Month: July 2021

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. 7664-66-6, name is 4-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H13NO

To a mixture of 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-iodoquinazoline-2,4-dion (200 mg, 0.4 mmol), palladium acetate (13.5 mg, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52.2 mg, 0.09 mmol), cesium carbonate (261 mg, 0.8 mmol) and dioxane mL) was added 4-isopropoxyaniline (0.071 ml, 0.48 mmol) under nitrogen atmosphere, and the resulting mixture was heated at reflux for 2 hours. The reaction mixture was poured into a mixture of water (1.00 mL) and 5% aqueous citric acid (10 mL), and the resulting mixture was extracted with ethyl acetate (100 mL). The extract was washed by water (100 mL), dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the residue was precipitated by hexane to give 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-(4-isopropoxyphenylamino)-quinazoline-2,4-dion (7.7 mg, Yield: 3.7%) as yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 1.28 (3H, t, J=7.2 Hz), 1.33 (6H, d, J=6.0 Hz), 4.24 (2H, q, J=7.2 Hz), 4.74 (1H, m), 4.88 (2H, s), 5.29 (2H, s), 5.61 (1H, s), 6.84 (2H, d, J=8.7 Hz), 6.91 (1H, d, J=9.0 Hz), 7.01 (2H, d, J=8.7 Hz), 7.11 (1H, dd, J=3.0, 9.0 Hz), 7.19 (2H, d, J=8.7 Hz), 7.30 (2H, d, J=8.7 Hz), 7.68 (1H, d, J=2.7 Hz).

According to the analysis of related databases, 7664-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIONOGI & CO., LTD.; Kai, Hiroyuki; Endoh, Takeshi; Jikihara, Sae; Horiguchi, Tohru; US9212130; (2015); B2;,
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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., HPLC of Formula: C7H8FNO

To cyanuric chloride (28.84 g, 156.0 mmol) dissolved in acetone (200 mL) stirring at approximately 0-5 C, was added a solution of 3-fluoro-p-anisidine (22.16 g, 156.0 mmol) in acetone (200 mL) followed by the addition of NaOH (63 mL, 2.5 N, 156.0 mmol). The reaction mixture was allowed to stir at approximately 0-5 C for about 2 hours. The reaction mixture was then poured over crushed ice and neutralized with 10percent HCI(aq) and 5percent NaOH(aq). The resulting solid was collected by vacuum filtration, washed with water and dried overnight under vacuum. Column chromatography (silica gel, 70: 30 hexane: ethyl acetate) yielded light yellow solid compound 124 (29.6 g, 66percent); mp 134 C ; HPLC: Inertsil ODS-3V C18,40 : 30: 30[KH2PO4(O. 01M, pH 3.2) :CH30H : CH3CN], 264nm, Rt 20.3 min, 97.7 percent purity.

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 366-99-4.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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Electric Literature of 16452-01-0,Some common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, molecular formula is C8H11NO, 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.

Reference Intermediate R2 4-methyl-3-(methyloxy)phenol [1376] 4-methyl-3-(methyloxy)aniline (Reference Intermediate R1, 1.86 g) in water (100 mL)/ H2SO4 (30 mL, 563 mmol) at 0 C. a solution of sodium nitrite (1.029 g, 14.91 mmol) in water (10 mL) was slowly added and the reaction mixture was stirred for 30 minutes at 0 C. The reaction mixture was slowly added to a solution of H2SO4 98% (20 mL) in Water (80 mL) pre-heated at 90 C. and stirred at this temperature for 1 h. After cooling the mixture was extracted with Et2O (2×200 mL), the organic layer was dried on sodium sulphate, filtered and evaporated to afford the title compound (1.86 g) as a red/brown oil. [1378] 1H-NMR (400 MHz, DMSO-d6) delta ppm: 9.14 (1H, br.s), 6.87 (1H, d), 6.35 (1H, d), 6.24 (1H, dd), 3.71 (3H, s), 2.01 (3H, s); UPLC_B: 0.63 min, 137 [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 3-Methoxy-4-methylaniline, its application will become more common.

Reference:
Patent; AUTIFONY THERAPEUTICS LIMITED; Alvaro, Giuseppe; Dambruoso, Paolo; Tommasi, Simona; Decor, Anne; Large, Charles; US2013/267510; (2013); A1;,
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Reference of 14227-17-9, A common heterocyclic compound, 14227-17-9, name is 2,4,6-Trimethoxyaniline, molecular formula is C9H13NO3, 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.

Method C A solution of Intermediate 7 (584 MG,-1. 63 MMOL) in DICHLOROMETHANE (10 mL) was added dropwise at 20C within 10 minutes to a stirred solution of dicyclohexylcarbodiimide (DCC; 370 mg, 1.79 mmol) and pyridine (265 mg, 3.35 MMOL) in dichloromethane (10 mL). The mixture was stirred at 20C for a further 24 hours, followed by addition of DMAP (4.0 mg, 33 PMOL) in one single portion. Subsequently, a solution of Intermediate 1 (358 mg, 1.95 MMOL ; freshly distilled by bulb-to-bulb distillation directly before use) in dichloromethane (5 mL) was added to the stirred mixture at 20C within 10 minutes, and stirring was continued for a further 3 days at 20C (formation of a precipitate). The mixture was then washed with water (2 x 25 mL), the organic layer was separated,. and the aqueous wash solutions were extracted with dichloromethane (2 x 20 mL) in the same order as they had been used for workup. The organic extracts were combined and dried over anhydrous sodium sulphate (remaining solids that did not dissolve in neither phase were filtered off along with the sodium sulphate), the solvent was removed under reduced pressure (rotary evaporator, 800 MBAR/40C), and the residue was dried in vacuo (10 mbar, 20C, 30 minutes) and then purified by column chromatography (column diameter, 3.5 cm; column length, 70 cm; SILICA GEL (15-40, UM, Merck 1.15111), 250 g; eluent, ethyl acetate/n-hexane 55: 45 (V/V)). The relevant fractions (TLC, ethyl acetate/n- hexane 55: 45 (V/V), RF = 0.42) were combined, the solvent was removed under reduced pressure (rotary evaporator; 350 to 150 mbar, 40C), and the residue was dried in vacuo (0.01 mbar, 20C, 1 hour) to give 454 mg of an oil which was dissolved in diethyl ether (8 mL). The resulting solution was then kept undisturbed at 4C for 2 days and AT-20C for a further 4 days (formation of a precipitate). The crystalline solid was isolated by decantation, washed with n- pentane (3 mL), and dried in vacuo (0.01 mbar, 20C, 4 hours) to give 5- [ (3, 5,5, 8, 8-pentamethyl-5, 8-disila-5, 6,7, 8-TETRAHYDRO-2-NAPHTHYL) METHYLL-N-(2, 4, 6- trimethoxyphenyl) furan-2-carboxamide in 37% yield as a colourless crystalline solid (318 mg, 607, UMOL) ; mp 139 C. ANAL. CALCD FOR C28H37NO5SI2 : C, 64. 21; H, 7.12 ; N, 2.67. Found: C, 64. 2; H, 7.1 ; N, 2.7.

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; AMEDIS PHARMACEUTICALS LTD.; WO2004/45625; (2004); A1;,
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Synthetic Route of 207226-31-1, These common heterocyclic compound, 207226-31-1, name is 1,3-Dibromo-5-(trifluoromethoxy)benzene, 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 1,3-dibromo-5-(trifluoromethoxy)benzene (25 g, 78.15 mmol, 1 eq) in i-Pr2O (50 mL) was added n-BuLi (2.5 M, 32 mL, 1.02 eq) at -78C for 0.5 h, then acetone (7.9 g, 136 mmol, 10 mL, 1.74 eq) was added. The mixture was stirred at 20C for 2 h. The reaction mixture was poured into 100 mL of aqueous NH4Cl and the resulting mixture was stirred for 15 min. The organic phase was separated, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give a residue. The residue was purified by flash silica gel chromatography (ISCO; 80 g SepaFlash Silica Flash Column, Eluent of 0~1% Ethylacetate/Petroleum ethergradient 50 mL/min). The title compound (8 g, 26.75 mmol, 34% yield) was obtained as a yellow liquid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.94 (s, 6 H), 5.90 (s, 1 H), 7.91 – 8.01 (m, 2 H), 8.19 – 8.25 (m, 1 H).

The synthetic route of 207226-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
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Reference of 102-52-3,Some common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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 amixtureof5.0g (19.6 mmol) ofL-tryptophan methylesterand50 mLof methanol,6.0 mL(23.6 mmol) of 1,1,3,3-tetramethoxypropane wasadded. The reaction mixture wasadjusted pH 1-2 withHCl(5N) and stirred at 45 Cfor 48h. The mixture was evaporatedto dryness in vacuo, the residue wasdissolved in a mixture ofwater(30mL) and ethyl acetate (30mL),and the aqueousphasewas extracted with ethyl acetate (30mL×3). The organic phase wascombined, washed successively with 10%Na2CO3andsaturatedNaCl,dried over anhydrousNa2SO4, filtered, andevaporatedto dryness in vacuo. The residue was purified by chromatographyonsilica gel (Chloroform: Methanol, 30:1) toobtain5.4 g of the title compound as pale yellow oilin 88.5% yield.ESI-MS (m/e) 319 [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 1,1,3,3-Tetramethoxypropane, its application will become more common.

Reference:
Article; Wu, Jianhui; Zhao, Ming; Wang, Yuji; Wang, Yaonan; Zhu, Haimei; Zhao, Shurui; Peng, Shiqi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 19; (2016); p. 4631 – 4636;,
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Related Products of 39021-83-5,Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, 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 magnetically stirred solution of 1 ,4-dimethoxy-2,3-dimethyl-benzene (13.90 g, 83.6 mmol) in carbon tetrachloride (300 mL) at room temperature was added N-bromo- succinimide (32.2 g, 176 mmol) in one portion, and the reaction mixture was heated up to 65C. Benzoyl peroxide (0.54 g, 2.23 mmol) was added at 65C, and the reaction mixture stirred for further 4 hours before cooling down to 55C. The reaction mixture was filtered, the solid washed with carbon tetrachloride, and the combined filtrates were concentrated in vacuo to yield 2,3-bis(bromomethyl)-1 ,4-dimethoxy-benzene (26.8 g, 82.7 mmol) in 99% yield.

The synthetic route of 39021-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOVERSYS AG; SCHNEIDER, Peter; RIEDL, Rainer; TIGGES, Marcel; GITZINGER, Marc; PIEREN, Michel; LEVI, Assaf; SEPHTON, Mark; SCHELLHORN, Birgit; ZUEGER, Patrik; BRAND, Michael; GYGAX, Daniel; SPIES, Peter; WO2014/118361; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7, Product Details of 5414-19-7

(23a) A solution of methyl cyanoacetate (5.0 g, 50.6 mmol), 2-bromoethyl ether (16.9 g, 65.7 mmol), and potassium carbonate (17.5 g, 126.4 mmol) in acetone (100 mL) was heated at reflux overnight. The mixture was cooled, filtered, and concentrated to provide the desired pyran. The crude material was carried on as is.

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-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Duan, Jingwu; King, Bryan W.; Decicco, Carl; Maduskuie JR., Thomas P.; Voss, Mathew E.; US2004/72802; (2004); A1;,
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Related Products of 60876-70-2,Some common heterocyclic compound, 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, molecular formula is C10H13BrO, 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 2 In a one-liter four-necked flask equipped with a stirrer and a reflux condenser, purged with nitrogen and dried was placed 24.3 g (1.0 mol.) of metallic magnesium flakes to which were added 10 ml of anhydrous diethyl ether and 2 ml of ethyl bromide. After confirming initiation of the reaction by bubbling on the surface of the metallic magnesium, a solution of 114.6 g (0.5 mol.) of p-tert-butoxybromobenzene in 400 ml of anhydrous diethyl ether was added dropwise at the refluxing temperature over approximately 1 hour, and stirring was continued for 5 hours to give p-tert-butoxyphenylmagnesium bromide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-(tert-butoxy)benzene, its application will become more common.

Reference:
Patent; HOKKO CHEMICAL INDUSTRY CO., LTD; EP307106; (1989); 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. 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 63057-72-7

4-bromo-3-methoxyphenol 10 (19.8 mmol, 5.80 g) was dissolved infreshly distilled THF (200 mL) in an oven-dried three-neck flask underargon. Temperature was cooled down to -78 oC and the solution wasstirred for 30 minutes before dropwise addition of n-BuLi (1.6N in THF,21.8 mmol, 13.6 mL). Once the addition of n-BuLi was completed, themixture was stirred for another 30 minutes at -78 oC before the dropwise addition of freshlydistilled trimethyl borate (59.4 mmol, 6.75 mL) at this temperature. The reaction mixture wasallowed to warm at room temperature and stirred for 5 h. The temperature was cooled down to-20 oC and HCl 1N was slowly added to reach pH = 2-3. The reaction mixture was allowed towarm at room temperature and extracted three times with EtOAc. The organic layers werecombined, washed with brine, dried with MgSO4 and concentrated in vacuo until precipitationoccurred. An amount of hexanes was then added to maximize precipitation. The solution wasfiltered and the solid was filtered and dried under vacuum. The precipitation/filtration procedurewas repeated twice, yielding a total of 3.72 g (73%) of 4 as a white powder. mp = 184-189 oC.1H-NMR (500 MHz, CDCl3): delta = 4.02 (3H, s), 5.26 (2H, s), 7.01 (1H, d, J = 8.33), 7.31-7.50(5H, m), 7.77 (2H, dd, J = 7.78, 1.28). 13C-NMR (125 MHz, CDCl3): delta =56.05, 70.62, 112.97,117.98, 127.21, 127.96, 128.64, 129.71, 136.81, 149.06, 152.09. 11B-NMR (160 MHz, CDCl3): delta= 27.69. IR (NaCl): numax 1502, 1455, 1398, 1249, 1217, 1183, 1134, 1012, 846, 795, 746,697cm-1. HPLC (Retention time, %): 16.92 min, >99%. HRMS (ESI-TOF, m/z): calcd forC14H14BO3 (M-H2O+H)+ = 241.1033, found 241.1031.

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; Cardinal, Sebastien; Voyer, Normand; Tetrahedron Letters; vol. 54; 38; (2013); p. 5178 – 5180;,
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