Category: amides-buliding-blocks

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. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, A new synthetic method of this compound is introduced below., Safety of 2-Chloro-N-(3-methoxyphenyl)acetamide

General procedure: Various substituted anilines were dissolved in glacial acetic acid at0 C, to this was added over 30 min choloroacetyl chloride (2 equivalents).The reaction mixture was brought to room temperature andstirred overnight. Saturated sodium bicarbonate solution was added tillcomplete neutralization. The resulting precipitate was filtered off andwashed with n-hexane and dried. The resultant product (1) was usedfurther without any purification. Either of 4-hydroxy benzaldehyde(2a), vanillin (2b) or isovanillin (2c) (1 equivalent) was dissolved inacetone and potassium carbonate (2 equivalents) was added. Thencorresponding substituted acetamide (1) was mixed to the stirring solution.Finally, potassium iodide (1.5 equivalent) was added. The reactionmixture was refluxed for 8-10 h. After completion of reaction,the resultant mixture was concentrated and treated with water andextracted with ethyl acetate (3¡Á20 mL). The organic layers werecombined and treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel (60-120)using petroleum ether: ethyl acetate (9:1).

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; Sonawane, Vinay R.; Siddique, Mohd Usman Mohd; Gatchie, Linda; Williams, Ibidapo S.; Bharate, Sandip B.; Jayaprakash, Venkatesan; Sinha, Barij N.; Chaudhuri, Bhabatosh; European Journal of Pharmaceutical Sciences; vol. 131; (2019); p. 177 – 194;,
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191170-76-0, name is Benzyl 4-bromophenethylcarbamate, 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. COA of Formula: C16H16BrNO2

To a solution of benzyl 4-bromophenethylcarbamate (13.7 g, 41.1 mmol) in DMF (40 mL) was added Zn(CN)2 (4.93 g, 41.2 mmol) and Pd(PPh3)4 (4.75 g, 4.11 mmol). The reaction mixture was stirred at 100 C under Ni overnight. TLC showed the reaction completed. The reaction mixture was quenched with water and filtered. The residue was stirred in a mixed solvent of ethyl acetate and hexane (100 mL, EtOAc:Hexane = 1 :6) for 30 min. It was next filtered and dried to afford the title compound as white solid (8.9 g, 77.6%). NMR (500 MHz, DMSO- d6): 7.74 (d, 2H), 7.28-7.41 (m, 8H), 4.99 (s, 2H), 3.25-3.29 (m, 2H), 2.81 (t, 2H).

The synthetic route of 191170-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; YE, Jinqi; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; (0 pag.)WO2020/2968; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, 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 579474-47-8, Recommanded Product: 579474-47-8

Example M4 {4-Fluoro-2-[3-oxo-3-(3-pyridin-3-yl-phenyl)-propionylamino]-phenyl}-carbamic acid tert-butyl ester The title compound was prepared from (2-amino-4-fluoro-phenyl)-carbamic acid tert-butyl ester (Example J2) (83 mg, 0.37 mmol) and 3-oxo-3-(3-pyridin-3-yl-phenyl)-propionic acid tert-butyl ester (Example K1) (109 mg, 0.37 mmol) according to the general procedure M. Obtained as a light yellow amorphous substance (127 mg). MS (ISP) 450 [(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 2-amino-4-fluorophenylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Adam, Geo; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2003/166639; (2003); A1;,
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. 22808-73-7, name is Methyl 4-sulfamoylbenzoate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H9NO4S

B. 4-(4-Oxo-2-m-tolyl-pentanoylsulfamoyl)-benzoic acid methyl ester. To a stirred solution of 4-sulfamoyl-benzoic acid methyl ester (6.01 g, 27.8 mmol), 4-oxo-2-m-tolyl-pentanoic acid (6.35 g, 30.7 mmol), N,N-diisopropylethylamine (12.2 mL, 69.5 mmol), and DMAP (5 mole %) in CH2Cl2 (275 mL) at rt under N2 was added bromo-tripyrrolidino-phosphonium hexafluorophosphate (PyBroP) (18.1 g, 38.9 mmol), and the reaction mixture was allowed to stir overnight. The mixture was diluted with 1 M HCl (100 mL) and CH2Cl2 (150 mL), and the layers were separated. The organic phase was washed with 1 M HCl (1*100 mL), 1N NaOH (1*100 mL) and brine (1*100 mL). The organic layer was dried over Na2SO4, and then filtered, and the solvent was removed under reduced pressure. Purification on silica gel (0-15% EtOAc in hexane) gave. 12.0 g (99%) of desired ester as a white solid. 1H NMR (400 MHz, CDCl3): 8.15 (d, J=8.6 Hz, 2H), 7.99 (d, J=8.6 Hz, 2H), 7.18 (t, J=7.6 Hz, 1H), 7.10 (d, J=7.6 Hz, 1H), 6.87 (m, 2H), 3.97 (s, 3H), 3.93 (dd. J=4.3 and 9.5 Hz, 1H), 3.29 (dd. J=9.5 and 18.1 Hz, 1H), 2.60 (dd. J=4.3 and 18.1 Hz, 1H), 2.28 (s, 3H), 2.07 (s, 3H).

The synthetic route of 22808-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deng, Xiaohu; Mani, Neelakandha; Mapes, Christopher M.; US2006/4195; (2006); 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 53844-02-3

The compound of Reference Example 55 (12.3 g) was dissolved in dimethylformamide (100 ml), and thereto were added cesium carbonate (15.3 g) and the compound of Reference Example 42 (8.75 g), and the mixture was vigorously stirred at 80C for 5 hours. The mixture was filtered to remove the cesium carbonate, and water was added to the filtrate, and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column (ethyl acetate/hexane=1:2) to give the title compound (10.7 g). MS (ESI+) 649 (M++1, 40%).

The synthetic route of 53844-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP2447264; (2012); A1;,
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Some common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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. Recommanded Product: 67442-07-3

Example 10l-(4-teri-butoxy-2-isopropoxy-l,3-benzothiazol-7- l)-2-chloro-ethanoneA solution of n-butyllithium in hexanes (1.6 M, 0.41 mL, 0.65 mmoles) was added dropwise to a pre-cooled (-50 ¡ãC) solution of 7-bromo-4-tert-butoxy-2-isopropoxy-l,3-benzothiazole XVII (225 mg, 0.59 mmoles) in methyl tert-butyl ether (2.5 mL) maintaining a temperature below -45 ¡ãC. The mixture was allowed to warm to -20 ¡ãC and left to stir for 30 minutes. A solution of 2-chloro-N-methoxy-N-methyl acetamide (122 mg, 0.89 mmoles) in methyl tert- butyl ether (2.5 mL) was then added dropwise maintaining a temperature below -15 ¡ãC and the mixture allowed to stir for 20 minutes. The reaction was then quenched by the addition of saturated ammonium chloride solution (2.0 mL) and water (10.0 mL). The aqueous phase was extracted with methyl fert-butyl ether (2 x 10 mL) and the combined organic phases were dried (MgSC^), filtered and evaporated to give a pale orange solid. Purification by flash chromatography (isohexane/EtOAc, 95/5 to 90/10) gave title compound XVI as a beige solid (120 mg, 0.35 mmoles).1H NMR (500 MHz, CDC13) delta 7.75 (d, J= 8.5 Hz, 1H), 7.11 (d, J= 8.5 Hz, 1H), 5.46 (hept, J= 6.2 Hz, 1H), 4.79 (s, 2H), 1.50 (s, 9H), 1.47 (d, J= 6.2 Hz, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67442-07-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARNWELL, Neil; CORNWALL, Philip; GILL, Duncan, Michael; HOWELL, Gareth, P.; MEADOWS, Rebecca, Elizabeth; MERIFIELD, Eric; MITCHELL, Christopher, William; MURUGAN, Andiappan; O’KEEFE, Philip; PATEL, Zakariya, Mohamed; ROSE, James, Barry; SINGLETON, John; WITHNALL, Jane; WO2012/156693; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 115643-59-9, name is 2-Amino-6-fluorobenzamide, 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 115643-59-9, Safety of 2-Amino-6-fluorobenzamide

An aromatic amine 1t-1 (0.20 mmol), a platensimycin acid (0.10 mmol), and2-(7-Azobenzotriazole)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) (0.30 mmol) was added to the reaction flask and 1.0 ml was added.N,N-dimethylformamide, stirring at room temperature; slowly adding triethylamine (0.45 mmol), stirring for 12 hours, rotary evaporationSolvent to obtain a crude product, which is subjected to column chromatography to obtain a platensimycin analog2t-1, yield 42%.

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; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Ha Yao Cihang Pharmaceutical Co., Ltd.; Duan Yanwen; Shen Ben; Huang Yong; Zhu Xiangcheng; Qiu Lin; Tian Kai; (39 pag.)CN107793388; (2018); A;,
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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. 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H21NO3

To a suspension of 60% sodium hydride dispersion (0.270 g, 6.75 mmol) in 20 mL DMSO, (lR,3r,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (1.0 g, 4.399 mmol) was added. After stirring at room temperature for 20 min, l-(benzyloxy)-4-fluorobenzene (0.89 g, 4.401 mmol) was added and mixture was stirred at 90C (oil bath). After 2.5 d, dark mixture was extracted with water and AcOEt (3x). Combined organic phases were dried over MgS04, filtered, and concentrated. Residue (ca. 3 g) was dissolved in 40 mL CH2C12 and triethylamine (1 mL, 7.175 mmol) and di-teri-butyl dicarbonate (0.961 g, 4.401 mmol) were added. After 10 min, mixture was transferred into a separatory funnel and extracted with water and CH2C12. Organic phases was dried over MgSO/t, filtered, and concentrated. Residue was purified by Biotage column chromatography (Si02, hexane/ AcOEt gradient) to give (lR,3r,55)-teri-butyl 3-(4-(benzyloxy)phenoxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (0.34 g, 0.830 mmol, 18.9%) as a white solid. Exact mass calculated for C25H31F6N04: 409.23, found: LCMS m/z = 410.2 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.47 (s, 9H), 1.93-1.97 (m, 4H), 2.07-2.17 (m, 4H), 4.49-4.53 (m, 2H), 4.50-4.52 (m, 1H), 5.01 (s, 2H), 6.75-6.77 (m, 2H), 6.89-6.91 (m, 2H), 7.31-7.43 (m, 5H).

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; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 116332-54-8, name is 4-Fluoro-N-methoxy-N-methylbenzamide, 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. COA of Formula: C9H10FNO2

PREPARATIVE EXAMPLE 2 4-Fluoro-2-(2-pyridyl)acetophenone (2) To a solution of lithium diisopropylamide (Aldrich Chemical Co. 2.0M in heptane,THF ethylbenzene) 5.2 mL (10.5 mmol) in 6 mL of anhydrous THF at -78 C. under nitrogen was added 0.93 g (10 mmol) of 2-picoline dropwise. The reaction mixture was stirred for 20 minutes and then treated with a solution of 1.71 g (5.3 mmol) of 4-fluoro-(N-methyl-N-methoxy)-benzamide in THF. The reaction mixture was warmed to 0 C. and quenched by addition of 10 mL of brine. The mixture was extracted with ethyl acetate (3*10 mL) and the combined organic phases were dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo to give a solid. H1 NMR (CDCl3 300 MHz): 4.49 (s); 6.0 (s); 6.97 (m); 7.-3-7.12 (m); 7.62 (m); 7.82 (m); 8.10 (dd); 8.28 (bd); 8.57 (bd). The compound exists in a keto/enol equilibrium as determined by H1 -NMR. FAB ms:216 (M+ +1).

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

Reference:
Patent; Merck & Co., Inc.; US5837719; (1998); A;,
Amide – Wikipedia,
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Electric Literature of 224789-21-3, 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 224789-21-3 as follows.

Example 8 Preparation of 2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-t hione 2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-one (50g (0.16mol)), phosphorus pentasulfide (17.8g (0.08mol)), pyridine (250ml)were added into a 500ml three-neck flask with a mechanical stirrer, stirred, heated and refluxed for 6 hours, TLC tracing was performed until the reactants were totally disappeared. The solvent pyridine was removed by distilling under reduced pressure, concentrated ammonia water ((25-28%) 75ml)and ethanol (300ml)were added, heated and refluxed for 30 min. It was cooled, filtered, dried, and crude product (45g)was obtained. The crude product was heated and solved into chloroform (150ml), activated carbon (5g)was added, stirring and reflux was performed for 30 min, it was filtered and the filtrate was washed with saturated brine and water consequently and dried with magnesium sulfate anhydrous, chloroform was removed by distilling, the obtained solid was re-crystallized with ethanol and dried, solid (38g)was obtained with a yield of 72%.

According to the analysis of related databases, 224789-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; WANG, Jianping; WANG, Jianguo; EP2666776; (2013); A1;,
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Amide – an overview | ScienceDirect Topics