Month: February 2021

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 54616-47-6 as follows. category: amides-buliding-blocks

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

According to the analysis of related databases, 54616-47-6, the application of this compound in the production field has become more and more popular.

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: 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, 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 147751-16-4, Recommanded Product: tert-Butyl methylsulfonylcarbamate

N-{l-[(lS,3R)-3-(2,2,2-Trifluoro-ethylamino)-cyclopentyl]-lH-imidazo[4,5-c]quinolin-2- ylmethyl} -methanesulfonamideN-tert-Butylcarbamate-N-{l-[(lS,3R)-3-(2,2,2-trifluoro-ethylamino)-cyclopentyl]-lH- imidazo[4,5-c]quinolin-2-ylmethyl} -methanesulfonamide A suspension of {l-[(lS,3R)-3-(2,2,2-trifluoro-ethylamino)-cyclopentyl]-lH-imidazo[4,5- c]quinolin-2-yl} -methanol (139 mg, 0.38 mmol) in anhydrous THF (3.8 mL), under an atmosphere of nitrogen was treated with tert-butyl N-methanesulfonylcarbamate (164 mg, 0.84 mmol), followed by triphenylphosphine (200 mg, 0.76 mmol) and then diisopropyl azodicarboxylate (150 mu?, 0.76 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc and water and the phases separated. The aqueous layer was extracted with EtOAc (2x) and the combined organic phases washed (brine), dried (sodium sulfate) and concentrated in vacuo to afford 780 mg of a yellow oil. Purification by column chromatography on an Isolute SCX-2 cartridge (eluting with MeOH and then 2M NH3 in MeOH) afforded 192 mg of a golden glassy solid. This was purified by filtration through a pad of silica gel (gradient: 0 to 2% [2M NH3 in MeOH] in EtOAc) to afford 169 mg (82%) of N-tert-butylcarbamate-N- { 1 – [( 1 S ,3R)-3 -(2,2,2-trifluoro-ethylamino)-cyclopentyl] – 1 H- imidazo[4,5-c]quinolin-2-ylmethyl}-methanesulfonamide as a colourless gum. LCMS (Method B, ESI): RT = 2.67 min, m+H = 542.0; 1H NMR (400 MHz, CDC13): delta 9.20 (s, 1 H), 8.40 (d, 1 H), 8.28 (d, 1 H), 7.66 (m, 2 H), 5.54-5.30 (m, 3 H), 3.68 (s, 3 H), 3.60 (m, 1 H), 3.30 (m, 2 H), 2.60 (m, 2 H), 2.33 (m, 1 H), 2.15 (m, 2 H), 1.98 (m, 1 H), 1.50 (s, 9 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; F. HOFFMANN-LA ROCHE AG; HURLEY, Christopher; KULAGOWSKI, Janusz; ZAK, Mark; WO2013/7768; (2013); 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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below., Product Details of 16066-84-5

Description 84; 1,1-Dimethylethyl (6-formyl-3-pyridinyl)methylcarbamate (D84); A mixture of 5-bromo-2-pyridinecarbaldehyde (1.5 g, 8.064 mmol), 1 ,1-dimethylethyl methylcarbamate (D83) (1.267 g, 9.677 mmol), tris(dibenzylideneacetone) dipalladium(O) (0.148 g, 0.161mmol), xantphos (0,373 g, 0.645 mmol) and cesium carbonate (3.678 g, 11.289 mmol) in dioxane (35 mL) was heated at 11O0C overnight under an argon atmosphere. On cooling, the solvent was removed in vacuo and the residue partitioned between EtOAc and water. The organic layer was separated, washed with water and brine, dried and concentrated to give the crude product which was purified by column chromatography. Elution with 0-50% ether/petroleum ether gave the title compound as a brown oil (0.977 g). deltaH (CDCI3, 400MHz) 10.01 (1 H, s), 8.79 (1 H, d), 7.94 (1 H, d), 7.86 (1 H, dd), 3.40 (3H, s), 1.53 (9H, s). MS (ES+): 259.1 (MNa+), 181.2, no molecular ion (MH+) observed.

The synthetic route of 16066-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/729; (2008); 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. 78191-00-1, name is N-Methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H9NO2

Intermediate 8: To a solution of 5-methylthiazole (0.179 mL, 2.017 mmol) in ether (13.63 mL) was added nBuLi (1.387 mL, 2.219 mmol, 1.6 M in hexanes) dropwise at -78 C and the reaction mixture was stirred at this temperature for 15 mm. A solution of N-methoxy-N-methylacetamide (229 mg, 2.2 19 mmol) in THF (4.0 mL) was addeddropwise and the reaction mixture warmed to rt and stirred for 1 h. The reaction mixture was quenched with sat. NH4C1. The organic layer was separated and washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by chromatography to yield Intermediate 8 (123 mg, 0.87 1 mmol, 43.2% yield) as a pale yellow solid. ?H NMR (500 MHz, CDC13) oe 7.66 (s, 1H), 2.68 (s, 3H), 2.57 (s,3H). LCMS Anal. Calc?d for C6H7NOS 141.0, found [M+H] 141.9.

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 78191-00-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MENG, Wei; ZHAO, Guohua; WO2015/134701; (2015); 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. 7341-96-0, name is Propiolamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 7341-96-0

The imine (0.2mmol), rhodium acetate (0.002mmol), Molecular sieve (300 mg) and the mixture is dissolved 1.5 ml dichloromethane solvent, into mixed solution 1, in 20 C stirring for 10 minutes. Then the propargyl amide (0.24mmol) and methoxyphenyl diazo acetic acid methyl ester (0.24mmol) dissolved in 1.0 ml methylene chloride solvent, into solution 2. The solution 2 for 20 C lower, in 1 hour for adding and mixing the solution in the injection pump 1. The reaction mixture is purified by rapid column chromatography, to obtain the pure product, its structure is formula (d) is shown. The yield is 81%, dr value equal to 90:10. The product of the1As shown in Figure 7, H NMR schematic view thereof13C NMR schematic view as shown in Figure 8.

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 7341-96-0.

Reference:
Patent; EAST CHINA NORMAL UNIVERSITY; HU, WENHAO; WU, YONG; WANG, WENKE; TANG, MIN; (29 pag.)CN106146334; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 51-06-9,Some common heterocyclic compound, 51-06-9, name is 4-Amino-N-(2-diethylaminoethyl)benzamide, molecular formula is C13H21N3O, 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.

EXAMPLE V 4-[(Butylsulfonyl)amino]-N-[2-(diethylamino)ethyl]benzamide hydrobromide To 100 ml of methylene chloride add 6.52 g (36.2 mmole) of 4-amino-N-[2-(diethylamino)ethyl]benzamide and cool to -78 C. under nitrogen atmosphere. To this solution slowly add 5.61 g (36.2 mmole) of n-butanesulfonyl chloride. When the addition is complete, allow the reaction mixture to warm to room temperature and monitor by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). Upon completion of the reaction remove the solvent in vacuo. To the resulting oil add 50 ml H2 O followed by 50% sodium hydroxide until pH=14. Extract the aqueous layer with 3*50 ml diethyl ether and 2*25 ml of methylene chloride. To the aqueous layer add concentrated HCl to bring the pH to 8.5. Extract the aqueous solution with 3*75 ml of methylene chloride. Combine the extracts and dry over sodium sulfate. Filter the drying agent and remove the solvent in vacuo. Dissolve the resulting oil in acetonitrile. Bubble HBr gas through the solution until pH=1. Remove the solvent in vacuo. Triterate the resulting oil in diethyl ether and ethyl acetate to yield a precipitate. Isolate by filtration and recrystallize from MeOH/ethyl acetate to afford the title compound. NMR (DMSO-d6): delta=0.82(t,3), 1.22(t,6), 1.34(m,2), 1.63 (m,2), 3.23(m,8), 3.57(m,2), 7.26 (d,2), 8.67(t,1), 9.22(br s,1) and 10.19(s,1)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-N-(2-diethylaminoethyl)benzamide, its application will become more common.

Reference:
Patent; Schering A.G.; US4629739; (1986); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7326-73-0, name is 3-(N,N-Dimethylsulfamoyl)benzoic acid, 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: 3-(N,N-Dimethylsulfamoyl)benzoic acid

To a solution of 3-(dimethylsulfamoyl)benzoic acid (38.30 mg, 167.06 gmol) in DCM (1 .0 ml_) were added HATU (69.87 mg, 183.76 gmol), DIEA (64.77 mg, 501 .18 gmol, 87.30 gl_) and intermediate i- 45b (100 mg, 167.06 gmol). The reaction mixture was stirred at 20 C for 12 hours and then poured into water (2.0 ml_). The solution was extracted with EtOAc (2.0 ml_ * 3). The combined organic extracts were washed with brine (5.0 ml_), dried over Na2SC>4 and filtered. The filtrate was concentrated to give a residue. The residue was purified by column chromatography (S1O2. PE/EA=50/1 -1 /1 ) to give intermediate i-45c as a white solid. LCMS (ESI) m/z: [M+H]+ = 696.0 Chiral HPLC: OJ-3-MeOH(DEA)-60-7MIN-3ML-35T, 5.276min.

The synthetic route of 7326-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ANTHONY, Neville, John; MILLAN, David, Simon; VASWANI, Rishi, G.; SCHILLER, Shawn, E.R.; (239 pag.)WO2019/152437; (2019); 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. 5202-85-7, name is 2-Amino-5-chlorobenzamide, A new synthetic method of this compound is introduced below., Safety of 2-Amino-5-chlorobenzamide

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.

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:
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

Synthetic Route of 2675-89-0, 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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of (4aR,4bS,6aS,9aS,9bR)-4a,6a-dimethyl-4,4a,4b,5,6,6a,9,9a,9b,10-decahydro-1H-indeno[5,4-f]quinoline-2,7(3H,8H)-dione (794 mg, 2.7 mmol) in anhydrous DMF (30 mL) was added NaH (60%, 324 mg, 8.1 mmol) and 2-chloro-N,N-dimethylacetamide (670 mg, 5.5 mmol) at 0 C., then the reaction was stirred under 50 C. for 2 hour. Then cooled down to room temperature and partitioned between ethyl acetate (20 mL) and water (20 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (25 mL¡Á3). The combined organic layers were dried over Na2 SO4. After filtration, the organic phase was concentrated under vacuum to afford 2-((4aR,4bS,6aS,9aS,9bR)-4a,6a-dimethyl-2,7-dioxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydroindeno[5,4-f]quinolin-1-yl)-N,N-dimethylacetamide as a yellow solid (760 mg, yield 74%). 1H-NMR (400 MHz, CDCl3): 4.82 (m, 1H), 4.15 (m, 1H), 3.06 (s, 3H), 2.97 (m, 3H), 2.50 (m, 3H), 2.25 (m, 1H), 2.14 (m, 1H), 1.19 (m, 12H), 1.15 (s, 3H), 0.90 (s, 3H). LC-MS (m/z) 373 [M+H]+.

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

Reference:
Patent; LEAD THERAPEUTICS, INC.; US2010/105700; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16313-66-9, A common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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: A dry 50 mL flask was charged with 2-aminobenzamides 1 (1.1 mmol), 5,5-dimethyl-1,3-cyclohexanedione 2 (0.280 g, 1.0 mmol), iodine (0.026 g, 0.01 mmol) and toluene (10.0 mL). The mixture was stirred at 80 C until the reactant 1 was consumed. After the completion of the reaction monitored by TLC, toluene was recovered by distillation under reduced pressure, and the residue was purified by silica column chromatography using ethyl acetate and petroleum ether (1:3) as the eluent to give products 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:
Article; Lu, Lian; Zhang, Mei-Mei; Jiang, Hong; Wang, Xiang-Shan; Tetrahedron Letters; vol. 54; 8; (2013); p. 757 – 760;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics