Tag: M.W=200-300

Reference of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, molecular formula is C7H13BrO2, 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 No.16: Preparation of tert-butyl 3,3′-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)phenylsulfonylazanediyl)dipropanoate and tert-butyl 3-(4-(3-(3-chloro-4- isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)phenylsuIfonamido)propanoate; To a solution of 4-(3-(3-chloro-4-isopropoxyphenyI)-l,2,4-oxadiazol-5- yl)benzenesulfonamide (0.500 g, 1.270 mmol) in DMF (3.17 ml) was added NaH (0.056 g, 1.396 mmol). After about 10 min. tert-butyl 3-bromopropanoate (0.233 ml, 1.396 mmol) was added and the reaction mixture was heated to about 600C. After about 48h the reaction mixture was cooled to room temperature and purified by chromatography on silica gel (eluting with EtO Ac/Hep) to provide tert-butyl 3,3′-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)phenylsulfonylazanediyl)dipropanoate (0.24 g, 29%) as a colorless solid. LCMS (Table 1, Method c) R, = 3.43 min, m/z 667 (M+NH»)+. In addition to tert-butyl 3-(4- (3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)phenylsulfonamido)propanoate (0.28 g, 42%) as a colorless solid. LCMS (Table 1, Method c) R1 = 3.13 min, m/z 521 (M-H)’.

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/76356; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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. Recommanded Product: Methyl 4-chlorosulfonylbenzoate

Example 5-35a Methyl 4-(N-(4-methoxyphenyl)sulfamoyl)benzoate To 4-methoxybenzenamine (580 mg, 4.71 mmol) and triethylamine (1.48 mL, 10.7 mmol) in dichloromethane (10 mL) was added methyl 4-(chlorosulfonyl)benzoate (1.00 g, 4.28 mmol). This mixture was stirred for 16 hours at room temperature. The reaction was diluted with dichloromethane (50 mL) and washed consecutively with water, 10% citric acid, and brine. The organics were dried over sodium sulfate and concentrated via rotovap. The resulting crude material was chromatographed on silica gel using 100% dichloromethane as eluent affording Methyl 4-(N-(4-methoxyphenyl)sulfamoyl)benzoate as a white crystalline solid (400 mg, 30% yield)

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Senomyx, Inc.; US2009/274632; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 54535-22-7

Step b :4-hydroxyquinoline 3- carboxylic acid ethyl ester A clean and dry I liter round bottom flask, fitted with mechanical stirrer and thermo pocket was charged 2-Phenylaminotnethylene malonic acid diethyl ester (100 g) and Eaton’s reagent (400 ml) at room temperature. The reaction mass was heated to 80-90 C. and maintained under stirring for 4-6 hours at the same temperature. After completion, the reaction mass was cooled to 5-10 C. and was treated with aqueous sodium carbonate solution at 0-10 C. and stirred for 60-90 minutes at the same temperature. The resultant solid was filtered, washed with water (until the water filtrate showed neutral pH) and dried at 45-50 for 6-8 hours to obtain 4-hydroxyquinoline 3-carboxylic acid ethyl ester (70-80 g)

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Optimus Drugs Private Limited; Desi Reddy, Srinivas Reddy; Rane, Dnyandev Ragho; Velivela, Venkata Srinivasa Rao; (11 pag.)US2017/96397; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-bromo-3-fluorobenzoate

Step 1: methyl 4-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H- pyrrolo[2,3-d]pyrimidin-4-yl)-lH-pyrazol-l-yl]azetidin-l-yl}-3-fluorobenzoate2,2′-Bis(diphenylphosphino)-l,l’-binaphthyl (0.11 g, 0.18 mmol) was added to a mixture of {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3- d]pyrimidin-4-yl)-lH-pyrazol-l-yl]azetidin-3-yl}acetonitrile dihydrochloride (0.86 g, 1.8 mmol), methyl 4-bromo-3-fluorobenzoate (0.50 g, 2.1 mmol, Combi-Blocks: Cat.No.CA-4107), and cesium carbonate (1.7 g, 5.4 mmol) in toluene (25.0 mL) under N2, followed by palladium acetate (0.040 g, 0.18 mmol). The reaction mixture was stirred at 120C for 5 hours. The reaction mixture was diluted with ethyl acetate, filtered, and concentrated under reduced pressure to afford the desired crude product (1.06 g) which was directly used in next step reaction without furtherpurification. LCMS (M+H)+: m/z = 562.3.

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; INCYTE CORPORATION; YAO, Wenqing; BURNS, David M.; ZHUO, Jincong; WO2012/177606; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 41841-16-1, 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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of the methyl 2-bromophenylacetate (0.86 ml; 5.31 mmol) in dichloromethane (10.2 ml, 159 mmol) are added N- bromosuccinimide (1 .04 g, 5.84 mmol) and azobisisobutyronitrile (43.6 mg, 0.27 mmol) at room temperature and the mixture is stirred at 100 C for 16 h under argon atmosphere. The reaction mixture is cooled down to room temperature. The mixture is diluted with diethyl ether and filtered. The filtrate is evaporated to dryness. The oily residue containing solid succinimid is diluted with heptane and filtered again. The solvent is removed to afford methyl 2-bromo-2-(4-bromophenyl)acetate (1 .38 g, 4.56 mmol, 86 % of theory).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(4-bromophenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; SCHRAUB, Martin; DOBELMANN-MARA, Lars; RIEDMUELLER, Stefan; (326 pag.)WO2018/149852; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-bromo-4-fluorobenzoate

To a solution of methyl 2-bromo-4-fluorobenzoate (1.2 g, 5.15 mmol) in DMF (5 mL) was added cyanocopper (0.92 g, 10.3 mmol) under N2. The reaction was stirred at 120 C for 1.5 h under N2. Then, the reaction was cooled to room temperature.10% NaCN (10 mL) was added to the reaction. The mixture was extracted with DCM (3 x 30 mL). The layers were separated and the organic phase was washed with saturated aqueous NaCl (3 x 50 mL) .The combined organic layers were dried over Na2SO4. After filtration, 850 mg of product was obtained as a white solid.

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; HEFFERNAN, Michele L.R.; HARDY, Larry Wendell; BROWN, Scott P.; HERMAN, Lee W.; (180 pag.)WO2018/26371; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 79025-26-6,Some common heterocyclic compound, 79025-26-6, name is Methyl 2-amino-5-chloro-4-methoxybenzoate, molecular formula is C9H10ClNO3, 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 mixture of compound 2 (26 g, 167 mmol) in a solution of NaOH (13.4 g, 0.334 mmol) in water (400 mL) was stirred at r.t. overnight, after which time complete reaction was observed by TLC. The reaction was acidified with 2N HCl and filtered, washed with water, and dried to provide the desired product as a white solid (30 g, 90% yield). NMR (400 MHz, DMSO-d6) delta: 7 62 (IH, s), 6.44 (IH, s), 3.80 (3H, s).

The synthetic route of 79025-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEREPEUT, INC.; LU, Bingwei; (43 pag.)WO2019/55528; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate, belongs to esters-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 139102-34-4, Recommanded Product: Methyl 4-bromo-2-methoxybenzoate

To a degassed solution of methyl 4-bromo-2-methoxybenzoate (0.70 g, 2.86 mmol) in 1,4-dioxane (10 mL) and MeOH (2.5 mL) at room temperature under nitrogen blanketing is added 4-chlorophenyl boronic acid (0.536 g, 3.43 mmol), Pd(dppf)Cl2 (0.233 g, 0.286 mmol) and K3PO4 (0.728 g, 3.43 mmol). The resulting suspension is heated to 80 C. and stirred for 3 hours after which the reaction is cooled to room temperature and filtered through Celite. The collected solids are washed with additional MeOH and the filtrate concentrated under reduced pressure. The crude material is purified over silica (hexanes:EtOAc gradient 6:1 to 4:1) to afford 0.614 g (78% yield) of the desired product as orange crystals. 1H NMR (400 MHz, CDCl3) delta ppm 7.89 (1H, d, J=8.0 Hz), 7.52-7.56 (2H, m), 7.44 (2H, d, J=8.7 Hz), 7.17 (1H, d, J=8.0 Hz), 7.12 (1H, d, J=1.6 Hz), 3.99 (3H, s), 3.92 (3H, s). HPLC-MS: m/z 277 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; The Procter & Gamble Company; US2007/299086; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 135484-83-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 135484-83-2, name is Methyl 2-amino-4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 2-amino-4-bromobenzoate (15 g, 65 mmol) in trifluoroacetic acid (75 mL) and concentrated HC1 (15 mL) was cooled in an ice water bath. To it sodium nitrite (9.0 g, 130 mmol) in water (15 mL) was added via addition funnel over 15 mm. The reaction stirred at 0 C for 30 mm. Then sodium azide (13 g, 196 mmol) was slowly addedportion-wise. The reaction was stirred at 0 C to rt for 1.5 hrs. The solvents were removed and H20 and EtOAc were added. The layers were separated and the organic layer was washed with saturated NaHCO3 three times and dried over Na2SO4. The solvent was removed and the crude material was purified by chromatography thru a Si02 using a solvent gradient of 100 % Hx to 20 % EtOAc / Hx to afford the title compound (16 g, 61mmol, 95 %). ?H NMR (400 MHz, CDC13) oe ppm 7.74 (d, J 8.4 Hz, 1H), 7.38 (d, J 1.8 Hz, 1H), 7.34 – 7.29 (m, 1H), 3.90 (s, 3H).

The synthetic route of Methyl 2-amino-4-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; KICK, Ellen, K.; BODAS, Mandar; MOHAN, Raju; BUSCH, Brett, B.; AVERBUJ, Claudia; VALENTE, Meriah; WURTZ, Nicholas; RAO, Prasanna Savanor, Maddu; SHETTY, Jeevanprakash; VENU, Alla; WO2014/152738; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, molecular formula is C8H11NaO5, 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. Application In Synthesis of Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate

Preparation of 6-hydroxy-2-phenylpyrimidine-4-carboxylic acid:; Diethyl oxaloacetate sodium salt 4.84 g (23.0 mmol) was added to a solution of 16 mL of water and 4 mL of ethanol. The suspension was stirred for 5 min, then a solution of 3.6 mL (22.5 mmol) of 6.25 M NaOH(O(? ) was added. The mixture was stirred at ambient temperature for 15 minutes to give a tan solution. To this was added a solution of 3.01 g (19.2 mmol) of benzamidine hydrochloride in 15 mL of H2O, giving a solution with pH=l 1. Next, 1 mL of 6.25 M NaOH was added, pH = 1 1 when done, then the reaction was stirred at 80 C for 2 h. Additional NaOH was added during the heating period to maintain the pH between 1 1 and 12. (A total of about 10 mmol additional NaOH was added.) The reaction was cooled to 5 C, then 12M HCl was added until pH = 1. The white precipitate was collected, washed with water, and dried on the filter to give 3.09 g (74%) of the product as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40876-98-0, its application will become more common.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2009/61453; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics