Month: March 2021

Reference of 54616-47-6, A common heterocyclic compound, 54616-47-6, name is 2-Bromo-N,N-dimethylbenzamide, molecular formula is C9H10BrNO, 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: To a stirred solution of 1 (0.23 g, 1.0 mmol) in THF (6 mL) at -78C was added n-BuLi (1.6 M in hexane; 1.0 mmol) dropwise. After 15 min, PhNCS(0.14 g, 1.0 mmol) was added and stirring was continued for an additional 5 min before addition of saturated aqueous NH4Cl (15 mL). The mixture was extracted with AcOEt (3 ¡Á 10 mL), and the combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated by evaporation

The synthetic route of 54616-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kobayashi, Kazuhiro; Shigemura, Yuuho; Fujiwara, Daiki; Heterocycles; vol. 94; 6; (2017); p. 1152 – 1158;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 138-41-0, name is Carzenide, 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 138-41-0, Application In Synthesis of Carzenide

Tolylsulfonamide 10 (1.00mM) was first converted to 4-aminosulfonyl benzoic acid by refluxing its aqueous suspension with KMnO4 (3.00mM) to generate the corresponding carboxylic acid followed by refluxing its methanolic solution firstly in acidic condition and then in excess of hydrazine hydrate.37 Yield 74%, lit. mp: 230-232C, Obs. mp: 228-230C.

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, Carzenide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sitaram; Celik, Gulsah; Khloya, Poonam; Vullo, Daniela; Supuran, Claudiu T.; Sharma, Pawan K.; Bioorganic and Medicinal Chemistry; vol. 22; 6; (2014); p. 1873 – 1882;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 97-35-8,Some common heterocyclic compound, 97-35-8, name is 3-Amino-N,N-diethyl-4-methoxybenzenesulfonamide, molecular formula is C11H18N2O3S, 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 Production of 3-amino-N,N-diethyl-4-hydroxybenzenesulfonamide 3-Amino-N,N-diethyl-4-methoxybenzenesulfonamide (5 g) was dissolved in methylene chloride (150 mL). Under ice-cooling, boron tribromide (1.0 M methylene chloride solution, 38.7 mL) was added dropwise, and the mixture was stirred overnight at room temperature. Water (150 mL) was added dropwise to the reaction mixture under ice-cooling, and the aqueous layer was washed with chloroform. The obtained aqueous layer was weak acidified with 4N aqueous sodium hydroxide under ice-cooling. The precipitated solid was collected by filtration to give the title compound (4.0344 g) as a pale-beige solid.

The synthetic route of 97-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; US2008/64871; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 21744-84-3,Some common heterocyclic compound, 21744-84-3, name is 4-Methyl-2H-1,4-Benzoxazin-3-one, molecular formula is C9H9NO2, 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 cooled solution of 2H-1,4-benzoxazin-3(4H)-one (11.93 g, 80 mmol) in N,N-dimethylformamide (120 ml) was added sodium hydride (60% dispersion in mineral oil, 3.2 g, 80 mmol) in portions between 0 C. and 5 C. (1 h).The mixture was stirred 1 h at 0 C. To the cooled mixture was added ethyl iodide (13.7 g, 88 mmol) dropwise. The ice bath was removed and the mixture was stirred at r.t. for 17 h. The mixture was poured on water and extracted twice with AcOEt. The organic layers were washed with brine and water, dried (MgSO4) and concentrated. The crude product was purified by column chromatography (silica gel, heptane/AcOEt 9:1) to give the title compound (13.3 g) as colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-2H-1,4-Benzoxazin-3-one, its application will become more common.

Reference:
Patent; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249124; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1092522-02-5, name is tert-Butyl (4-aminophenyl)(methyl)carbamate, molecular formula is C12H18N2O2, 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. HPLC of Formula: C12H18N2O2

General procedure: HBTU (1.82g, 3.59mmol), DIPEA (0.84mL, 4.80mmol) and monomethyl suberate (0.93mL, 5.28mmol) were added to a solution of 34 (1.0g, 4.80mmol) in DMF (10mL) and the mixture was stirred for 12hat rt. Then the reaction was quenched with H2O and extracted using EtOAc, dried over MgSO4 and passed through a filter column to give corresponding ester which was dissolved in the minimum amount of dioxane. H2O with pH adjusted to 3 using 3N HCl was added and the reaction mixture was stirred at reflux overnight to yield the corresponding free amine. The reaction was basified and extracted using EtOAc, then dried, concentrated and passed through a filter column to give the free amine. To a solution of this free amine (1.0g, 3.59mmol) in DMF (10mL) was added HBTU (1.36g, 3.59mmol), DIPEA (0.66mL, 3.59mmol) and 1,4-dibenzyloxy-5-isopropyl benzoic acid (0.76g, 4.31mmol) and the solution was stirred for 12hat 80C. The reaction mixture was quenched with H2O and extracted with EtOAc (25mL¡Á3). The combined organic layer was collected, dried over anhydrous MgSO4 and concentrated under reduced pressure to give a light yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1: 1) to give 42 as a colorless liquid in 65% yield (overall from 34)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1092522-02-5, its application will become more common.

Reference:
Article; Mehndiratta, Samir; Lin, Mei-Hsiang; Wu, Yi-Wen; Chen, Chun-Han; Wu, Tung-Yun; Chuang, Kuo-Hsiang; Chao, Min-Wu; Chen, Yi-Ying; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 185; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, 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 121492-06-6, name: N-Boc-(2-Aminoethyl)-N-methylamine

EXAMPLE H-l 4 Example H-14 N-ethyl-N-(2-((4-(2-hvdroxypropan-2-yl)pyrinudin-2-yl)(methyl)aniino)ethyl)-2- isopropoxynicotinamide Step 1 : tert-butyl (2-(((benzyloxy)carbonyl)amino)ethyl)(methyl)carbamate (H-7) To a solution of tert-butyl (2-aminoethyl) (methyl)carbamate (5.0 g, 28.7 mmol) in THF (100 mL) was added NaHC03 (12.1 g, 143.5 mmol) at 0 C. The resulting mixture was stirred at the same temperature for 15 min. Cbz-Cl (5.9 g, 34.4 mmol) was added dropwise. The mixture was stirred at RT overnight, then filtered and the filtrate was concentrated in vacuo. The residue was purified by combiflash (10% EtOAc in petroleum ether) to give the title compound H-7. LRMS m/z (M+H) 309.1found, 309.4 required.

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, N-Boc-(2-Aminoethyl)-N-methylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 16695-22-0, A common heterocyclic compound, 16695-22-0, name is (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate), molecular formula is C25H29NO8S3, 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.

In a 50 ml three-neck bottle are sequentially added myricitrin in (509 mg, 1 . 6mmol), DMF (15 ml), K2CO3(276 mg, 2 . 0mmol), heating to 110 C, and then is slowly dripped N, N-bis [2 – (P-sulfonyloxy) ethyl]-P-toluene sulfonamide (454 mg, 0 . 8mmol) solution of DMF (15 ml), constant temperature 110 C reaction 3-5h (TLC tracking of the reaction, developing agent is petroleum ether (PE): ethyl acetate (EA): formic acid (HCOOH) =10:10:1, v/v), the reaction solution is poured into the acetic acid ethyl ester (30-60mL) in, filtered, concentrated under reduced pressure to get the crude product, the crude product by silica gel chromatography purification column or half preparation HPLC method, drying, HTEMY obtained compound (402 mg). The preparation method of this invention has the synthetic steps are simple, low cost, mild condition, and the like.

The synthetic route of 16695-22-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo Institute of Technology, Zhejiang University; Gao, Kun; Wu, Yuechan; Chen, Jia; (9 pag.)(2016);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 106984-09-2, 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. 106984-09-2, name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Sodium hydride (7.2 g, 0.3 mol) was weighed in a three-necked flask,Add 200 ml of tetrahydrofuran, cool to 0 or less,BOC-NH-PEG4 (29.3 g, 0.1 mol) was slowly added dropwise,Control the reaction temperature is about 0 . After 1 hour, continue to cool to -5 ,Slowly dropwise 3-bromopropionic acid (15.3 g, 0.1 mol) was added to control the reaction below 0 ,After the completion of the reaction at room temperature for 24 hours, with dilute hydrochloric acid PH value of 3-4,Ethyl acetate was extracted three times, the combined extracts were dried,Boc-NH-PEG4-CH2CH2COOH (23 g yield 63%) was recovered under reduced pressure.Boc-NH-PEG4-CH2CH2COOH (7.3 g, 0.020 mol) was dissolved in 50 mL of tetrahydrofuran,Slowly add 2mol / L hydrochloric acid solution (20mL),And stirred at room temperature overnight. The next day, add 50mL of ethyl acetate,And then extracted with ethyl acetate water phase once,The water phase evaporated to dry NH2PEG4-CH2CH2COOH hydrochloride crude,And then crystallized from ethyl acetate to give pale yellow crystals(3.92 g, Yield: 65%)

The synthetic route of tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Furuikang Biological Technology Co., Ltd.; Luo Qiandong; Hu Deyin; (7 pag.)CN104774161; (2017); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 94838-59-2, These common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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.

A mixture of 3-(4-methylpiperazin-l-yl)propanoic acid (172 mg, 1 mmol), HATU (456 mg, 1.2 mmol), DIPEA (323 mg, 2.5 mmol) and /ert-butyl 4-aminophenethylcarbamate (236 mg, 1 mmol) in DCM (10 mL) was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as yellow solid (90mg, 23.0% yield). NMR (500 MHz, DMSO-riri) S: 10.01 (s, 1H), 7.48 (d, J= 8.4 Hz, 2H), 7.10 (d, J= 8.4 Hz, 2H), 6.84 (dd, J= 13.1, 6.9 Hz, 1H), 3.10 (dd, J= 14.1, 6.4 Hz, 2H), 2.64 (dd, .7= 24.9, 17.1 Hz, 6H), 2.45 (dd, J= 15.8, 8.8 Hz, 8H), 2.20 (d, J= 12.1 Hz, 3H), 1.37 (d, J= 1.6 Hz, 9H).

The synthetic route of 94838-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 4141-08-6, 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. 4141-08-6, name is 2-Amino-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Dissolve 2-amino-N-methylbenzamide (1.26g, 8.4mmol) and 2,4-dichloro-5-methylpyrimidine (0.93ml, 8mmol) in anhydrous DMF (6ml) under ice bath 60% NaH (0.38g, 9.6mmol) was added and stirred at room temperature for 24h. After the end, water was added dropwise to terminate the reaction, extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by silica gel column (eluted with ethyl acetate / petroleum ether) to obtain 0.88 g of yellow solid with a yield of 40%.

The synthetic route of 2-Amino-N-methylbenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Xibo Pharmaceutical Co., Ltd.; Yin Yuxin; Su Yue; (37 pag.)CN111072571; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics