Month: August 2021

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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9BrO2

Example 26; Compound No.7; (S)-2-amino-N-(5-(3-methoxy-5-(piperidin-4-yloxy)phenyl)pent-4-ynyl)pent-4-ynamide; STEP A: 3-Bromo-5-methoxyphenol; 1-Bromo-3,5-dimethoxy-benzene (0.217 g, 0.001 mol) and KCN (0.20 g, 0.003 mol) were taken up into DMSO (10 mL) and the resulting mixture stirred at 120 C. for six hours, then at 150 C. overnight. The mixture was maintained at this temperature, with stirring for another day. The reaction was then quenched with water and the resulting mixture extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, then dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was purified on normal phase chromatography (Heptane/EtOAc) to yield 3-bromo-5-methoxyphenol. MH+ 203, 205

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Parker, Michael H.; Hlasta, Dennis J.; Huang, Yifang; Reitz, Allen B.; Lawson, Edward C.; Schubert, Carsten; Strobel, Eric; Tounge, Brett A.; White, Kimberly; Winters, Michael P.; Ghosh, Shyamali; US2011/105562; (2011); A1;,
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Application of 24332-20-5,Some common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, molecular formula is C5H12O3, 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 3: (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione A round bottom flask was charged with 2-methoxyacetaldehyde dimethyl acetal (2076 mul, 2076 mumol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (299 mg, 2076 mumol). The flask was fitted with a reflux condenser and the mixture was heated at 100 C. for 2 h under nitrogen. 5,6-Dimethoxypyridin-3-amine (320 mg, 2076 mumol) was added, and within a minute a solid had precipitated out of solution. The heterogeneous mixture was heated at 100 C. for 10 min. The mixture was cooled to RT and the solids were filtered and washed with hexanes. (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was isolated as a yellow/orange solid. MS [M+H]=309.

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

Reference:
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
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Reference of 1112210-82-8,Some common heterocyclic compound, 1112210-82-8, name is 1,3-Dibromo-5-isopropoxybenzene, molecular formula is C9H10Br2O, 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.

Synthesis of intermediate I-b: 3-bromo-5-isopropoxy-benzaldehydeTo a solution of I-a (4.630 g, 15.75 mmol) in dry Et20 (60 mL) under inert atmosphere was added dropwise at -78C a solution of n-butyl lithium in dry Et20 (6.3 mL, 15.75 mmol). The reaction mixture was stirred at -78C for 0.5 h. Then, dry DMF (1.35 mL) was added dropwise at -78C and the temperature was allowed to reach -40C over 1.5 h. A solution of HC1 (3N) was added and the crude product was extracted with Et20 (2 times), the organic layer was washed with water, then with a saturated solution of NaCl, dried over MgS04 and concentrated to give I-b as yellow oil in 82% yield. 1H RMN (300 MHz, CDC13) delta 9.89 (s, 1H), 7.54 (m, 1H), 7.29 (m, 2H), 4.60 (dt, J = 12.1, 6.0 Hz, 1H), 1.36 (t, J= 6.0 Hz, 6H).

The synthetic route of 1112210-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AB SCIENCE; BENJAHAD, Abdellah; MOUSSY, Alain; CHEVENIER, Emmanuel; PICOUL, Willy; LERMET, Anne; PEZ, Didier; MARTIN, Jason; SANDRINELLI, Franck; WO2013/14170; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2688-84-8, name is 2-Phenoxyaniline, 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 2688-84-8, category: ethers-buliding-blocks

According to Scheme 34, intermediate 5-a was synthesized:2-Penoxyaniline (25.0, 0.135 mol), 30 ml of hydrochloric acid and 150 ml of water were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 C and stirred for 1 hour.At the same temperature, 75 ml of an aqueous solution of sodium nitride (11.2 g, 0.162 mol) was added dropwise, followed by stirring for 1 hour.75 ml of an aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise noting the temperature of the reaction solution not to exceed 5 degrees. After stirring for 5 hours at room temperature, the reaction was completed, washed with sodium thiosulfate aqueous solution and extracted with ethyl acetate and water.The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain Patent; SFC Ltd.; Cha Sun-uk; Jeong Gyeong-seok; Song Ju-man; Lee Yu-rim; Park Sang-u; Kim Hui-dae; Park Seok-bae; (65 pag.)KR2019/111856; (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. 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;,
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. 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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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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