (EtOAc elution) to afford the acetylation compound. To a solution of the acetylation compound in MeOH (10mL) was added K2CO3 (13mg, 0.13mmol). The mixture was stirred for 0.5hat 26C, and then acidified to pH 5 by addition of Dowex 50WX8-200 cationic exchange resin. The resin was then removed by filtration. The filtrate was concentrated, and purified by silica gel chromatography (EtOAc, then MeOH/CH2Cl2 1:4) to give pure compound 2 (146mg, 27% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Article; Tu, Ling-Hsien; Tseng, Ning-Hsuan; Tsai, Ya-Ru; Lin, Tien-Wei; Lo, Yi-Wei; Charng, Jien-Lin; Hsu, Hua-Ting; Chen, Yu-Sheng; Chen, Rong-Jie; Wu, Ying-Ta; Chan, Yi-Tsu; Chen, Chang-Shi; Fang, Jim-Min; Chen, Yun-Ru; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 393 – 404;,
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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. 1484-26-0, name is 3-Benzyloxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1484-26-0

3-Benzyloxyaniline (80 mg, 0.40 mmol) was dissolved in DCM and cooled to 0 °C. Bromoacetyl bromide (2 equiv, 70 lL) and Et3N (5 equiv, 280 lL) were added slowly and the mixture was stirred at 0 °C for 6 h. 2,5-Dimethoxybenzylamine (2.5 equiv, 151 lL)was added at 0 °C and the mixture was allowed to warm over 16 h of stirring. Boc2O (6 equiv, 524 mg) was added along with 2 addition equiv of Et3N and DMAP (0.2 equiv, 10 mg) and the mixture was stirred for 1 h at rt. The reaction mixture was diluted with satd NaHCO3 and extracted with DCM. The crude product was purified by pTLC with 30percent EtOAc in hexane to afford N-Boc-33 as a colorlessoil (49 mg, 24percent).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bremer, Paul T.; Hixon, Mark S.; Janda, Kim D.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3971 – 3981;,
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Reference of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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 2.05 g (14 mmol) of 3,3-diethoxypropan-1-amine 3 and 2.83 g (28 mmol) of triethylamine in 15 ml of benzene 14 mmol of N,N-di(alkyl, aryl)carbamoyl chloride was added dropwise at cooling (5-7 C). The reaction mixture was stirred under cooling for 2 hours. The precipitate was filtered off, the filtrate was evaporated in vacuum to give the target compound 4 as a yellow oil, which was used in subsequent reactions without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Article; Smolobochkin, Andrey V.; Gazizov, Almir S.; Burilov, Alexander R.; Pudovik, Michail A.; Synthetic Communications; vol. 48; 19; (2018); p. 2545 – 2552;,
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Reference of 20781-20-8, A common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

1-(2,4-Dimethoxyphenyl)methanamine (1.97 mL, 13.1 mmol) was added to a solution of 2-methyltetrahydro-4H-pyran-4-one (500 mg, 4.4 mmol) in methanol (10 mL). After stirring for 1 hour at room temperature, the reaction mixture was cooled to -78 C. and a solution of lithium borohydride (98%, 85 mg, 3.8 mmol) in tetrahydrofuran (1.5 mL) was added drop-wise. The reaction mixture was allowed to slowly warm to room temperature overnight, whereupon it was cooled to -20 C. and quenched via careful addition of saturated aqueous sodium bicarbonate solution. Ethyl acetate (25 mL) and sufficient water to solubilize the precipitate were added, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on silica gel [Gradient: 0% to 15% (10:1 methanol/concentrated ammonium hydroxide) in ethyl acetate] provided the product as a colorless oil. Yield: 936 mg, 3.53 mmol, 80%. 1H NMR (400 MHz, CDCl3) delta 7.13 (d, J=8.0 Hz, 1H), 6.46 (d, half of AB quartet, J=2.2 Hz, 1H), 6.44 (dd, half of ABX pattern, J=8.1, 2.3 Hz, 1H), 4.00 (ddd, J=11.6, 4.6, 1.6 Hz, 1H), 3.82 (s, 3H), 3.81 (s, 3H), 3.76 (s, 2H), 3.37-3.46 (m, 2H), 2.63-2.72 (m, 1H), 1.85-1.92 (m, 1H), 1.78-1.85 (m, 1H), 1.37 (dddd, J=13, 12, 11, 4.6 Hz, 1H), 1.20 (d, J=6.2 Hz, 3H), 1.10 (ddd, J=12, 11, 11 Hz, 1H)

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Galatsis, Paul; Henderson, Jaclyn Louise; Kormos, Bethany Lyn; Kurumbail, Ravi G.; Reese, Matthew Richard; Stepan, Antonia Friederike; Verhoest, Patrick Robert; Wager, Travis T.; Pettersson, Martin Youngjin; Garnsey, Michelle Renee; (150 pag.)US2017/73343; (2017); A1;,
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Related Products of 366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of the amine (10.05mmol) in isopropanol (20ml) was added N,N-diisopropylethylamine (1.55g, 12mmol) and 2,4,5-trichloropyrimidine (1.84g, 10mmol). The reaction mixture was reflux for 2h followed by cooling to room temperature. Water (100ml) was added and the mixture was stirred for 30min. Then the mixture was filtrated. The solid was dried to provide the title compound 2a-2u.

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Hong; Li, Ridong; Ning, Xianling; Zhao, Xuyang; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 141 – 153;,
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These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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 4-Methoxy-N-methylbenzylamine

A mixture of 3 -( 5 -amino-2-chloro-4-fluorophenyl )-7 -chloro-1-methyl-1, 6-naphthyridin-2(1H)-one (2.5 g, 7.4 mmol) and 4-methoxy-N-methylbenzylamine (4 mL) washeated to 180°C under N2 for 3 h. After cooling, the reaction mixture was diluted with Et20.The precipitate was filtered, washed with water, and dried to give 7-((4-methoxybenzyl )(me thy l)amino )-3 -( 5 -amino-2-chloro-4-fluorophenyl )-1-methyl-1, 6-naphthyridin-2(1H)-one (3 g, 89percent yield). 1H NMR (400 MHz, DMSO-d6): 8 8.47 (s, 1 H),7.77 (s, 1 H) 7.22 (m, 2 H), 7.17 (d, J = 8.0 Hz, 2 H), 6.86 (d, J = 8.4 Hz, 2 H), 5.86 (d, J =9.6 Hz, 1 H), 6.30 (s, 1 H), 5.32 (s, 2 H) 4.87 (s, 1 H), 3.72 (s, 3 H), 3.52 (s, 3 H), 3.09 (s, 3H); MS (ESI) m/z: 453.2[M+H(

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

Reference:
Patent; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2013/184119; (2013); A1;,
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Application of 393-15-7, 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 393-15-7 as follows.

General procedure: 2-Bromoethyl amine (1 equiv.) and 4-Chlorphenylsulfonylchloride (1 equiv.) were dissolved in dry CH2Cl2under argon and triethyl amine (1.5 equiv) was added. The resultingreaction mixture was stirred at room temperature for 5 h. Then, waterand CH2Cl2 were added, followed by thorough extraction of theaqueous layer with CH2Cl2. The combined organic layer was driedover Na2SO4 and concentrated under reduced pressure. The residue waspurified via column chromatography (heptane/EtOAc, gradient 10:0 to1:1) to afford desired N-(2-bromoethyl)-4-chlorobenzene sulfonamideas intermediate which was dissolved in toluene (15 mL/mmol).Thereafter, a solution of KOH (3 equiv) in water (1 mL/mmol) wasadded. The resulting reaction mixture was stirred at room temperaturefor 90 min. After complete conversion, water and ethyl acetate wereadded, followed by thorough extraction of the aqueous layer withEtOAc. The combined organic layer was dried over Na2SO4 andconcentrated under reduced pressure. The residue was purified viacolumn chromatography (heptane/EtOAc, gradient) to afford desired 1-[(4-chlorophenyl)sulfonyl]aziridine as intermediate. 1-[(4-chlorophenyl)sulfonyl]aziridine (150 mg, 0.69 mmol), 4-fluoro-3-trifluoromethyl aniline (123 mg, 0.69 mmol) and SiO2 (100 mg,1.66 mmol) were then suspended in H2O (2 mL), and the resultingreaction mixture was treated with ultra sound for 90 min and wasstirred at room temperature for 20 h. Upon addition of water and ethylacetate the aqueous layer was extracted thoroughly with ethyl acetate.The combined organic layer was dried over Na2SO4 and concentratedunder reduced pressure. Purification of the remaining residue viacolumn chromatography (heptane/EtOAc, gradient) afforded N-(2-{[4-fluoro-3-(tri-fluormethyl)phenyl]amino}ethyl)-4-chlorobenzenesulfonamide

According to the analysis of related databases, 393-15-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Frackenpohl, Jens; Schneider, Linn; Decker, Luka J.B.; Dittgen, Jan; Fenkl, Franz; Fischer, Christian; Franke, Jana; Freigang, Joerg; Getachew, Rahel; Gonzalez Fernandez-Nino, Susana M.; Helmke, Hendrik; Hills, Martin J.; Hohmann, Sabine; Kleemann, Jochen; Kurowski, Karoline; Lange, Gudrun; Luemmen, Peter; Meyering, Nicole; Poree, Fabien; Schmutzler, Dirk; Wrede, Sebastian; Bioorganic and Medicinal Chemistry; vol. 27; 24; (2019);,
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