Month: August 2021

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. 711007-44-2, name is 2,3-Diaminobenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2,3-Diaminobenzamide

General procedure: In a dark environment, a mixture of 2,3-diaminobenzamide(1.51 g, 10 mmol), PYTZ (20 mg), and ethanol (200 mL)was taken in an open pear-shaped bottle, stirred magneticallyat room temperature, and then aldehyde (10 mmol) wasadded slowly in 2 min. The bottle was exposed to visiblelight (Xenon, 10 A) under stirring condition. The reactionwas monitored by TLC. After the reaction completed, thereaction mixture was transferred to a three-neck bottle outsideof the photochemical reactor and air was introduced toensure that the intermediate was completely oxidized. Then,the solvent was evaporated in vacuum to 40 mL until thesolid appeared. The mixture was cooled down in an ice bathfor crystallization, filtration. The crude solid was recrystallizedfrom 25 mL ethanol (30 C) to get the target products.

The synthetic route of 711007-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Li-Jie; Yang, Kang; Li, Chun-Yu; Sun, Ya-Quan; Chemical Papers; vol. 73; 11; (2019); p. 2697 – 2705;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 49805-30-3,Some common heterocyclic compound, 49805-30-3, name is 2-Azabicyclo[2.2.1]hept-5-en-3-one, molecular formula is C6H7NO, 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) (1S,4R)-tert-Butyl 3-oxo-2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylate (+)-2-Azabicyclo[2.2.1]hept-5-en-3-one (Chiroscience, Cambridge, England; 54.565 g, 0.500 mole) was dissolved in dry tetrahydrofuran (350 mL). Di-tert-butyl carbonate (Aldrich, 114.87 g, 0.510 mole as 97%) and 4-dimethylaminopyridine (Aldrich, 600 mg) were added to the stirred mixture. The resulting solution was stirred at ambient temperature for 2 hours. Solvent was evaporated under reduced pressure and the residual orange solid was crystallized from toluene-hexanes to give title compound as white crystals (95.72 g, 91%), m.p. 85-86 C.; 1H-NMR (CDCl3) delta: 1.50 (s, 9H), 2.24 (app AB q, J=8.4 Hz, 2H), 3.39 (br s, 1H), 4.96 (m, 1H), 6.66 (m, 1H), 6.89 (m, 1H). Anal. Calcd. For C11H15NO3: C, 63.14; H, 7.21; N, 6.69. Found: C, 63.20; H, 7.26; N, 6.65.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Azabicyclo[2.2.1]hept-5-en-3-one, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6630477; (2003); B1;,
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. 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of tert-Butyl 3-aminobenzylcarbamate

EXAMPLE 5A; A mixture of EXAMPLE 1B (1 0 g), tert-butyl 3-aminobenzylcarbamate (1 373 g), HATU (2.348 g) and TEA (2.347 mL) in DMF (30 mL) was stirred at room temperature for 24 hours, then diluted with water and extracted with ethyl acetate The ethyl acetate phase was washed (brine), dried (MgSO4) and filtered The filtrate was evaporated to dryness to leave an oil which was triturated with water The resulting precipitate was filtered and dried

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 147291-66-5.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/12312; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)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 389890-43-1, Recommanded Product: tert-Butyl (cis-3-hydroxycyclobutyl)carbamate

General procedure: To a solution of (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3- methyl-1H-pyrazolo[3,4-d]pyrimidine (435b) (150 mg, 0.39 mmol), triphenylphosphine (206 mg, 0.79 mmol), tert-butyl cis-4-hydroxycyclohexylcarbamate (127 mg, 0.59 mmol) in THF (3 mL) at 0 C was added dropwise DIAD (0.12 mL, 0.59 mmol). The reaction mixture was stirred at RT overnight, concentrated in vacuum and the residue obtained was purified by flash column chromatography [silica (12 g), eluting with EtOAc in hexane from 0-60%] to furnish tert-butyl ((tra5)-4-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-l-yl)- 6-chloro-3-methyl-lH-pyrazolo[3,4-d]pyrimidin-l-yl)cyclohexyl)carbamate (435c) (150 mg, 66 % yield) as a white solid;1H MR (300 MHz, DMSO-d) delta 6.83 (d, J = 7.9 Hz, 1H), 4.54 – 4.38 (m, 2H), 3.90 – 3.63 (m, 4H), 3.32 – 3.22 (m, 1H), 2.55 (s, 3H), 2.13 – 1.75 (m, 10H), 1.39 (s, 1 1H), 0.82 (s, 9H), -0.05 (s, 6H); MS (ES+): 579.3 (M+l).

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 (cis-3-hydroxycyclobutyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 1943-79-9,Some common heterocyclic compound, 1943-79-9, name is Phenyl methylcarbamate, molecular formula is C8H9NO2, 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.

Phenyl N-methylcarbamate (350 mg, Production example 2-1) was added to a solution of 4-(3-methyl-1H-5-indolyl)oxy-2-pyridinamine (500 mg), sodium hydride (93 mg) and N,N-dimethylformamide (5 ml) at room temperature; and the reaction mixture was stirred for 2 hours and 45 minutes. Water was added to the reaction mixture; extraction was performed with ethyl acetate; and purification was performed by NH-silica gel column chromatography (Fuji Silysia, hexane: ethyl acetate = 1: 2, sequentially, ethyl acetate) to yield the title compound as a pale yellow amorphous solid (365 mg). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 2.19 (3H, s), 2.80 (3H, d, J=4.0 Hz), 5.73 (1H, d, J=2.4 Hz), 5.83 (2H, s), 6.12 (1H, dd, J=5.6, 2.4 Hz), 7.00 (1H, dd, J=8.8, 2.4 Hz), 7.27 (1H, d, J= 2.4 Hz), 7.64 (1H, s), 7.75 (1H, d, J=5.6 Hz), 7.98 (1H, q, J=4.0 Hz), 8.24 (1H, d, J=8.8 Hz).

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

Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 1195768-19-4, 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 1195768-19-4 as follows.

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, l.OlmL, l.Olmmol) was added to a cooled (0C) solution of Methyl 3-((2,6-difluorophenyl)sulfonamido)-2- fluorobenzoate (lOOmg, 0.29mmol) in THF (2.5mL). After lOmin of stirring, a solution of 4-Methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (76mg, 0.29mmol) in THF (lmL) was slowly added and the reaction mixture was allowed to warm to room temperature. After 2 hours of stirring, saturated aqueous ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (two times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure to afford the title compound (170mg, quant) as a mixture of ketone and enol. LC/MS (ES+): 577.4 (M+l).

According to the analysis of related databases, 1195768-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 127828-22-2, 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 127828-22-2 as follows.

General procedure: To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and Dasatinib- COOH (50 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 0.1 mmol, 1 eq) and DIPEA (48 mL) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the reside was dissolved in DCM (1 mL) and treated with a solution of anhydrous HC1 in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid.

According to the analysis of related databases, 127828-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF DUNDEE; CIULLI, Alessio; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; (183 pag.)WO2019/238816; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 52898-49-4, name is N,4-Dimethoxy-N-methylbenzamide, 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 52898-49-4, name: N,4-Dimethoxy-N-methylbenzamide

General procedure: In a helium-filled glove box, the desired number ofequivalents of Na-AG or Na-SG were added to a round bottom flask, along with aglass-coated stir bar, and the flask sealed with a septum. This closed systemwas then taken out of the glove box, continuously purged with nitrogen, followedby injection of the pure synthesized Weinreb amide dissolved in THF. The resulting mixture was stirred for thetime specified. After completion of the reaction, the mixture was then partitioned using ethyl acetate and brine. The organic layer was concentrated under reducedpressure using a rotary evaporator. 1H NMR of the crude product wastaken to check for reaction extent/completion and to identify the productsobtained. Crude product was fractionated and purified by columnchromatography on silica gel to afford the desired product and byproducts.

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,4-Dimethoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jackson, James E.; O’Brien, Brittany N.; Kedzior, Sonya K.; Fryz, Gage R.; Jalloh, Fatmata S.; Banisafar, Arash; Caldwell, Michael A.; Braun, Max B.; Dunyak, Bryan M.; Dye, James L.; Tetrahedron Letters; vol. 56; 45; (2015); p. 6227 – 6230;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 88-96-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 88-96-0 name is Phthalamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

1) Synthesis of phthalimide potassium A round-bottom flask containing 3200 mL dehydrated alcohol was added with 160.0 g phthalamide, and heated and refluxed for 0.5 h, until only a small amount of raw materials was not dissolved. The resulted hot solution was added into 61.0 g potassium hydroxide solution (including 60 mL water and 180 mL alcohol) by decantation, by which a white precipitate was formed immediately. Then the solution was cooled and filtered to obtain filtered residue, and alcohol was recycled. The filtered residue was washed with 400 mL acetone, 196.0 g phthalimide potassium was obtained, and the yield was 98.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Phthalamide, and friends who are interested can also refer to it.

Reference:
Patent; Institue of Transfusion Medicine, Academy of Military Medical Sciences, People’s Liberation Army of China; PEI, Xuetao; LI, Yanhua; WANG, Sihan; ZHANG, Jing; YAO, Hailei; SHI, Wei; YUE, Wen; EP2949323; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 713-41-7, name is 2-Amino-4-(trifluoromethyl)benzamide, 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 713-41-7, Quality Control of 2-Amino-4-(trifluoromethyl)benzamide

Production Example 3 (1) 0753] A mixture of 1.0 g of 2-amino-4-trifluromethylbenzamide, 813 mg of 2-ethylsulfanylbenzaldehyde, 764 mg of sodium bisulfite and 4 ml of DMA was stirred at 150C for 8 hours. A saturated aqueous sodium bicarbonate solution and water were added to the cooled reaction mixture, and the precipitated solid was filtered. The resulting solid was washed with water and n-hexane and then dried to obtain 1.49 g of 2-(2-ethylsulfanylphenyl)-7-trifluoromethyl-3H-quinazolin-4 -one. 2-(2-Ethylsulfanylphenyl)-7-trifluoromethyl-3H-quinaz olin-4-one [0754] 1H-NMR(CDCl3)delta: 10.46(1H, brs), 8.43(1H, d), 8.11(1H, s), 7.91(1H, dd),7.72(1H, dd), 7.54 (1H, dd),7.50(1H, td), 7.41(1H, td), 2.92(2H, q), 1.28(3H, t).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-(trifluoromethyl)benzamide, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; TAKAHASHI, Masaki; ITO, Mai; NOKURA, Yoshihiko; TANABE, Takamasa; SHIMIZU, Chie; EP2865671; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics