Month: March 2021

Reference of 14062-80-7,Some common heterocyclic compound, 14062-80-7, name is 4-Chloro-N,N-dimethylbenzamide, molecular formula is C9H10ClNO, 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.

N’-cyanobenzimidamide (16.8 g, 115 mmol),Compound A-2 (21 g, 115 mmol) and phosphorous oxychloride(12 mL, 128 mmol) was added to 500 mL of acetonitrile, followed by stirring and refluxing for 1 hour.After cooling to room temperature, the resulting solid was filtered,Washed with water and ethanol, and then dried to obtain CompoundA (27.6 g, yield 80%).

The synthetic route of 14062-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Kang Min-yeong; Park Tae-yun; Cho Seong-mi; Moon Jeong-uk; Jeong Min-u; Lee Jeong-ha; (29 pag.)KR2019/6353; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 14719-21-2, 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 14719-21-2 as follows.

F1 (0.7 mmol, 247 mg) was added to a single-necked flask and 9.7 mg CuI and 20.3 mg Pd (PPh3) 4 (tetrakistriphenylphosphine) palladium were weighed into a reaction flask. The reaction flask was evacuated, purged with nitrogen and wrapped in aluminum foil , 2.3 ml DMF was added,Stirring to dissolve, adding 0.2ml TEA, weighing F2 (254mg, 1.7mmol) dissolved in DMF was added to the above reaction flask, stirred at room temperature, the reaction overnight.TLC plate monitoring, EA as developing solvent, Rf = 0.35 as the raw material F1, Rf = 0.32 for the product F3, two very close position.After the reaction was over, the solvent was evaporated to dryness under reduced pressure and the residue was directly purified by column chromatography. Elution with 20: 1 DCM: MeOH as eluant gave 214 mg, yield 61%.

According to the analysis of related databases, 14719-21-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Jiao Tong University; Shen Yumei; Gong Bing; Shao Zhifeng; Zhao Xiaodong; Liu Yazhi; Li Xiaowei; Wu Xinyan; Wei Xiaofei; Tang Daonian; (99 pag.)CN104292117; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39549-79-6, name is 2-Amino-4-methylbenzamide, molecular formula is C8H10N2O, 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. category: amides-buliding-blocks

General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2mol%), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2¡Á5mL) and acetone (2¡Á5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39549-79-6, its application will become more common.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
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. 88-19-7, name is 2-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Formula: C7H9NO2S

{3-[2-methoxy-4-carboxy-benzyl]-1-methyl-1H-indol-5-yl}-carbamic acid cyclopentyl ester (7 kg), dimethyl amino pyridine (2.5 kg), dicyclohexyl carbodiimide (3.9 kg), and dichloromethane (70 L) are charged and stirred for about 15 minutes. O-toluene sulphonamide (3.4 kg) is added at 30 C. and the reaction solution is stirred for about 4 hours at 30 C. The unwanted separated solid is filtered and the reaction solution is washed with dichloromethane (2¡Á12 L). The obtained organic layer is washed with dilute hydrochloric acid and water and separated. The obtained organic solution is distilled off completely under vacuum below 45 C. Acetonitrile (14 L) is added and distilled off completely under vacuum. The obtained crude is cooled to 30 C., acetonitrile (35 L) is added and heated to 85 C., and stirred for about 40 minutes. The resultant reaction solution is cooled to 35 C. and stirred for about 55 minutes. The separated solid is filtered, washed with acetonitrile (7 mL), and suction dried for about 30 minutes. The obtained wet compound is again charged into a reactor containing methanol (84 L), heated to about 60 C., and stirred for about 30 minutes. The reaction solution is cooled to 30 C. and stirred for about 50 minutes for solid separation. The obtained solid is filtered, washed with methanol (7 L), and suction dried for 30 minutes. The solid is dried under vacuum at 70 C. for about 4 hours to afford the title compound.HPLC Purity: 97.5%

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; Anumula, Raghupathi Reddy; Gilla, Goverdhan; Alla, Sampath; Kurella, Sreenivasulu; Kopparapu, Janardana Sarma Ramachandra; Medisetti, Rama Krishna Venkata; Maddula, Srinivasula Reddy; US2009/149662; (2009); A1;,
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. 614-76-6, name is 2-BroMoacetanilide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 614-76-6

2-Bromoacetanilide (1 .68 g, 90% content, 7.06 mmol) is dissolved in dry THF (15 mL) and cooled to -78 C under a nitrogen atmosphere. n-Butyllithium (2.5 M solution in hexane, 5.93 mL, 14.8 mmol) is added dropwise and the mixture stirred at -78 C for 30 minutes. tert-Butyl 2-formylpropan-2-ylcarbamate (1 .39 g, 7.42 mmol) in dry THF (10 mL) is added dropwise and the mixture stirred for 30 minutes at -78 C then allowed to warm to -50 C over 1 hour. Saturated aqueous ammonium chloride solution (20 mL) is added, the mixture allowed to warm to room temperature and the phases separated. The organic phase is washed with brine, dried and the solvent removed. The residue is purified by flash chromatography (Eluent 0-2% MeOH in DCM) to give the title product (370 mg, 16%). UPLC-MS (Method 1 ): Rt = 1 .02 min MS (ESI+): m/z = 323 (M+H)+

According to the analysis of related databases, 614-76-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MAZZAFERRO, Rocco; FERRARA, Marco; GIOVANNINI, Riccardo; LINGARD, Iain; (195 pag.)WO2016/75239; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 94838-59-2,Some common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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 dihydro-2//-thiopyran-4(3//)-onc (0.488 g, 4.2 mmol), tert- butyl 4- aminophenethylcarbamate (0.5 g, 2.1 mmol) and ZnCh (0.859 g, 6.3 mmol) in methanol (10 mL) was stirred at room temperature overnight. After this time NaBHiCN (0.66 g, 10.5 mmol) was added and the mixture was heated at 40 C for 4 h. After it was cooled to room temperature, the reaction mixture was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified by column chromatography to afford the title compound as light-yellow solid (0.401 g, 56.7% yield). NMR (500 MHz, DMSO-r/d) d: 6.87 (d, J= 8.3 Hz, 2H), 6.79 (t, J = 5.3 Hz, 1H), 6.50 (d, J= 8.4 Hz, 2H), 5.31 (d, .7= 8.6 Hz, 1H), 3.26 – 3.19 (m, 1H), 3.03 (dd, J= 14.6, 6.3 Hz, 2H), 2.68 (dd, J= 9.6, 3.4 Hz, 4H), 2.52 (d, J= 9.6 Hz, 2H), 2.20 – 2.09 (m, 2H), 1.47 (ddd, J= 13.4, 9.7, 4.7 Hz, 2H), 1.37 (s, 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

Adding a certain compound to certain chemical reactions, such as: 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, 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 147356-78-3, COA of Formula: C6H11NO2

To a solution of N-methoxy-N-methyl-cyclopropanecarboxamide (1.2 g, 9.10 mmol) and [cis-2- bromo-7-deuterio-5-phenyl-5,6-dihydropyrrolo[l,2-b][l ,2,4]triazol-7-yl]oxy-tert-butyl-dimethyl- silane (1.8 g, 4.55 mmol) in tetrahydrofuran (40 mL) was added isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 6.83 mL, 13.66 mmol) dropwise at 0 C. The mixture was stirred at 0 C for 1.5 h and quenched by addition of saturated aqueous ammonium chloride (50 mL). The mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100 – 200 mesh, 0 to 20% ethyl acetate in petroleum ether) to give [cis-7-[tert- butyl(dimethyl)silyl]oxy-7-deuterio-5-phenyl-5,6-dihydropyrrolo[l,2-b] [l,2,4] triazol-2-yl]- cyclopropyl-methanone (450 mg, 26%>) as a colorless oil. LCMS RT = 1.030 min, m/z = 384.2 [M + H]+. LCMS (5 to 95%> acetonitrile in water + 0.03 %> trifluoacetic acid over 1.5 mins) retention time 1.030 min, ESI+ found [M+H] = 384.2.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of tert-Butyl (2-hydroxyethyl)(methyl)carbamate

To an ice-cooled solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (300mg, 1 .71 mmol)) in dry CH2CI2 (8.5ml_) under argon was added portion wise Dess-Martin periodinane (762mg, 1.8mmol). Once finished the addition, the reaction mixture was stirred at room temperature for 3h. The mixture was poured into saturated solutions of NaHCOs (50 mL) and Na2S203 (50 mL) and more CH2CI2 (100 mL). It was well-stirred at room temperature for 30 minutes. The organic phase was separated and washed with sat. aq. NaHC03 (1 x 20 mL). It was dried over magnesium sulphate and concentrated to afford the title compound (370 mg, 98%) as colourless oil together with a yellow solid, which was used in the next step without further purification.1H NMR (300 MHz, cdcl3) delta 9.61 (s, 1 H), 3.98 (d, J = 33.9 Hz, 2H), 2.94 (t, J = 10.8 Hz, 3H), 1 .46 (dd, J = 8.2, 6.3 Hz, 9H).

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 57561-39-4.

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; GUAL ROIG, Silvia; PRAT QUINONES, Maria; PUIG DURAN, Carlos; WO2013/68552; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 3984-14-3, 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. 3984-14-3, name is N,N-Dimethylsulfamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 16; Preparation of Compound 16: N-(4,6-dimethyl-2-pyridinyl)valyl-(4R)-N-((1R,2S)-1-((dimethylsulfamoyl)carbamoyl)-2-vinylcyclopropyl)-4-((6-methoxy-1-isoquinolinyl)oxy)-L-prolinamide; Step 1:; To a solution of N-Boc-vinylcyclopropane carboxylic acid (1.83 g, 8.05 mmol) and THF (32 mL) was added 1,1′-carbonyldiimidazole (1.44 g, 8.86 mmol). After stirring at room temperature for 3 hours, the reaction mixture was treated with N,N-dimethylsulfamide (1.0 g, 8.05 mmol) followed by DBU (2.45 g, 16.1 mmol) and was stirred at room temperature for an additional 15 hours. The reaction was then diluted with ethyl acetate (50 mL) and washed with 1.0M aqueous HCl (2¡Á25 mL). The aqueous layer was extracted with ethyl acetate (2¡Á50 mL). The combined organic portion was washed with H2O (25 mL) and brine, dried over MgSO4, filtered, and concentrated to a light yellow solid (2.6 g, 97% yield) which was used without further purification. LC-MS, MS m/z 356 (M++Na).

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,N-Dimethylsulfamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, 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 456-64-4, HPLC of Formula: C7H6F3NO2S

Intermediate 7 (3 g) was dissolved in dimethylformamide (100 mL) and the solution cooled to 0C under nitrogen. Triethylamine (2.3 mL) was added and the stirred solution treated with N-phenyltrifluoromethanesulfonamide (4.83 g). After 30 minutes at 0C the reaction mixture was allowed to reach room temperature and stirred for 72 hours. The reaction mixture was diluted with water (5 ml) and concentrated, treated with water (200 ml) and extracted with ethyl acetate (4x 250 ml). The combined organic extracts were washed with water (2x 250 mL), dried (Na2SO4), filtered, concentrated to dryness and purified by silica gel chromatography, eluting with ethyl acetate/cyclohexane (5:95, 10:90 then 20:80, v/v) to give the title compound.MS calcd for (C30H30F3NO7S + H)+: 620 MS found (electrospray): (M+H)+= 620

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, 1,1,1-Trifluoro-N-phenylmethanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/96774; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics