Month: December 2020

Related Products of 369-25-5,Some common heterocyclic compound, 369-25-5, name is Methyl 3,4-difluorobenzoate, molecular formula is C8H6F2O2, 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.

Intermediate 9: Methyl 4-{(3S)-aminopiperidin-1-yl}-3-fluorobenzoate N -Methylpyrrolidone (40 ml) was added to methyl 3,4-difluorobenzoate (1.29 g, 7.5 mmol), and the mixture was stirred at room temperature. Intermediate 8 (2.6 g, 15.0 mmol) and sodium hydrogencarbonate (4.03 g, 48 mmol) were added thereto, and the mixture was stirred at 110C overnight. Water (70 ml) was added to thereaction solution, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: chloroform: methanol = 8: 2) to give the title compound (0.55 g, 29%).

The synthetic route of 369-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meiji Seika Kaisha, Ltd.; EP1227083; (2002); A1;,
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Application of 91-44-1, A common heterocyclic compound, 91-44-1, name is 7-(Diethylamino)-4-methyl-2H-chromen-2-one, molecular formula is C14H17NO2, 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 25 mL reaction tube, add Na2CO3 (63.6 mg, 0.60 mmol), 69.4 mg (0.30 mmol, 1 equivalent) of compound C-2,After replacing with argon three times, 1 mL of acetone (Acetone) + 1 mL of N, N-methylformamide (DMF) was added.After injecting 132 muL (0.90 mmol) of compound E-1 and stirring under blue light for 24 hours, compound H-2 was obtained with a yield of 95%.

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; Zunyi Medical University; He Chunyang; Mao Ting; Zhao Liang; Li Xiaofei; (13 pag.)CN110642831; (2020); A;,
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Application of 107317-58-8, 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 107317-58-8 as follows.

To a solution of methyl 4-bromo-3-(trifluoromethyl)benzoate (10 g, 35.33 mmol) in THF (100 mL) under nitrogen was added 2 M lithium borohydride in THF (2.309 g, 106.0 mmol). The mixture was heated at reflux. The mixture was cooled to 0C and carefully quenched with 6 N HC1 (aq) (about 20 mL or less) (vigorous in the beginning 3-5 mL) up to pH 3. The mixture was diluted with water (25 mL) and extracted with EtOAc (2X). The combined organics were dried over anhydrous Na2S04and filtered. The filtrate was concentrated in vacuo to dryness to afford the crude (4-bromo-3- (trifluoromethyl)phenyl)methanol as a brown solid.

According to the analysis of related databases, 107317-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SADEQUE, Abu J.M.; BUZARD, Daniel J.; (82 pag.)WO2020/51378; (2020); A1;,
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These common heterocyclic compound, 52273-79-7, name is Ethyl 2-(3-aminophenyl)acetate, 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: C10H13NO2

(3-Amino-phenyl)-acetic acid ethyl ester (0.895 g, 5.0 mmol) and acetyl chloride (0.26 mL, 5.0 mmol) are added to a round bottomed flask containing THF (20 mL), pyridine (0.60 mL) and DMAP (10 mg). The mixture is stirred at room temperature overnight. The clear solution is diluted with EtOAc (200 mL), washed with 1N HCl (3¡Á100 mL) and brine (100 mL), and dried with MgSO4. Solvent is evaporated in vacuo to afford intermediate 14-B as a white solid that is used without further purification

The synthetic route of Ethyl 2-(3-aminophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; US2007/276002; (2007); A1;,
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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 4630-82-4 as follows. Computed Properties of C8H14O2

Example 5; Catalytic hydrogenation of various esters using complex [RuCyT?-BINAP)(S,S-DPEN)]; General procedure for the catalytic hydrogenation of methyl benzoate as substrate: Under argon, a Keim autoclave was charged with [RuCl2(i?-BINAP)(dmf)2] (0.01 mmol, 0.05 mol%) and S5S-DPEN (0.01 mmol, 0.05 mol%) followed by THF (2 ml) and the solution stirred for 5 minutes. Then a solution of the desired ester (20 mmol) in THF (2 ml), followed by more THF (2 x 1 ml), and a solution of tridecane (1 mmol) in THF (2 ml), as internal standard, followed by more THF (2 x 1 ml), were successively added to the autoclave. Finally, solid NaOMe (1 mmol, 5 mol%) was added and the autoclave was pressurised with hydrogen gas at 50 bars and placed in a thermostatted oil bath set at 600C. After the mentioned time, the autoclave was removed from the oil bath, and cooled in a cold-water bath. Then, an aliquot (0.4 ml) was taken, diluted with MTBE (5 ml), washed with aq. sat. NH4Cl (5 ml), and filtered over a plug of celite and analyzed by GC.Table 5 : Hydrogenation of various esters using complex [RuCl^-BINAPX^S-DPEN)]Com/Base: molar ratio in ppm relative to the substrate of complex and base. GC: percent of product analysed by GC in the crude reaction mixture. Reaction conditions: H2 gas (50 bars), 600C, NaOMe as base and THF (2 M).

According to the analysis of related databases, 4630-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FIRMENICH SA; WO2008/65588; (2008); A1;,
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Electric Literature of 150529-73-0, A common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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.

step 1-To a solution of 216a (1.19 g, 5 mmol) in CCl4 (30 mL) was added NBS (1.08 g, 6 mmol) followed by benzoyl peroxide (catalytic quantity). The mixture was heated at 80 C. overnight. Then the mixture was cooled, filtered and the solid washed with hexane. The combined filtrates were concentrated in vacuo to afford 1.58 g (100%) of 216b as yellow oil.

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; Roche Palo Alto LLC; US2008/146595; (2008); A1;,
Ester – Wikipedia,
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Synthetic Route of 685892-23-3, 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 685892-23-3 as follows.

Step 1. Preparation of methyl 2-chloro-6-cyclobutylbenzoate (i-llb).A mixture of methyl 2-bromo-6-chlorobenzoate (i-ha) (750 mg, 3 mmol), (PPh3)4Pd (345 mg, 0.3 mmol) and cyclobutylzinc bromide (12 ml in THF, 6 mmol) were mixed under N2 protection. The mixture was stirred at 70C for 12 h under N2. The mixture was extracted with EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered, concentrated, and purified with chromatography (PE: EtOAc = 50:1) to give 350 mg (61% inLCMS, contained some PPh3) of the title compound. LCMS (ESI) calc?d for C12H13C102 [M+H]: 225, found: 225.

According to the analysis of related databases, 685892-23-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28600; (2014); A2;,
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Related Products of 2901-13-5, These common heterocyclic compound, 2901-13-5, name is Ethyl 2-methyl-2-phenylpropanoate, 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 2: Synthesis of 2-(4-(chloroacetyl)phenyl)-2-methylpropionic acid ethyl esterIn a 5L reaction flask, add 2,2-dimethylphenylacetic acid ethyl ester (542g, 2.8mol), 2L dichloromethane solution. Stir. Add anhydrous aluminum chloride (600g, 4.5mol), then add dropwise a chloroacetyl chloride (318.6g,2.8mol) in 500mL of methylene chloride mixture. After reacting for a period,detection by TLC finish the reaction was stopped, the organic layer was separated, and the organic layer washed with water, saturated sodium bicarbonate solution , washed with saturated sodium chloride solution, dried and concentrated to give 2-(4-(chloroacetyl)phenyl)-2-methylpropionic acid ethyl ester (660g, 87%).

The synthetic route of 2901-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Huawe Medicine Technology Development Co., Ltd.; Xu, Feng; Hu, Dandan; Huang, Hui; Jiang, Yuwei; Zhang, Xiaoqing; (6 pag.)CN104276952; (2016); B;,
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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. 2005-10-9, name is 6H-Benzo[c]chromen-6-one, A new synthetic method of this compound is introduced below., Formula: C13H8O2

Magnesium (0.190 g, 7.50 mmol) was placed into an oven-dried round bottom flask and flushed with Ar for 30 min while stirring. 4-Bromobiphenyl 5 (1.75 g, 7.50 mmol), anhydrous THF (10 mL), and a crystal of I2 were then added and the reaction stirred for 1.5 h under Ar. During this time 6H-benzo[c]chromen-6-one 9 (0.981 g, 5.00 mmol) was dissolved in 10 mL of anhydrous THF in a separate oven dried round bottom flask. The flask was cooled to 0 C with an ice bath and sparged for 30 min with Ar. The arylmagnesium bromide solution was transferred to the solution containing 9 at 0 Cvia cannula under Ar pressure. The cooling bath was removed, and the reaction was stirred for 18 h. 50 mL of sat. NH4Cl was added to the reaction and subsequently extracted 3x with 25 mL of Et2O. The combined organics were dried with Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in25 mL of diethyl ether and cooled to 0 C in an ice bath and stirred very rapidly. A chilled (0 C) solution of 70% perchloric acid in acetic anhydride (1:3 by volume) was slowly added drop-wise to the stirring ethereal solution until a colored precipitate formed. The crude product was filtered and recrystallized in glacial acetic acid to yield orange-yellow needles (1.36 g, 63%). mp 234e236 C. 1H NMR(400 MHz, CDCl3/CF3CO2D): d 8.93 (d, J 8.3 Hz, 1H), 8.87 (d,J 8.3 Hz, 1H), 8.79 (d, J 8.3 Hz, 1H), 8.61 (t, J 8.3 Hz, 1H), 8.36(d, J 8.5 Hz, 2H), 8.29 (d, J 8.5 Hz, 1H), 8.20-8.04 (m, 5H), 7.80-7.77 (m, 2H), 7.61-7.52 (m, 3H). 13C NMR (100 MHz, CDCl3/CF3CO2D): d 183.8, 151.5, 150.0, 143.9, 139.6, 138.1, 136.2, 134.6,134.2, 132.0, 130.8, 129.8, 129.4, 128.6, 127.9, 127.6, 123.1, 123.9,121.5, 120.6, 119.9. IR (ATR) nmax: 1597, 1542, 1069 cm1. HRMS (ESI)m/z calcd for C25H17O [M] 333.1279, found 333.1276.

The synthetic route of 2005-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meyer, Samantha M.; Charlesworth-Seiler, Eva M.; Patrow, Joel G.; Kitzrow, Jonathan P.; Gerlach, Deidra L.; Reinheimer, Eric W.; Dahl, Bart J.; Tetrahedron; vol. 76; 23; (2020);,
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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. 61644-18-6, name is Chloromethyl isobutyrate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Chloromethyl isobutyrate

Example 2 Preparation of 2-((3S,7R,8R,9S)-8-(isobutyryloxy)-3-(3-(isobutyryloxymethoxy)-4-methoxypicolinamido)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)ethyl benzoate (Compound 19) To a mixture of 2-((3S,7R,8R,9S)-3-(3-hydroxy-4-methoxypicolinamido)-8-(isobutyryloxy)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)ethyl benzoate (50 mg, 0.087 mmol), Na2CO3 (15 mg, 0.14 mmol) and NaI (3.09 mg, 0.021 mmol) in acetone (0.6 mL) was added chloromethyl isobutyrate (15.4 mg, 0.114 mmol) slowly at room temperature (about 22 C.). The resulting reaction mixture was warmed to 50 C. and stirred at 50 C. overnight. The solvent was evaporated and the crude residue was purified via flash chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (35 mg, 76%) as an off-white solid: mp 48-50 C.; 1H NMR (300 MHz, CDCl3) delta 8.55 (d, J=7.9 Hz, 1H), 8.26 (d, J=5.5 Hz, 1H), 8.04-7.87 (m, 2H), 7.55 (t, J=7.4 Hz, 1H), 7.43 (t, J=7.5 Hz, 2H), 6.95 (d, J=5.4 Hz, 1H), 5.85-5.62 (m, 2H), 5.41 (s, 1H), 5.26-5.06 (m, 2H), 4.94 (dd, J=9.8, 6.3 Hz, 1H), 4.42-4.19 (m, 2H), 3.92 (d, J=14.3 Hz, 3H), 3.65 (s, 1H), 2.76 (t, J=9.5 Hz, 1H), 2.62 (dt, J=10.8, 5.5 Hz, 1H), 2.58-2.47 (m, 1H), 2.30 (s, 1H), 1.82 (s, 1H), 1.29 (d, J=6.3 Hz, 3H), 1.21 (dd, J=7.0, 0.9 Hz, 6H), 1.13 (d, J=7.0 Hz, 6H); ESIMS m/z 673 ([M+H]+).

According to the analysis of related databases, 61644-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Meyer, Kevin G.; Li, Fangzheng; Renga, James M.; Owen, W. John; Nugent, Benjamin M.; Yao, Chenglin; Wang, Nick X.; US2013/296371; (2013); A1;,
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