Month: February 2021

Synthetic Route of 127828-22-2, These common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 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: (S)-4-(4-chlorophenyl)-6-(2-methoxy-2-oxoethyl)-3 ,9-dimethyl-6H-thieno [3,2- fj [1 ,2,4jtriazolo[4,3-aj [1 ,4jdiazepine-2-carboxylic acid (CAS 916493-82-8) (44 mg, 0.1 mmol), mono-Boc-amino-PEG-amine (1.5 eq), HATU (1.5 eq), and N,Ndiisopropylethylamine (1.5 eq) were added to DMF (0.1 M). The mixture was stirred for 4 hours at room temperature. The mixture was diluted with ethyl acetate, washed with iN NaOH and brine, dried over Na2504, filtrated and concentrated under reduced pressure. The residue was purified by flash chromatography to give mono-amides (93%). The mono-amide was dissolved into dichloromethane (0.5 M). Trifluoroacetic acid (0.5 M) was added to the solution. The mixture was stirred for 1 hour at room temperature. The mixture was diluted with dichloromethane, washed with iN NaOH, dried over Na2504, filtrated and concentrated under reduced pressure. The free amine was used for the next step without purification. The free amine, (S)-4-(4-chlorophenyl)-6-(2-methoxy-2-oxoethyl)-3 ,9-dimethyl-6H-thieno [3,2- fj [1 ,2,4jtriazolo[4,3-aj [1 ,4jdiazepine-2-carboxylic acid (CAS 916493-82-8) (1.1 eq), HATU (1.5 eq), and N,N-diisopropylethylamine (1.5 eq) were added to DMF (0.1 M). The mixture was stirred for 4 hours at room temperature. The mixture was diluted with ethyl acetate, washed with iN NaOH and brine, dried over Na2504, filtrated and concentrated under reduced pressure. The residue was purified by flash chromatography to give the titled compounds (55%, for 2 steps).

The synthetic route of 127828-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; QI, Jun; TANAKA, Minoru; ROBERTS, Justin, M.; (314 pag.)WO2017/91673; (2017); A2;,
Amide – Wikipedia,
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194920-62-2, name is tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate, belongs to amides-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: tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate

General procedure: Oxime 1 (20 mg, 51.5 mumol) and HOBt.H2O (7.9 mg, 51.5 mumol)were dissolved in 1.5mL of DMF and DIC (8 muL, 51.5 mmol) wasadded. It was stirred for 5 min, then tert-butyl 2-aminoethylcarbamate hydrochloride (20 mg, 102 mumol) and DIEA(18 muL, 102 mumol) were added to the solution. The mixture wasstirred at 50 C for 16 h then it was evaporated in vacuo. The crudeproduct was purified by column chromatography on silica gel 60with CHCl3-MeOH (8:2) to give 22.2 mg (81%) of 2 as yellowish oil.

The synthetic route of 194920-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dvoracsko, Szabolcs; Keresztes, Attila; Mollica, Adriano; Stefanucci, Azzurra; Macedonio, Giorgia; Pieretti, Stefano; Zador, Ferenc; Walter, Fruzsina R.; Deli, Maria A.; Kekesi, Gabriella; Banki, Laszlo; Tuboly, Gabor; Horvath, Gyoengyi; Toemboely, Csaba; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 571 – 588;,
Amide – Wikipedia,
Amide – 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. 77925-80-5, name is N-(Benzyloxy)-2-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 77925-80-5

[0232] A solution of 2-nitrobenzene-1-sulfonyl chloride (500 g, 2.26 mol) in pyridine (1500 mL) was added dropwise to a solution of O-benzylhydroxylamine hydrochloride (400 g, 2.51 mol) in pyridine (1500 mL) at 0 C. The reaction mixture was then stirred at 20 C. overnight. The mixture was concentrated in vacuum, diluted with DCM and washed with HCl (10%) three times. The combined organic layer was concentrated in vacuum and re-crystallized with DCM to afford N-(benzyloxy)-2-nitrobenzenesulfonamide (485 g, 62.6%) as a yellow solid. [0233] To a solution of N-(benzyloxy)-2-nitrobenzenesulfonamide (212 g, 0.69 mol) in THF (1000 mL) was added (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate (171 g, 0.63 mol) and PPh3 (275 g, 1.05 mol), followed by dropwise addition of a solution of DEAD (195 g, 1.12 mol) in THF (500 mL). The mixture was then stirred at 20 C. overnight. The reaction mixture was then concentrated in vacuum and purified by silica gel column chromatography (3:1 petroleum ether/EtOAc) to afford (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate (283.8 g, 80%) as a yellow oil.

According to the analysis of related databases, 77925-80-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gu, Yu Gui; He, Yong; Yin, Ning; Alexander, Dylan C.; Cross, Jason B.; Busch, Robert; Dolle, Roland E.; Metcalf, III, Chester A.; US2013/296555; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 40545-33-3, These common heterocyclic compound, 40545-33-3, name is 2-Amino-5-methylbenzamide, 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 cold (0-5 C) stirred suspension of aminobenzamides 10a-c (0.016 mol) in pyridine (13 ml), 0.016 mol of the appropriate 3-phenylacryloyl chloride 11c-k was added over 30 min. After addition was complete, the solution was stirred for 24 h and then poured onto crushed ice. The precipitate was removed by filtration, washed with water, and crystallized from ethanol.

Statistics shows that 2-Amino-5-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 40545-33-3.

Reference:
Article; Raffa, Demetrio; Maggio, Benedetta; Plescia, Fabiana; Cascioferro, Stella; Plescia, Salvatore; Raimondi, Maria Valeria; Daidone, Giuseppe; Tolomeo, Manlio; Grimaudo, Stefania; Di Cristina, Antonietta; Pipitone, Rosaria Maria; Bai, Ruoli; Hamel, Ernest; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2786 – 2796;,
Amide – Wikipedia,
Amide – 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. 2227-79-4, name is Benzothioamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 2227-79-4

1) 2.33 g of thiobenzamide was dissolved in 20 ml of dry methanol, and 2.16 g of 1,3-dichloroacetone was added thereto at room temperature and then heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, and ice water was added to the remaining product, which was then neutralized with an aqueous solution of sodium hydrogen carbonate. The resulting product was extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 2.03 g of 4-chloromethyl-2-phenylthiazole was obtained from the fraction eluted with chloroform/n-hexane=1/2.

The synthetic route of 2227-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissan Chemical Industries, Ltd.; US6063734; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 116332-54-8 as follows. category: amides-buliding-blocks

a 4-Fluoro-2-(2-methylthio-4-pyrimidyl)acetophenone nBuLi (10 ml of a 1.6 M solution in hexane; 12 mmol) is added at -78 C. to a solution of diisopropylamine (2.48 ml; 17 mmol) in THF (15 ml) and stirred for 5 min. 4-Methyl-2-(methylthio)pyrimidine (2 g; 14.5 mmol) dissolved in THF (2 ml) is added dropwise and stirred for 30 mm at -78 C. 4-Fluoro-N-methoxy-N-methylbenzamide (2.66 g; 14.5 mmol) is dissolved in THF (3 ml) and added slowly to the reaction mixture. The mixture is warmed to r.t. within 45 min. and poured on water and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4 and evaporated to dryness to yield 2.5 g (65%) of yellow crystals after recrystallisation from tert.butyl methyl ether/hexane. 1H-NMR (200 MHz CDCl3): 3.00 (s, 3H): 6.30 (s, 1H); vinyl-H of enol); 7.00 (d, 1); 7.50 (dd, 2H); 8.20 (dd, 2H); 8.7 (d, 2H). Due to pH-dependent keto-enol tautomerism, signals may be duplicated.

According to the analysis of related databases, 116332-54-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Revesz, Laszlo; Schlapbach, Achim; US2002/49220; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 72080-83-2 as follows. Safety of Benzyl (2-aminoethyl)carbamate

General procedure: A mixture ofcompound 10 (0.15 g, 0.772 mmol), HOBt (0.23 g,1.70 mmol), EDCI (0.37 g, 1.93 mmol), benzoic acid(0.19 g, 1.54 mmol), and TEA (0.32 mL, 2.32 mmol) indry DMF (20 mL) was stirred at 80 C for 8 h. The mixturewas quenched with water (40 mL), then extracted withethyl acetate (3 x 40 mL). The combined organic layerextracts were washed with brine, dried over anhydrousMgSO4, filtered, and concentrated under reduced pressure.The residue was purified by flash column chromatography.The desired product was obtained as white solid (0.13 g,56.4 %).

According to the analysis of related databases, 72080-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abdel-Maksoud, Mohammed S.; El-Gamal, Mohammed I.; Gamal El-Din, Mahmoud M.; Kwak, Seong-Shin; Kim, Hyun-Il; Oh, Chang-Hyun; Medicinal Chemistry Research; vol. 25; 5; (2016); p. 824 – 833;,
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. 259796-12-8, name is 3,5-Dichloro-N-methoxy-N-methylbenzamide, A new synthetic method of this compound is introduced below., Safety of 3,5-Dichloro-N-methoxy-N-methylbenzamide

3,5-Dichloro-N-methoxy-N-methylbenzamide 12b (1.0 g, 4.27 mmol) was dissolved in 20 mL of dry tetrahydrogenEthylmagnesium chloride reagent (8.5 mL, 8.5 mmol, 1 M/THF) was added dropwise to furan at 0 C and allowed to react at room temperature for 2 hours. Add 20mLSaturate the ammonium chloride solution and quench the reaction. Extracted with ethyl acetate (825 mg, colorless oil), yield: 95.2%.

The synthetic route of 259796-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Haizheng Pharmaceutical Co., Ltd.; Guan Dongliang; Wang Zhongli; Bai Hua; Liu Zhubo; Meng Lichen; Zhao Weifeng; Ling Long; Wang Yan; (78 pag.)CN109574927; (2019); A;,
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. 337463-88-4, name is 6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

f) 6-Bromo-7-chloro-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (20g, 87.7 mmole) was dissolved inDMF (175 mL) and cooled in an ice bath. Chlorine gas was then slowly bubbled in for 45minutes, and then the saturated solution was stirred in the ice bath for 2 hours. Themixture was purged with nitrogen and slowly added with stirring to 1L of ice water whichcontained 10Og of Na2SO3, making sure to keep the temperature <15 C. After stirring 30minutes the product was filtered, washed thoroughly with water and dried to afford (22.5g,98%) of a white solid.1H NMR (400 MHz, DMSO-c/6): 4.76 (2H, s,), 7.78 (1H, s),11.71 (1H, s). 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; GLAXO GROUP LIMITED; WO2006/14580; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 120157-97-3, The chemical industry reduces the impact on the environment during synthesis 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, I believe this compound will play a more active role in future production and life.

To a solution of 4-BROMOPHENETHYLAMINE (10G, 48. 98mmol) in anhydrous DMF (150mL), containing anhydrous triethylamine (35mL, 244.9 mol), was added BOC2O. The reaction mixture was heated for 15 minutes at 50C. After cooling to room temperature, brine (100ML) and HCI (1N, 100ML) were added subsequently, and the mixture was extracted several times with ether. The recombined organic layer was washed again with brine, dried over sodium sulfate, filtered and evaporated. The crude was flashed with 10% ethyl acetate in hexanes to give the [2- (4-BROMO-PHENYL)-ETHYL]-CARBAMIC acid tert-butyl ester.’H NMR (CDCI3, 300MHZ) : 1.41 (s, 9H); 2.22 (t, J=7. 1HZ, 2H); 3.31 (m, 2H); 4.67 (s, broad, 1 H); 7.03 (d, J=8.2Hz, 2H); 7.38 (d, J=8.2Hz, 2H). A mixture of the above mentioned compound (1. 00g, 3. 33MMOL), 3, 4-DIMETHOXYPHENYLBORONIC acid (1. 21 G, 6. 66MMOL), and potassium hydroxide (2N, 5mL, 10MMOL) in THF (15mL) was degassed using argon for 5 minutes. Palladium tetrakis-triphenylphosphine (200mg, 0. 167MMOL) was added and the mixture was heated at 85C. After 24 hours, the reaction mixture was allowed to cool to room temperature. Brine (20mL) was added and the reaction mixture was extracted several times with ether. The recombined organic phase was extracted with brine, dried over sodium sulfate, filtered, and evaporated. Silica gel chromatography of the crude using 20% ethyl acetate/n-hexane afforded [2- (3′, 4′-DIMETHOXY-BIPHENYL-4YL)-ETHYLAMINE]-CARBAMIC acid tert-butyl ester as a white SOLID. 1H-NMR (CDCI3, 300MHZ) : 1.44 (s, 9H); 2.82 (t, J=6.9Hz, 2H); 3.39 (m, 2H); 3.91 (s, 3H); 3.93 (s, 3H); 4.67 (s, broad, 1H) ; 6.92 (d, J=8.2Hz, 1 H) ; 7.11 (m, 2H); 7.25 (m, 2H); 7.48 (d, J=8. 1 Hz, 2H). A solution of the above mentioned compound (1.14g, 3. 19mmol) in anhydrous methanol (50mL) was cooled in ice bath and then treated drop wise with acetyl chloride. Stirring was continued for 30 minutes at the same temperature followed by overnight stirring at room temperature. About 30mL of the solvent was removed by evaporation and the mixture was diluted with 200mL of ether. The entitled product was collected as a white solid by filtration, followed by washing with anhydrous ether and drying under high VACUUM.’H-NMR (D20, 300MHZ) : 2.80 (t, J=6.9Hz, 2H); 3.40 (m, 2H); 3.91 (s, 3H); 3.93 (s, 3H); 4.77 (s, broad, 1H) ; 7.00 (d, J=8.2Hz, 1H) ; 7.15 (m, 2H); 7.26 (m, 2H); 7.50 (d, J=8. 1HZ, 2H)

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-(4-Bromophenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOMEP INC.; WO2004/50620; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics