Month: March 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. 6290-49-9, name is Methyl 2-methoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H8O3

A 10 L three-necked round bottom flask equipped with a mechanic stirrer and thermometer was charged with a solution of tert-butyl acetate (1612, 13.9 mol) in dry THF (14 L) and cooled to -70 C under N2. A solution of LiHMDS (13.9 L, 13.9 mol) in THF was added at -70 C and the mixture was allowed to stir at -70 C for 1 hour. A solution of 3b (723 g, 6.95 mol) in THF (1 L) was added to the reaction and stirred at -70 C for 0.5 hours. The reaction was quenched by the addition of water (10 L) and the mixture was extracted with EtOAc. The combined the organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo to provide 3c as oil. ?H NMR (400 MHz, CDC13) oe 4.09 (s, 2H), 3.43 (s, 2H), 3.42 (s, 2H),1.47 (s, 9H).

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 6290-49-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GRAHAM, Thomas H.; LIU, Wensheng; YU, Tao; ZHANG, Yonglian; WADDELL, Sherman T.; WAI, John S.; COLEMAN, Paul J.; SANDERS, John M.; EMBREY, Mark W.; WALJI, Abbas; FERGUSON, Ronald Dale II; MARCO, Christina Ng Di; STEELE, Thomas; HU, Lihong; PENG, Xuanjia; WO2015/89847; (2015); A1;,
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46004-37-9, name is Methyl 4-amino-2-chlorobenzoate, belongs to esters-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. Product Details of 46004-37-9

A solution of 818 mg of Sodium Nitrite in 13 mL of water was added dropwise to a solution of 2 g of methyl 4-amino-2-chlorobenzoate in 5 mL of HCl and 15 mL of AcOH at 0 C. The reaction was removed from the ice bath and stirred at room temperature for 15 minutes. Simultaneously a solution of 460 mg of Copper II Chloride Dihydrate in 1 mL of water was added to a saturated solution of sulfur dioxide gas in 10 mL of AcOH at 0 C. The cooled solution containing Copper II Chloride and sulfur dioxide gas was slowly added to the re-cooled initial solution containing Sodium Nitrite. The reaction was warmed to room temperature and stirred until gas no longer evolved. The reaction was filtered through celite and poured into a beaker of stirred icewater until a yellow-orange solid crashed out. The icewater solution was filtered thru a Buchner funnel to collect the methyl 2-chloro-4-(chlorosulfonyl)benzoate precipitate and was dried for 24 hours under vacuum. 1 g of methyl 2-chloro-4-(chlorosulfonyl)benzoate was added to a solution of 2 mL of 2M solution of Ammonia in MeOH and 970 muL DIPEA in 5 mL MeOH. Upon completion the reaction was concentrated, extracted twice with saturated bicarbonate, dried with Magnesium Sulfate, filtered and concentrated to give methyl 2-chloro-4-sulfamoylbenzoate. 777 mg of methyl 2-chloro-4-sulfamoylbenzoate was hydrolyzed via Procedure M to yield crude 2-chloro-4-sulfamoylbenzoic acid. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 91 mg of crude 2-chloro-4-sulfamoylbenzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-sulfamoylbenzamide. MS (Q1) 422 (M)+.

The synthetic route of 46004-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gunzner, Janet L.; Sutherlin, Daniel; Stanley, Mark S.; Bao, Liang; Castanedo, Georgette M.; Lalonde, Rebecca L.; Wang, Shumei; Reynolds, Mark E.; Savage, Scott J.; Malesky, Kimberly; Dina, Michael S.; US2006/63779; (2006); A1;,
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These common heterocyclic compound, 58677-05-7, name is Ethyl 2-amino-5-methylbenzoate, 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. Product Details of 58677-05-7

Example 51; 2-(6-(3-Methoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acidIn a schlenck tube, a mixture of Intermediate 33 (2.55 mmol, 0.71 g), Intermediate 55 (2.57 mmol, 0.46 g), BINAP (0.25 mmol, 0.158 g), Pd2(dba)3 (0.13 mmol, 0.116 g) and NaO1Bu (6.35 mmol, 0.610 g) in toluene (20 ml) was heated at 11O0C for 12 hours, under argon atmosphere. The solvent was evaporated, the solid residue was suspended in water, the pH was taken to 6.5 and extracted with CHCI3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.580 g (yield 65%) of the expected compound. delta 1H NMR (300 MHz, CDCI3): 2.28 (s, 3H)1 2.34 (s, 3H), 3.85 (s, 3H), 6.95 (d, 1 H), 7.08(s, 2H), 7.23 (d, 1 H), 7.36 (t, 1H), 7.58 (s, 1 H), 7.83 (s, 1 H), 8.51 (s, 1 H).ESI/MS (m/e, %): 349 [(M+1) 100].

The synthetic route of Ethyl 2-amino-5-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
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Synthetic Route of 51498-33-0, 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 51498-33-0 as follows.

A mixture of 2-Chlorobenzimidazole (I) (0.9 g, 5.9 mmol) and ethyl-4-amino-cyclohexane carboxylate (1.1 g, 5.4 mmol) were placed in a glass high pressure tube. Diisopropylethylamine (2.8 mL, 16.2 mmol) was added, the reaction vessel was sealed and heated to 200 C. for 4 h and allowed to cool to room temperature. Next was added 5 mL EtOH and heated to dissolve the reaction mixture. The reaction mixture was partitioned between aqueous NaHCO3 and EtOAc, and the organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated. Purification of the crude product on silica gel (gradient, 1:1 hexanes:EtOAc to EtOAc) gave the cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (J) (0.5 g) and the trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (K) (0.5 g). Data for (J): 1H NMR (300 MHz, CDCl3) delta7.28 (br s, 2 H), 7.02 (m, 2 H), 5.16 (br s, 1 H), 4.15 (q, 2 H), 3.97 (br s, 1 H), 2.40 (br s, 1 H), 1.80-1.54 (m, 8 H), 1.22 (t, 3 H); mass spectrum m/z 288 [(M+H)+; calcd for C16H22N3O2: 288].

According to the analysis of related databases, 51498-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thompson, Wayne I.; Claremon, David A.; Munson, Peter M.; McCauley, John A.; US2002/55519; (2002); A1;; ; Patent; Merck & Co., Inc.; US6495561; (2002); B2;,
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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. 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, A new synthetic method of this compound is introduced below., Formula: C11H14O3

To the argonated flask filled with 750 ml of dry THF cooled to -78C, 200 ml (0.5 mol) of 2.5 M n-BuLi hexane solution were added, and then 28 ml (0.533 mol) of acetonitrile were added dropwise. The whole mixture was stirred at -78C for 2 h. To the suspension 77.7 g (0.4 mol) of ethyl 2-benzyloxyacetate obtained above were added dropwise and stirring was continued at -78C for 1 h. The reaction was quenched by adding saturated ammonium chloride solution. The mixture was poured onto ice-water and acidified with 6 M hydrochloric acid. Aqueous phase was extracted with diethyl ether. Combined organic phases were washed with brine and dried over anhydrous magnesium sulphate. Drying agent was filtered off and the solvent was evaporated under reduced pressure. Intermediate XII-1 was used in the next step without purification. MS-ESI: (m/z) calculated for C11H11NO2 [M+H]+: 190.22; determined 190.1.

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:
Patent; CELON PHARMA S.A.; DYMEK, Barbara; ZAGOZDA, Marcin; WIECZOREK, Maciej; DUBIEL, Krzysztof; STANCZAK, Aleksandra; ZDZALIK, Daria; GUNERKA, Pawel; SEKULAR, Mariola; DZIACHAN, Maciej; (70 pag.)WO2016/157091; (2016); 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. 1105187-36-7, name is Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

Methyl 3-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylate (173 mg, 0.45 mmol), 3-acetamido-phenylboronic acid (80 mg, 0.45 mmol), tetrakis triphenylphosphine palladium (0) (26 mg, 0.02 mmol) and potassium carbonate (0.45 ml, 2M aq. solution, 0.90 mmol) were mixed under nitrogen atmosphere in degassed 1,2-dimethoxyethane (4 mL). The reaction mixture was refluxed overnight. Water (10 mL) was added and the mixture was extracted with ethyl acetate (2×15 mL). After drying with MgSO4, filtering and evaporation of the solvent, the product was purified by silica gel flash chromatography (40% ethyl acetate in iso-hexane) to give the desired product (62 mg, 32% yield). ESI-MS [M+H] 395, 393; 1H NMR (400 MHz, ODd3) O 9.05 (br 5, 1 H), 7.75 (m, 1 H), 7.48 (dm, J = 7.7 Hz, 1 H), 7.39 – 7.29 (m, 2H), 7.20 (brs, 1H), 7.14 (brs, 1H), 3.80 (5, 3H), 2.13 (5, 3H).

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 1105187-36-7.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; GISING, Johan; LINDSTROM, Stefan; ANTONOV, Dmitry; BRANDT, Peter; BELFRAGE, Anna Karin; BREM, Juergen; SCHOFIELD, Christopher J.; (161 pag.)WO2018/215800; (2018); A1;,
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Synthetic Route of 107045-28-3,Some common heterocyclic compound, 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, molecular formula is C12H17NO2, 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 5-bromo-2-iodobenzoic acid (5. 00g, 15. [3MMOL)] in dimethylformamide [(60ML)] was treated with EDAC. [HC1] (3.. [51G, 18. 4MMOL), 1-] [HYDROXYBENZOTRIAZOLE] hydrate (2. [48G,] 18. 4mmol), and 4-aminomethylbenzoic acid tert-butyl ester (3.74g, 18. [4MMOL),] then stirred overnight at room temperature. The solution was treated with water [(40ML),] saturated aqueous sodium bicarbonate solution (15mL), followed by water [(40ML)] and the mixture stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and allowed to air dry overnight. The solid was heated in hexanes/ethyl acetate 2: 1, cooled to room temperature, and the crystals collected by filtration. Drying afforded the product as 6.30g of white solid (79.8% yield). [1H-NMR] [(CDC13)] ; d 7.98-7. 96 (d, [2H),] 7.70-7. 68 (d, 1H), 7.53-7. 52 (d, [1H),] 7.44-7. 43 (d, [2H),] 7.24-7. 21 (dd, 1H), 6.13 (bs, 1H), 4.67 (d, 2H), 1.60 (s, [9H).] MS: M+ +1 = 515.9/517. 9 Da.

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

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/14379; (2004); A1;,
Ester – Wikipedia,
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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. 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H14F2O2

Under nitrogen atmosphere, 2.3 g of ethyl 4,4- difluorocyclohexanecarboxylate was dissolved in 50 ml of tetrahydrofuran. Thereto 0.46 g of lithium aluminum hydride was added at 0C and the mixture was stirred at 0C for an hour. Thereafter, 1N aqueous sodium hydroxide was added to the reaction mixture, and formed solids were filtered and then washed with ethyl acetate. The filtrate and the washing solution were combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain (4, 4-difluorocyclohexyl) methanol.

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; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2005/63694; (2005); A1;,
Ester – Wikipedia,
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Application of 40872-87-5,Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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 methyl 3-amino-4-chlorobenzoate (3.00 g, 16.2 mmol) and l-(morpholin-4- yl)cyclopropanecarboxylic acid hydrochloride (1:1) (example 65A, 6.71 g, 32.3 mmol, 2 equiv) in DMF (50 mL) was added (benzotriazol-l-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PYBOP, 16.8 g, 32.3 mmol, 2 equiv) and diisopropylethylamine (14.1 mL, 80.8 mmol, 5 equiv). The resulting mixture was stirred at room temperature for 3 days. (Benzotriazol-1- yloxy)tripyrrolidinophosphonium hexafluorophosphate (PYBOP, 16.8 g, 32.3 mmol, 2 equiv) and diisopropylethylamine (14.1 mL, 80.8 mmol, 5 equiv) were added and the resulting mixture was stirred at 60 C over night. The mixture was concentrated under reduced pressure, was then dissolved in dichloromethane, was washed with IN aqueous hydrogen chloride solution and saturated, aqueous sodium bicarbonate solution, was dried over sodium sulfate and concentrated under reduced pressure. The remaining solids were then triturated with ethanol (40 mL), and the resulting mixture was stirred for 30 minutes. The remaining solids were removed by filtration, washed with ethanol, and were dried at 50 C under reduced pressure. The remaining solids were then triturated with ethanol (70 mL), and the resulting mixture was stirred under reflux. After cooling to room temperature, the remaining solids were removed by filtration, washed with ethanol, and were dried at 50 C under reduced pressure to give the title compound (3.60 g). LC-MS (Method 4): Rt= 1.23 min; MS (ESIpos): m/z = 339 [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 Methyl 3-amino-4-chlorobenzoate, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; SCOTT, William Johnston; BENDER, Eckhard; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; WO2014/147182; (2014); A2;,
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Related Products of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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.

Indoline (9a) (1.6 mL, 12.9 mmol) was added dropwise with stirring to triethyl methanetricarboxylate (3.2 mL, 12.9mmol) heated to 215C, at such a rate that the temperature of the reaction mixture was maintained within ¡À5C of the initial temperature. The ethanol eliminated during the reaction was distilled through a suitable still-head. After adding all the indoline the reaction mixture was maintained at the same temperature for 10-15 min, after which it was cooled. The solid ester 5a was filtered off, washed with water, and dried. Yield 1.3 g (38%); mp 303.0 -304C LC-MS (M+1) 260.4 1H NMR (300 MHz, DMSO) delta 13.10 (s, 1H), 7.68 (d, J = 8.2 Hz, 1H), 7.52 (d, J = 7.1 Hz, 1H), 7.22 – 7.13 (m, 1H), 4.33 (q, J = 7.1 Hz, 2H), 4.26 – 4.16 (m, 2H), 3.37 (s, 1H), 3.32 (s, 1H), 1.31 (t, J = 7.1 Hz, 3H).

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

Reference:
Article; Huddar, Srigouri; Jang, Soojin; Kim, Hyung Jun; Lee, Sunkyung; Park, Chul Min; Bioorganic and medicinal chemistry letters; (2020);,
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