Category: amides-buliding-blocks

Application of 830-43-3, These common heterocyclic compound, 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, 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 the same manner as in Example 158, 0.390 g of 1-(2-chlorobenzyl)-2-methyl-6-[4-(trifluoromethyl)benzenesulfonylcarbamoyl]benzimidazole (221) were formed from 0.45 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole, 0.486 g of N,N’-carbonyldiimidazole, 0.676 g of 4-(trifluoromethyl)benzenesulfonamide and 0.457 g of diazabicycloundecene. Properties of Compound (221): 1H-NMR(DMSO-d6, delta): 2.52(3H, s), 5.62(2H, s), 6.47(1H, d, J=7.2 Hz), 7.22(1H, t, J=7.5 Hz), 7.34(1H, t), 7.56(1H, d, H=8.0 Hz), 7.66(1H, d, 8.5 Hz), 7.78(1H, d), 7.97(2H, d, J=8.3 Hz), 8.06(1H, s), 8.15(2H, d, J=8.3 Hz). IR(KBr): 1620 cm-1. Mass(FAB): m/e 508(M+1). mp: 288.0-292.0 C.

Statistics shows that 4-(Trifluoromethyl)benzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 830-43-3.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6352985; (2002); B1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, 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 25625-57-4, Formula: C9H7BrF3NO

Tert-butyl 2-AMINOETHYLCARBAMATE (0.32 g, 2 mmol) was dissolved in dichloromethane with DIEA (0.6 mL, 3.4 mmol). To this solution, 2-BROMO-N- (3- (TRIFLUOROMETHYL)- phenyl) acetamide was added and the reaction mixture stirred for 6 hours at room temperature. The reaction mixture was concentrated to an oil and purified by column chromatography (eluent: ETOAC) to give the product 0.37 g, 1.02 mmol, 50% YIELD.1H NMR (500 MHz, CDCl3) 5 9.39 (s, 1H), 7.82 (s, 1H), 7.78 (d, J = 7.8 Hz, 1H), 7.37 (t, J = 7.9 Hz, 1H), 7.28 (d, J = 7.8 Hz, 1H), 4.68 (s, 1H), 3.36 (s, 2H), 3.22 (dd, J = 11. 2,5. 5 Hz, 2H), 2.74 (t, J= 5. 7 HZ, 2H).

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; VERTEX PHARMACEUTICALS INCORPORATED; WO2005/19190; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 94838-59-2, A common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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.

To a solution of tert-butyl 2-(4-aminophenyl)ethylcarbamate (200 mg, 0.85 mmol) in Toluene (2 mL) was added N,N-dimethylformamide azine (120 mg, 0.85 mmol, prepared by the method described in Bioorg. Med. Chem. Letters, 6(15): 1825-1830, 1996) and TsOH.H2O (16 mg, 0.08 mmol). Resulting solution was heated to reflux and stirred overnight. Reaction mixture was cooled, concentrated in vacuo, and subjected to silica gel chromatography eluting with 2%-5% MeOH in CH2Cl2 to give 250 mg (100%) tert-butyl 2-[4-(4H-1,2,4-triazol-4-yl)phenyl]ethyl-carbamate. LCMS (ES) 289.3 m/z (M+H)+.

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; Su, Dai-Shi; Bock, Mark G.; US2005/20591; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 89976-75-0, 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. 89976-75-0, name is 6-Amino-2H-1,4-benzoxazin-3(4H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

45.iii) 6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-oneTo a solution of tert-butyl-dimethyl-((S)-1-oxiranylmethoxy)-silane (commercial; 13.0 g, 69 mmol) in MeCN (220 mL) was added LiClO4 (22 g, 207 mmol). 6-Amino-4H-benzo[1,4]oxazin-3-one (commercial; 11.45 g, 64 mmol) was added and the mixture was stirred at 50¡ã C. for 6 h. The solvent was removed in vacuo and the residue was purified by CC (DCM/MeOH/NH4OH 1000/25/2->1000/100/2) to afford the title compound as a pale brown foam (11.16 g, 44percent).(ESI, m/z): 353.3 [M+H+].

The synthetic route of 6-Amino-2H-1,4-benzoxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Actelion Pharmaceuticals Ltd; US2011/39823; (2011); 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 147751-16-4 as follows. name: tert-Butyl methylsulfonylcarbamate

1.6 M n-Butyl lithium in hexanes (20.2 ml, 32.4 mmol) was added drop wise to a solution of N,N-diisopropylethylamine (5.91 ml, 33.9 mmol) in 25 ml dry THF in ice bath and stirred for 30 minutes. Then tert-butyl methylsulfonylcarbamate in 25 ml dry THF was added slowly and stirred at 0 C. for 1 hour. The mixture was then cooled to -78 C. and 4-phenoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (3.01 g, 15.4 mmol) in 25 ml dry THF was added slowly. The reaction was slowly warmed up to room temperature and stirred at room temperature for 1 hour. Then it was quenched with water, acidified with 1N HCl to pH 3, extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, filtered and concentrated. Column purification gave 1 g product as off-white solid. 1H NMR (DMSO-d6, 300 MHz) delta ppm 11.34 (s, 1H), 9.39 (s, 1H), 7.54 (d, J=8.10 Hz, 1H), 7.42-7.37 (m, 2H), 7.28 (d, J=2.40, 1H), 7.22-7.12 (m, 2H), 7.03-7.01 (m, 2H), 5.43 (dd, J=9.3, 1.8 Hz, 1H), 4.01 (dd, J=13.5, 2.1 Hz, 1H), 3.54 (dd, J=14.7, 9.3 Hz, 1H), 1.42 (s, 9H). MS (ESI) m/z 418 [M-H]-.

According to the analysis of related databases, 147751-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; GlaxoSmithKline; US2010/256092; (2010); 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. 6228-73-5, name is Cyclopropanecarboxamide, A new synthetic method of this compound is introduced below., Computed Properties of C4H7NO

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4- c]pyridine (60 mg, 0.17 mmol), cyclopropanecarboxamide (0.019 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos (0.017 g, 0.034 mmol) and Cs2C03 (0.11 g, 0.34 mmol) in dioxane (3 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160 C for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified by reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HC03 to give the desired product as a white solid (13 mg, 21% yield). l NMR (500 MHz, DMSO- 6): delta 11.44 (s, 1H), 8.46 (d, J= 6.0 Hz, 1H), 7.92 (d, J= 6.0 Hz, 1H), 7.72-7.67(m, 3H), 2.09-2.06 (m, 1H), 0.9-0.87 (m, 4H). LCMS (Method A): RT = 5.84 min, m/z: 371.0 [M+H+].

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; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 402-46-0, Recommanded Product: 4-Fluorobenzenesulfonamide

General procedure: To a round-bottom flask (100 mL) that contained a solution of aryl sulfonamide (5 mmol), DMAP (5 mmol), and EDCI, (5mmol) in CH2Cl2 (50 mL) was added the synthesized cinnamic acid 5-7 (5 mmol) at room temperature. The resulting mixture was stirred at room temperature for overnight, then cooled to 5 , and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 ¡Á 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (5a-7e). Crystallographical and experimental data of compounds 5b and 6c were summarized in Table 3.

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, 4-Fluorobenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Luo, Yin; Zhou, Yang; Song, Yanhua; Chen, Guo; Wang, Yu-Xiang; Tian, Ye; Fan, Wei-Wei; Yang, Yu-Shun; Cheng, Tao; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3634 – 3638;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121-30-2, 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 121-30-2 as follows.

To the product of Example 74a (1.63 g, 10 mmol) and 2-amino-6-chloro-1,3-benzenedisulfonamide (Aldrich Chemical Co.,1.439 g, 5 mmol) in anhydrous dioxane (50 mL) was added Amberlyst (15) wet strongly acidic resin (3 g). The reaction mixture was stirred gently at room temperature for 2 days, then decanted into another flask. The resin was washed with dioxane (2 mL) and the washings added to the reaction mixture. Fresh Amberlyst (15) wet strongly acidic resin (2 g) was added to the reaction mixture and the stirring was continued at room temperature for 24 hours. The resin was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was treated with ethyl acetate and washed with saturated aqueous sodium carbonate, water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by column chromatography over silica gel, eluting with 3% methanol in dichloromethane gave 1.3 g of an oil that was triturated with 20% ethyl acetate in hexane to give the title compound (1.1 g, 54% yield) as a white solid: mp 113-117 C.; 1H NMR (d6-DMSO) delta 8.03 (s, 1H), 8.01 (s, 1H), 7.97 (s, 1H), 7.52 (s, 2H), 6.98 (s, 1H), 4.96-4.89 (m, 1H), 4.77-4.65 (m, 2H), 2.28-2.15 (m, 2H); 13C NMR (d6-DMSO) delta 146.3, 134.2, 128.6, 125.4, 118.2, 117.1, 69.1, 63.3, 30.4. Mass spectrum (API-TIS) m/z 404 (MH)+, 406 (MH+2)+.

According to the analysis of related databases, 121-30-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); 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 35303-76-5 as follows. COA of Formula: C8H12N2O2S

Step 4. (S)-tert-butyl 6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-2-(3-((S)-1-tert-butoxy-1,5-dioxo-5-(4-sulfamoylphenethylamino)pentan-2-yl)ureido)hexanoate A solution of (S)-4-(3-((S)-6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-1-tert-butoxy-1-oxohexan-2-yl)ureido)-5-tert-butoxy-5-oxopentanoic acid (80 mg, 0.098 mmol), 4-(2-aminoethyl)benzenesulfonamide (30 mg, 0.15 mmol), 2-(1-H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU, 50 mg, 0.17 mmol), and DIPEA (0.50 mL) in DMF (5 mL) was stirred at 40 ¡ãC overnight. The solvents were evaporated under reduced pressure to give a residue, which was purified by Biotage SP4 using a gradient of 0-20percent MeOH in DCM to give (S)-tert-butyl 6-(bis((1-(2-tet¡ãt-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-2-(3-((S)-1-tert-butoxy-1,5-dioxo-5-(4-sulfamoylphenethylamino)pentan-2-yl)ureido)hexanoate (100 mg, 100percent). ESMS m/z: 501.9 (M/2+H)+.

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Molecular Insight Pharmaceuticals, Inc.; Babich, John W.; Zimmerman, Craig N.; Joyal, John; Maresca, Kevin P.; Marquis, John; Lu, Genliang; Wang, Jian-cheng; Hillier, Shawn; (110 pag.)EP2706057; (2016); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 15441-10-8, name is 3-(Aminosulfonyl)propanoic acid, 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. name: 3-(Aminosulfonyl)propanoic acid

General procedure: To a solution of 3-(4-((2-aminopropyl)thio)-1 ,2,5-oxadiazol-3-yl)-4-(3-(difluoromethyl)-4- fluorophenyl)-1 ,2,4-oxadiazol-5(4H)-one hydroiodide (Int 102) (416 mg, 0.81 mmol), HATU (462 mg, 1 .22 mmol) and Et3N (245 mg, 2.43 mmol) in DMF (8 mL) 2- sulfamoylacetic acid (135 mg, 0.97 mmol) was added and the mixture was stirred at rt overnight. EtOAc (20 mL) was added and the mixture was extracted with water (2 x 20 mL). The combined organic layers were dried over anhydrous Na2S0 , filtered and concentrated to dryness. The residue was purified by column chromatography to give the title compound as a white solid.

The synthetic route of 3-(Aminosulfonyl)propanoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX DISCOVERY VERWALTUNGS-GMBH; STEENECK, Christoph; KINZEL, Olaf; ANDERHUB, Simon; HORNBERGER, Martin; KLEYMANN, Gerald; HOFFMANN, Thomas; (191 pag.)WO2018/83241; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics