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. 54468-86-9, name is 2-Amino-N,N-dimethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Compound c18-3 (1 g, 5 mmol) was placed in a 100 mL three-necked flask and added to N,N-dimethylformamide (20 mL).The ice salt bath was below 0 C, then sodium hydride (0.4 g, 10 mmol) was added and stirred for 15 minutes.Then a solution of compound b2 (0.86 mL, 10 mmol) in N,N-dimethylformamide was added and stirred at room temperature overnight.10mL of water was added, extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate,Concentration through the column gave 0.47 g of a white solid.

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; Zhejiang Tongyuankang Pharmaceutical Co., Ltd.; Wu Yusheng; Zhi Wubin; Wang Xin; Wu Shiyong; Li Jingya; Guo Ruiyun; Zheng Maolin; Liang Apeng; Wang Guohui; Chen Mingtao; Ma Jie; Niu Chengshan; (65 pag.)CN108689994; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 62005-48-5, These common heterocyclic compound, 62005-48-5, name is N-(2,2-Dimethoxyethyl)acetamide, 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.

General procedure: 0086] To a solution of crude N-(2,2-dimethoxyethyl)ethanesulfonamide in acetone: water (1: 1, 4 niL) was added Amberlyst-15 Hydrogen form (1.0 g). The resulting mixture was stirred over two days at room temperature. The suspension was filtered through celite and concentrated under reduced pressure to afford crude N-(2-oxoethyl)ethanesulfonamide (614 mg) as a yellow oil. Used without further purification. 1H NMR (400 MHz, CDC13) delta 9.68 (s, J = 1.1 Hz, 1H), 4.15 (d, J = 5.2 Hz, 2H), 3.07 (q, J = 7.4 Hz, 2H), 1.40 (t, J = 7.4 Hz, 3H).

Statistics shows that N-(2,2-Dimethoxyethyl)acetamide is playing an increasingly important role. we look forward to future research findings about 62005-48-5.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; BRUCELLE, Francois; GEHLING, Victor, S.; KHANNA, Avinash; (74 pag.)WO2018/81343; (2018); A1;,
Amide – Wikipedia,
Amide – 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. 2832-19-1, name is 2-Chloro-N-(hydroxymethyl)acetamide, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-N-(hydroxymethyl)acetamide

(e) 2-chloro-N-[5-(1,1-dimethylethyl)-2-hydroxy-3-methylsulfonylbenzyl]acetamide 13.5 g (0.06 mol) of 4-(1,1-dimethylethyl)-2-methylsulfonylphenol are dissolved in 100 ml of concentrated sulfuric acid. 6.63 g (0.054 mol) of 2-chloro-N-hydroxymethylacetamide are added and the mixture is stirred at room temperature for 10 minutes. It is then poured onto ice-water and the crude product is filtered off with suction and recrystallized from toluene. Colorless crystals of melting point: 134-135 C.

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; Hoechst Aktiengesellschaft; US4661636; (1987); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 220798-52-7, name is 3-Bromomethylbenzenesulfonamide, belongs to amides-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 220798-52-7, category: amides-buliding-blocks

625 mg (2.50 mmol) 3-(bromomethyl)benzenesulfonamide and 851 mg (12.5 mmol) 1H-pyrazole were solved in 25 ml acetonitrile and heated under reflux for 16 h. The cooled solution was poured into water and saturated sodium hydrogencarbonate solution was added until neutral reaction. The aqueous phase was extracted three times with methylenchloride, dried over magnesium sulfate and concentrated in vacuo. To remove impurities of pyrazole the residue was taken up in methylenchloride and washed withabout 10 ml 1 N aqueous hydrochloric acid. After drying and solvent evaporation 310 mg (purity 96.5%, 50.4 % of theory) of 3-(1H-pyrazol-1 -ylmethyl)benzenesulfonamide.

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, 3-Bromomethylbenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AG; GREUL, Joerg; HEIL, Markus; JESCHKE, Peter; MUeLLER, Klaus-Helmut; ILG, Kerstin; MALSAM, Olga; PORTZ, Daniela; WO2015/7668; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, belongs to amides-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 112257-19-9, Application In Synthesis of tert-Butyl methyl(2-(methylamino)ethyl)carbamate

Step 4 Synthesis of (2S,3R,4S,5S,6S)-2-(((S)-6-(5-((S)-4-(((2-((tert-butoxycarbonyl)(methyl)amino)ethyl)(methyl)carbamoyl)oxy)-8-(chloromethyl)-1-methyl-7, 8-dihydro-6H-thieno[3,2-e]indol-6-yl)-5-oxopentanoyl)-8-(chloromethyl)-1-methyl-7,8-dihydro-6H-thieno[3,2-e]indol-4-yl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (47) To a solution of 46 (50 mg, 0.054 mmol) in THF (3 mL) at 0° C., was added a solution of 4-nitrophenyl chloroformate (22 mg, 0.10 mmol) in DCM (0.5 mL), followed by DIPEA (57 uL, 0.33 mmol), and the mixture was stirred at 0° C. for 1 h. To the above mixture was added a solution of 38 [prepared as described J. Med. Chem. 1992, 33, 559-567] (31 mg, 0.16 mmol) in THF (0.5 mL), and the mixture was stirred at 0° C. for 30 min and concentrated in vacuo, and the residue was purified was purified by silica gel chromatography using a gradient of EtOAc (0-100percent) in heptanes to give the product 47 as white solid 56 mg (91percent). LC-MS (Protocol B): m/z 1150.2 [M+NH4], retention time=1.14 minutes

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, tert-Butyl methyl(2-(methylamino)ethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; MADERNA, Andreas; SUBRAMANYAM, Chakrapani; TUMEY, Lawrence N.; CHEN, Zecheng; CASAVANT, Jeffrey M.; (187 pag.)US2016/271270; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 57957-24-1, 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 57957-24-1 as follows.

The compound 1a prepared in Example 2 was a boronized substrate, a different chiral ligand prepared in situ and Rh (nbd)2BF4As a catalyst, under different conditions, the preparation of chiral alpha-amino tertiary borate.The reaction is carried out by reacting alpha-arylalkenamide (1a) (0.3 mmol, 1.0 equiv), [Rh (nbd)2] BF4(0.006 mmol, 2 mol%), chiral ligands (0.006 mmol, 2 mol%), boronic acid pinacol ester (0.45 mmol, 1.5 equiv) and base (0.06 mmol, 0.2 equiv) were added to the dry reaction tube.Add solvent (1 mL).Followed by reaction at 60 C for 12 hours.The reaction was quenched with water (3 mL) and extracted with ethyl acetate (10 mL x 3).The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography.The ee value of the reaction was determined by HPLC (OD-H or AD-H).

According to the analysis of related databases, 57957-24-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Tang Wenjun; Zhao Guoqing; Hu Naifu; (31 pag.)CN106146543; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 250275-15-1, name is cis-2-Boc-Hexahydropyrrol[3,4-c]pyrrole, belongs to amides-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 250275-15-1, Computed Properties of C11H20N2O2

Step 3: (3aR,6a5)-tert-l3utyl 5-(5-(2-chloro-4-(1H-pyrazol-4-yl)phenyl)- 1 ,3,4-thiadiazol-2-yl)hexahy- dropyrrolo[3,4-c]pyrrole-2(1 H)-carboxylate10432] 5-(2-Chloro-4-(1 H-pyrazol-4-yl)phenyl)- 1,3,4-thiadiazol-2-amine (250 mg, 0.9 mmol) was added, portion- wise over about 5 minutes, to a stirred solution of Cu13r2 (241 mg, 1.08 mmol) and tert-butyl nitrite (139mg, 1.35 mmol) in MeCN (5 mE) under nitrogen atmosphere. On completion of the addition, the reaction mixture was lefi to stir at room temperature for 18 hours. The reaction mixture was quenched by addition of saturated NH4C1Q,q) and extracted with EtOAc. The organic phase was separated and concentrated in vacuo to afford 2-bromo-5-(2-chloro-4-(1 H-pyrazol-4-yl)phenyl)-1,3,4-thiadiazole a brown solid, which was used without further purification. A degassed reaction mixture of 2-bromo-5-(2- chioro-4-(1H-pyrazol-4-yl)phenyl)-1 ,3,4-thiadiazole (40 mg, 0.117 mmol), cis-2-boc-hexahydropyrollo[3,4-c]pyrrole (24.86 mg, 0.117 mmol), potassium fluoride (7.48 mg, 0.129 mmol), 1 8-crown-6 (30.9 mg, 0.117 mmol) and DIEA (0.041 ml, 0.234 mmol) in NMP (1 mE) was heated under microwave irradiation at 190 C. for 1 h. Afier cooling to RT, the mixture was filtered through celite, washed with MeOH, and the filtrate was concentrated. The residue was dissolved in DMSO and purified by preparative HPEC under basic conditions to give (3aR,6a5)-tert-butyl 5-(5-(2-chloro-4-(1H-pyra- zol-4-yl)phenyl)-1 ,3,4-thiadiazol-2-yl)hexahydropyrrolo[3, 4-c]pyrrole-2(1H)-carboxylate (10 mg, MS: 473.0 [M+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; NOVARTIS AG; AXFORD, Jake; DALES, Natalie; SUNG, Moo Je; US2014/206661; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 120157-96-2, name is Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate, belongs to amides-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 120157-96-2, Recommanded Product: Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate

Reference Example 63 tert-Butyl 4-hydroxymethylbenzylcarbamate Diisobutylaluminum hydride (25.7 ml, 0.93 M hexane solution) was added dropwise to a THF solution (40 ml) of methyl 4-[N-(tert–butoxycarbonyl)aminomethyl]benzoate (2.54 g) at -78C, followed by stirring at the same temperature for 2 hours. A saturated aqueous ammonium chloride solution (10 ml) and diethyl ether were added dropwise to the reaction solution, followed by stirring at room temperature for 1 hour. Magnesium sulfate was added to the reaction solution, followed by further stirring for 1 hour. After removal of the resulting precipitate by filtration trough celite, the filtrate was concentrated, the thus obtained residue was purified by silica gel column chromatography, and the title compound (1.22 g) was obtained as a colorless oil from the fraction of the elude of n-hexane: ethyl acetate = 10:3. 1H-NMR (400 MHz, CDCl3) delta: 1.43 (9H, s), 4.29 (2H, d, J=5.6 Hz), 4.67 (2H, d, J=5.9 Hz), 4.87 (1H, bs), 7.25 (2H, d, J=8.1 Hz), 7.32 (2H, d, J=8.1 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, molecular formula is C8H7BrFNO, 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. Recommanded Product: 4-Bromo-2-fluoro-N-methylbenzamide

To a stirred solution of 4-bromo-2-fluoro-N-methylbenzamide (6.4 g, 27.5 mmol), 1-aminocyclopropanecarboxylic acid (4.29 g, 42.4 mmol), CuI (1.047 g, 5.5 mmol), K2CO3 (9.50 g, 68.0 mmol), in DMF (64 mL) was added H2O (6.4 mL), triethylamine (0.164 mL, 1.1 mmol) followed by 2-acetyl cyclohexanone (0.717 g, 5.10 mmol). The reaction mixture was stirred at 100 C. overnight. The reaction was monitored by TLC and LCMS. H2O was added, and the aqueous layer was washed with ethyl acetate. The aqueous layer was acidified with 1M citric acid solution (pH?4) and extracted with ethyl acetate. The organic extracts were dried over anhydrous Na2SO4, concentrated under reduced pressure and crystallized with DCM to afford 3.01 g of the title compound as an off-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 749927-69-3, its application will become more common.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; Chakravarty, Sarvajit; Jain, Rajendra Parasmal; US2013/79372; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 774-67-4, 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. 774-67-4, name is 4-Amino-N-isopropylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of compound 178.2. To a solution of 76.4 (0.150 g, 0.35 mmol, 1.0 eq) in 1,4-dioxane (3 mL) was added 178.1 (0.092g, 0.52mmol, l .Oeq) and K2C03 (0.1 lOg, 0.86mmol, 2.5eq). Reaction mixture was degassed for 10 minutes using argon gas, then Pd2(dba)3 (0.03 lg, 0.034mmol, O. leq) and Xantphos (0.042 g, 0.069 mmol, 0.2 eq) were added, and again degassed for 5 minutes. Reaction was stired at 110 C for 2 hours. After completion of the reaction, mixture was poured into water and extracted with EtOAc. Organic layers were combined, dried over Na2S04 and concentrated under reduced pressure to obtain crude which was purified by column chromatography to furnish 178.2 (0.1 lOg, 55.18%). MS (ES): m/z 573.6 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-N-isopropylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics