Ethers-buliding-blocks

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. 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H13NO

A mixture of phenyl 5-({trans-4-[(2-chloro-4,5-difluorophenyl)carbamoyl]cyclohexyl}carbamoyl)-1 H-im idazole-4-carboxylate (100 mg, 0.199 mmol,) and 2-methoxy-2-methylpropan-1 -amine (103 mg, 0.994 mmol, GAS No 89282-70-2) in tetrahydrofuran (5.0 ml) was stirred at 600 ove r night. For work-up, the reaction mixture was concentrated and the residue was first purified by flash chromatography (10 g Snap Gartridge, ethyl acetate/ethanol gradient, 0% -> 5% ethanol) followd by purification withpreparative HPLG (Method 9) to yield the title compound (46.0 mg, 45% yield).LG-MS (Method 3): R = 1.15 mm; MS (ESIpos) m/z = 512.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 13.38-13.09 (m, 1H), 11.25-1 0.90 (m, 1H), 9.67-9.53 (m, 1H), 8.52-8.25 (m, 0.5H), 8.21-7.95 (m, 0.5H), 7.87-7.75 (m, 3H), 3.92-3.59 (m, 1H),3.37 (d, 2H), 3.15 (5, 3H), 2.15-1.77 (m, 4H), 1.65-1.20 (m, 4H), 1.14 (5, 6H).

According to the analysis of related databases, 89282-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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 36805-97-7, HPLC of Formula: C11H25NO2

To a hot (800C) solution of 4-bromo-3-methyl benzoic acid (3.00 g, 13.95 mmol) in toluene (250 ml_), N,N-dimethylformamide di-terf-butyl acetal (11.35 g, 50.2 mmol) was added. The mixture was stirred at 800C for 8 h and at rt for 16 h before another portion of lambda/,lambda/-dimethylformamide di-terf-butyl acetal (5.67 g, 25.1 mmol) was added. Stirring was continued at 80C for 16 h. The mixture was cooled to rt, diluted with EA and washed with sat. aq. NaHCO3-solution followed by water. The org. layer was separated, dried over Na2SO4, filtered, evaporated and dried under high vacuum at 400C to give terf-butyl 4-bromo-3-methyl benzoate as a pale yellow oil (2.31 g). LC-MS: tR = 1.10 min; [M+1]+ = not detectable; 1H NMR (CDCI3): £ 1.61 (s, 9H), 2.46 (s, 3H), 7.59 (d, J = 8.3 Hz, 1 H), 7.66 (d, J = 8.3 Hz, 1 H), 7.86 (s, 1 H).

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; ACTELION PHARMACEUTICALS LTD; WO2009/109904; (2009); A1;,
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Electric Literature of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.

Magnesium (172.4 mg; made by Wako Pure Chemical Industries Co., Ltd.), dehydrated THF (5 mL), dibromoethane (20 muL; made by Tokyo Chemical Industry Co., Ltd.), and 1-(benzyloxy)-3-bromobenzene-THF solution [15 mL; solution prepared by dissolving 1-(benzyloxy)-3-bromobenzene (1.3146 g; made by Tokyo Chemical Industry Co., Ltd.) in dehydrated THF (15 mL)] were added and stirred for one hour by reflux in a nitrogen atmosphere. The reaction solution was cooled to – 78C and bubbled for 20 minutes by SO2 gas. The reaction solution was brought to room temperature, bubbled for 10 minutes with nitrogen gas, and filtered. The filtrate was concentrated, and the residue obtained was dissolved in CH2Cl2 (25 mL), then cooled to 0C. SO2Cl2 (0.6 mL; made by Wako Pure Chemical Industries Co., Ltd.) was added to this solution and stirred overnight while warming to room temperature. Water was added to the reaction solution. After filtering by Celite, the filtrate was washed with brine. The organic layer was dried by anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The title compound was obtained as a crude product (1.3811 g). This crude product was used in the next reaction without any particular purification.

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Kasei Pharma Corporation; EP2484668; (2012); 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. 21702-84-1, name is 2,4-Dibromo-1-methoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,4-Dibromo-1-methoxybenzene

General procedure: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

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; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
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Synthetic Route of 20781-20-8,Some common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

Step 42.3: N*6*-tert-butyl-2-chloro-N*8*-(2,4-dimethoxy-benzyl)-9-(tetrahydro-pyran-2-yl)- 9H-purine-6,8-diamine (Buchwald type amination, Method E) A solution of [8-Bromo-2-chloro-9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]-tert-butyl-amine (compound of Step 41.2, 77 mg, 0.2 mmol), 2,4-dimethoxybenzylamine (40 mg, 0.24 mmol), potassium phosphate tribasic (60 mg, 0.28 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (8 mg, 0.02 mmol), and Pd2(dba)3 (9 mg, 0.02 mmol) are stirred in dimethoxyethane (0.5 mL) under argon for 20 h at 100C. The reaction mixture is cooled to RT, diluted with ethyl acetate, washed with 10% sodium bicarbonate, and brine. The combined organic phases are dried over sodium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (CombiFlashNo. Companion RediSep column hexane/ethyl acetate gradient 20: 1 to 4: 1) to afford N*6*-tert-butyl-2-chloro-N*8*-(2,4- dimethoxy-benzyl)-9- (tetrahydro-pyran-2-yl)-9H-purine-6,8-diamine (55 mg, 58%), HPLC tR : 6.03, (M+H)+ = 475.1.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
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Reference of 2734-70-5, 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 2734-70-5 as follows.

To a mixture of Compound 4b (0.37 g, 3.9 mmol) and 2,6-dimethoxyaniline (0.5 g, 3 mmol) in toluene (5 mL), at 0° C., was added a 2M solution of trimethylaluminum in hexane (2 ml, 4 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and heated at 110° C. overnight. The reaction mixture was allowed to cool to RT and quenched with saturated aqueous Rochelle’s salt and EtOAc. The phases were separated, the aqueous phase was extracted with EtOAc. The organic phases were combined and washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0 to 30percent MeOH/0.5percent TEA in DCM to give Compound 4c (0.35 g, 44percent yield) as an orange oil. MS m/z=249.4 (M+H). 1H NMR (methanol-d4) delta 7.01 (t, J=8.3 Hz, 1H), 6.64 (d, J=8.3 Hz, 2H), 2.29-2.48 (m, 2H), 1.50-1.67 (m, 2H), 0.78-0.93 (m, 1H), 0.44 (s, 2H), 0.02-0.16 (m, 2H).

According to the analysis of related databases, 2734-70-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Pi, Zulan; Bilder, Donna M.; Brigance, Robert Paul; Finlay, Heather; Jiang, Wen; Johnson, James A.; Lawrence, R. Michael; Meng, Wei; Myers, Michael C.; Phillips, Monique; Tora, George O.; Zhang, Xiaojun; (59 pag.)US2017/275272; (2017); A1;,
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Related Products of 929-75-9, These common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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.

0.500 g of cinnamic acid, 0.295 g of 1,11-diamino-3,6,9-trioxadecane, 0.647 g of EDCI, 0.037 g of DMAP, 10 mL of anhydrous dichloromethane were sequentially added to the round bottom flask, and stirred at room temperature. After 12 h, 20 mL of dichloromethane was added, and the mixture was washed successively with brine (1×30 mL) and water (2×30 mL), dried over anhydrous sodium sulfate, filtered, evaporated to dryness Chloroform/methanol = 35:1; 50:4) gave 0.178 g of a pale yellow oily substance, yield 28% (see Figure 49 for the synthetic route and Figure 50 for the characterization)

Statistics shows that 1,11-Diamino-3,6,9-trioxaundecane is playing an increasingly important role. we look forward to future research findings about 929-75-9.

Reference:
Patent; Chinese Academy Of Medical Sciences Biomedical Engineering Institute; Liu Tianjun; Wang Jiawen; Li Guoliang; Hong Ge; Wang Wenzhi; (37 pag.)CN110229110; (2019); 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. 458-50-4, name is 4-Bromo-3-fluoroanisole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluoroanisole

A mixture of tert-butyl ((3S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1-(5-(2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamido)-1H-indol-4-yl)pyrrolidin-3-yl)carbamate (50 mg, 0.072 mmol), 1-bromo-2-fluoro-4-methoxybenzene (22.3 mg, 0.109 mmol), copper(I) iodide (2.1 mg, 10.9 mumol) and potassium phosphate, tribasic (32.3 mg, 0.152 mmol) was purged with N2 and treated with N,N-dimethylcyclohexane-1,2-diamine (6.2 mg, 0.043 mmol) in 0.5 mL toluene. The reaction mixture was further treated with 0.3 mL DMF and heated to 110 C. for 40 hrs. After cooling to r.t., the reaction mixture was diluted with water and EtOAc. The separated organic phase was washed with brine, dried over sodium sulfate and concentrated under vacuum. The crude product was dissolved in 1 mL THF and treated with 0.5 mL of TBAF solution (1.0 M in THF). The resulting mixture was stirred at r.t. for 1 hr, then diluted with water and EtOAc. The separated organic phase was washed with brine, dried over sodium sulfate and concentrated under vacuum. The crude was purified by flash chromatography (eluted with EtOAc) and the obtained product was then dissolved in 1 mL DCM and treated with 1 mL TFA. The resulting mixture was stirred at r.t. for 1 hr and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C32H31F2N6O4 (M+H)+: m/z=601.2; found 601.4.

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 458-50-4.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Nguyen, Minh; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Qinda; Yao, Wenqing; (72 pag.)US2019/315717; (2019); A1;,
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Electric Literature of 2674-34-2,Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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 solution of compound Q-9 (5.0 g, 16.77 mmol) in CH3CN (50 mL) was heated to 100 0C, followed by the addition of a solution of eerie ammonium nitrate (CAN, 14 g, 25.54 mmol) in water (75 mL) over a period of 30 min. The reaction mixture was then allowed to cool to room temperature and stirred for another 30 min. The resulting precipitate was filtered, washed with water (20 mL), and dried under high vacuum to furnish compound Q-10 (2.6 g, 58%) as a yellow solid. TLC Rf = 0.4 (petroleum ether – EtOAc, 9:1); MS (ES) mlz 266 (M – H)”.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; DJABALLAH, Hakim; ANTCZAK, Christophe; WO2010/129049; (2010); A1;,
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Application of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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 stirred solution of 5-chloro-2-ethylpyrazolo[1,5-a]pyridine-3-carboxylic acid or 2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (1.34mmol) in DMF (20mL) was added EDCI (0.39g, 2.01mmol), HOBt (91mg, 0.67mmol) and Et3N (0.68g, 6.7mmol) at room temperature. After 1h of stirring, 1a-8a (1.34mmol) was added and the reaction was heated to 80C for overnight. The mixture was cooled, and diluted with EA (50mL), washed with water and brine, dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography to afford the title compounds1-8.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Xiaoyun; Tang, Jian; Cui, Shengyang; Wan, Baojie; Franzblauc, Scott G.; Zhang, Tianyu; Zhang, Xiantao; Ding, Ke; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 41 – 48;,
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