Category: amides-buliding-blocks

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. 354-38-1, name is 2,2,2-Trifluoroacetamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C2H2F3NO

Intermediate 186 (0.43 g, 1.22 mmol) was dissolved in DCM (20 mL) and 2,2,2- trifluroacetamide (0.28 g, 2.49 mmol), magnesium oxide (0.21 g, 5.1 mmol), rhodium(II) acetate dimer (0.028 g, 0.064 mmol) and iodobenzene I,I-diacetate (0.53 g, 1.65 mmol) were added. After 18 h at r.t. the pink solution was filtered through a pad of celite and concentrated in vacuo. The residue was purified by column chromatography (Si02, 20- 60% EtOAc:DCM) to yield the title compound (0.39 g, 90%). HPLC-MS : MH+ mlz 431 , RT 2.00 minutes

According to the analysis of related databases, 354-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 154748-63-7, name is tert-Butyl (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 154748-63-7, name: tert-Butyl (3-hydroxycyclobutyl)carbamate

c) tert-butyl (3-tosyl-cyclobutyl)-carbamate18.7 g (100 mmol) tert-butyl (3-hydroxy-cyclobutyl)-carbamate and 12.1 g (120 mmol) triethylamine are placed in 500 mL chloroform. 20.5 g (105 mmol) tosyl chloride, which is dissolved in 150 mL chloroform, is added dropwise to this solution at 00C with stirring. Then the reaction mixture is allowed to come up to 200C and stirred for a further 2 h. The organic phase is washed successively with water, with dilute hydrochloric acid, with sodium hydrogen carbonate solution and again with water. The organic phase is dried on magnesium sulphate and the solvent is eliminated in vacuo. Yield: 28.3 g MS (ESI): 342 (M +H)+

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2007/115999; (2007); A1;,
Amide – Wikipedia,
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Application of 57561-39-4, A common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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 mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and ethyl chlorocarbonate (1.25 mL) was dropwise added. The mixture was stirred overnight at room temperature and ethyl acetate (50 mL) was added. The mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 2 hrs., diethyl ether (10 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.66 g) as a white solid.1H-NMR(DMSO-d6) : 1.23(3H,t,J=7.1Hz), 2.54 (3H,s), 3.16-3.22(2H,m), 4.15(2H,q,J=7.1Hz), 4.32-4.37(2H,m), 9.25 (2H,br).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1607088; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, 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: 4-Bromomethylbenzenesulfonamide

[0498] Ethyl 3-oxo-3-phenylpropanoate (150 mmol) and cesium carbonate (C52CO3, 226 mmol) were dissolved in DMSO (50 ml). The reaction mixture was stirred at rt for 10 minutes at which time potassium iodide were added (KI, 150 mmol) and 4-(bromomethyl)- benzenesulfonamides (165 mmol). The resulting mixture was stirred at rt for 1 h. Upon completion as detected by LCMS, the reaction mixture was diluted with a large excess of ethyl acetate and filtered through celite. The filtrate was washed with 1 M HC1, sat aq NH4C1 and brine, dried over Na2504, filtered, and concetrated under reduced pressure. The residue was purified directly on silica using gradient elution (20-40 percent ethyl acetate in hexanes over 16 CV).

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

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Amide – Wikipedia,
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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. 703-12-8, name is 4-Bromo-N-methylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 703-12-8

4-Bromo-N-methylbenzenesulfonamide (100 mg, 0.40 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (72 mg, 0.48 mmol), potassium fluoride (76 mg, 1.3 mmol), and tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.0 mL) was added. Tri-t-butylphosphine (60 muL, 0.02 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica and rinsed with ethyl acetate. The solvent was concentrated in vacuo to provide the crude product. The crude product was pre-adsorbed onto the Celite reagent and purified via Isco chromatography (the Redisep column, silica, gradient 5-50% ethyl acetate in hexane) to afford 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-methylbenzenesulfonamide (28 mg, 25%). MS (ESI) m/z 275. HPLC purity 100.0% at 210-370 nm, 9.0 min.; the Xterra RP18 column, 3.5mu, 150*4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

The synthetic route of 703-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2008/221201; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 55512-05-5,Some common heterocyclic compound, 55512-05-5, name is 3-(Methylsulfonamido)benzaldehyde, molecular formula is C8H9NO3S, 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.

Under argon and at 0 C., 83 mg (0.417 mmol) of N-(3-formylphenyl)methanesulfonamide (Example 86A) were initially charged in 1 ml of abs. tetrahydrofuran. At 0 C., 99 mg (0.833 mmol) of methylmagesium bromide (3 M in diethyl ether) were added dropwise (resulting in the formulation of a precipitate), and the reaction solution was stirred at this temperature for 2 h. The reaction solution was quenched with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Yield: 80 mg (89% of theory) LC-MS (Method 8): Rt=1.15 min; MS (ESIpos): m/z=214 [M-H]-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Methylsulfonamido)benzaldehyde, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Vakalopoulos, Alexandros; Meibom, Daniel; Nell, Peter; Sussmeier, Frank; Albrecht-Kupper, Barbara; Zimmermann, Katja; Keldenich, Joerg; Schneider, Dirk; Krenz, Ursula; US2013/210795; (2013); A1;,
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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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, A new synthetic method of this compound is introduced below., Product Details of 121492-06-6

Step 1 [0216] A solution of N-Boc-N-methylethylenediamine (1 g, 5.74 mmol) and sulfamide (1.1 g, 11.48 mmol) in dioxane (20 mL) was stirred at reflux under N2 atmosphere (monitored by TLC). The mixture was then filtered to remove the insoluble material and the filtrate was concentrated under reduced pressure and treated with ethyl acetate. The insoluble material was again removed by filtration and the filtrate concentrated under reduced pressure to give the desired product in 96% yield.

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; FOB SYNTHESIS; WO2005/123066; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2227-79-4, name is Benzothioamide, 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. Application In Synthesis of Benzothioamide

A mixture of benzenecarbothioamide (6.86 g) , 1,3- dichloroacetone (6.35 g) and toluene (50 mL) was heated under reflux for 3 hr. The reaction mixture was cooled, and water was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (9.77 g) . MS: [M+H]+ 210.1.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAJITA, Yuichi; MIKAMI, Satoshi; MIYANOHANA, Yuhei; KOIKE, Tatsuki; DAINI, Masaki; OYABU, Norio; OGINO, Masaki; TAKEUCHI, Kohei; ITO, Yoshiteru; TOKUNAGA, Norihito; SUGIMOTO, Takahiro; MIYAZAKI,Tohru; ODA, Tsuneo; HOASHI, Yasutaka; HATTORI,Yasushi; IMAMURA, Keisuke; (413 pag.)WO2019/27058; (2019); A1;,
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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

To a stirred solution of 5-methylthiazole 75 (9 g, 90.90 mmol) in anhydrous THF (200 mL) under inert atmosphere was added n-butyl lithium (40 mL, 99.99 mmol) dropwise for 30 min at -78 oC. To this was added N-methoxy-N-methylacetamide (11.24 mL, 109.1 mmol) dropwise for 20 min at -78 oC, followed by warming to 0 oC and stirring for 16 min. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution and extracted using EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 3% EtOAc/ hexanes to afford compound 76 (12 g, 94%) as pale yellow liquid. TLC: 10% EtOAc/ hexanes (Rf: 0.5); 1H NMR (DMSO-d6, 400 MHz): delta 7.83 (s, 1H), 2.58 (s, 3H), 2.54 (s, 3H).

According to the analysis of related databases, 78191-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASSEMBLY BIOSCIENCES, INC.; TURNER, William, W., Jr.; LI, Leping; HAYDAR, Simon, Nicolas; BURES, Mark, G.; RAI, Roopa; FRANCIS, Samson; ARNOLD, Lee, Daniel; (0 pag.)WO2018/160878; (2018); A1;,
Amide – Wikipedia,
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These common heterocyclic compound, 316146-27-7, name is N-(4-Bromophenyl)-3-phenylpropanamide, 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. Formula: C15H14BrNO

General procedures:; Scheme 2; An acid (1 equiv), HATU (1 equiv) and DIEA (3 equiv) were added to a solution of 4-bromo-aniline (1 equiv) in DMF. The mixture was stirred at room temperature until the starting material disappeared (detection by LC-MS). The solution was diluted with EtOAc and washed with saturated aqueous NaHCO3. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude bromide 2-1. The bromide 2-1 (1 equiv) and the boronic acid ester (1.5 equiv) were dissolved in degassed dioxane/H2O (5:1 by volume) in a sealed tube. Pd(PPh3)4 (0.03 equiv) and 2M solution Of K2CO3 (3 equiv) were added sequentially. The mixture was heated at 95 0C for 2h. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate and concentrated in vacuo. The residue was then purified by preparative HPLC to give the product 2-2 as a solid (65percent-80percent yield in two steps).; Example 27. N-(4-(lH-pyrazol-4-yl)phenv0-3-phenylpropanamide; Procedures in Scheme 2 were utilized to synthesize this compound. LC/MS: Ci8HnN3O (M+l) 292. Single peak at both 215 nm and 254 nm in analytical HPLC traces.

The synthetic route of N-(4-Bromophenyl)-3-phenylpropanamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FENG, Yangbo; LOGRASSO, Philip; SCHROETER, Thomas; YIN, Yan; WO2010/36316; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics