Tag: M.W=200-300

Synthetic Route of 830-43-3, A common heterocyclic compound, 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, molecular formula is C7H6F3NO2S, 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 10-mL screw cap glass tube with a PP-cap was charged with a magnetic stirring bar, sulfonamide 1 or 6 (0.25 mmol, 1.0 equiv), glyoxylic acid monohydrate (2; 30.0 mg, 0.33 mmol, 1.3 equiv), phenylboronic acid (3a; 61.0 mg, 0.5 mmol, 2.0 equiv), and nitromethane (1.5 mL, 0.17 M wrt sulfonamide) and firmly closed. The resulting mixture was stirred at 60 C for 12 h. After cooling to r.t., the mixture was diluted with acetone and filtered through a short plug of Celite/silica gel. The plug was rinsed with additional acetone and the filtrate was concentrated under reduced pressure. Purification of the crude residue by flash column chromatography afforded the product.

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; Diehl, Andreas M.; Ouadoudi, Omar; Andreadou, Eleni; Manolikakes, Georg; Synthesis; vol. 50; 19; (2018); p. 3936 – 3946;,
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121496-39-7, name is tert-Butyl benzyl(2-hydroxyethyl)carbamate, 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 tert-Butyl benzyl(2-hydroxyethyl)carbamate

EXAMPLE IV N-tert.-Butoxycarbonyl-N-benzyl-glycine aldehyde STR32 Variant A 14.65 g (58.3 mmol) of the compound from Example III and 37.3 g (175 mmol) of pyridinium chlorochromate (Aldrich) are added to 500 ml of dichloromethane and the mixture is stirred at room temperature for 2 hours. The mixture is concentrated in a rotary evaporator and quickly filtered through a frit using 600 g of silica gel 60 (Merck) and a step gradient of 1 lof dichloromethane, 1l of dichloromethane/methanol 98/2 and 1.5 l of dichloromethane/methanol 95:5. 500 ml fractions were taken, and the product-containing eluates were combined, dried over sodium sulphate and concentrated in a rotary evaporator. Yield: 4 g (27.5% of theory)

The synthetic route of 121496-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US5095006; (1992); A;,
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Synthetic Route of 912444-89-4,Some common heterocyclic compound, 912444-89-4, name is 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate, molecular formula is C14H23NO4, 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 suspension of NaH (21.2 g, 0.318 mol, 60% dispersion in mineral oil) in DMSO (650 mL), S,S,S-trimethylsulfoxonium iodide (72.9 g, 0.331 mol) was added in small portions and stirred at rt for 1 h until gas evolution ceased. A solution of 1-tert-butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate (9) (34.3 g, 0.127 mol) in DMSO (150 mL) was added dropwise and the reaction mixture was stirred at 50 C overnight. The resulting solution was cooled to rt, poured into ice-cold H2O (1 L) and extracted with t-BuOMe (3×700 mL). The combined organic extracts were washed with brine (3×500 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The product was purified by column chromatography (gradient hexane to hexane – t-BuOMe (7:3) as eluent). Yield: 19.8 g (55 %); colourless oil. 1H NMR(500 MHz, CDCl3): delta 4.14 – 4.06 (m, 2H), 3.98 – 3.78 (m, 2H), 3.10 (s, 1H), 2.96 (s, 1H), 2.77 (dd, J=15.3, 6.4 Hz, 1H), 2.36 (dt, J=14.1, 6.5 Hz, 1H), 1.75 – 1.65 (m, 1H), 1.49 (dd, J=9.2, 4.3 Hz, 1H), 1.43 (s, 9H), 1.37 – 1.26 (m, 2H), 1.23 (t, J=7.1 Hz, 3H), 0.77 (t, J=6.6, 4.3 Hz, 1H). 13C NMR(126 MHz, CDCl3): delta 175.4, 155.1, 79.3, 60.6, 47.6, 47.2, 32.7, 32.4, 28.4, 27.7, 26.9, 24.7, 14.2. MS (APCI): m/z = 284 [M+H]+. Anal. Calcd. for C15H25NO4: C 63.58; H 8.89; N 4.94. Found: C 63.86; H 8.58; N 5.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate, its application will become more common.

Reference:
Article; Yarmoliuk, Dmytro V.; Serhiichuk, Dmytro; Smyrnov, Vladyslav; Tymtsunik, Andriy V.; Hryshchuk, Oleksandr V.; Kuchkovska, Yuliya; Grygorenko, Oleksandr O.; Tetrahedron Letters; vol. 59; 52; (2018); p. 4611 – 4615;,
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35623-11-1, name is 3-[(Methylamino)sulphonyl]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. Application In Synthesis of 3-[(Methylamino)sulphonyl]benzoic Acid

A mixture of 3-methylsulfamoyl-benzoic acid (988 mg, 4.59 mmol) and SOCl2 (5 ml) was stirred at 70 C for 10 h. The mixture was concentrated under reduced pressure and azeotroped with toluene to give the crude carboxylic acid chloride. n-BuLi (5.83 ml, 15.2 mmol, 2.6 M in hexane) was added to a solution of 1,1,1,3,3,3- hexamethyldisilazane (3.2 ml, 15.2 mmol) in THF (15 ml) at -78 C. After stirring for 1 h at -78 C, ?- butyrolactone (395 mg, 4.59 mmol) in THF (5 ml) was added. After stirring for 15 min at -78 C, crude acid chloride in THF (15 ml) was added to the reaction mixture. The mixture was allowed to slowly warm to room temperature and stirring was continued for 1 h. The mixture was acidified with 5 M HCl aq. and extracted with diethyl ether twice. The combined organic extract was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (n-hexane/EtOAc) to afford the titled compound (1.43 g, quant.) as colorless oil.

The synthetic route of 35623-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kawada, Hatsuo; Ebiike, Hirosato; Tsukazaki, Masao; Nakamura, Mitsuaki; Morikami, Kenji; Yoshinari, Kiyoshi; Yoshida, Miyuki; Ogawa, Kotaro; Shimma, Nobuo; Tsukuda, Takuo; Ohwada, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 673 – 678;,
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Adding a certain compound to certain chemical reactions, such as: 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, 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 35303-76-5, COA of Formula: C8H12N2O2S

General procedure: To a cooled solution of triphosgene (1.41mmol) in THF at 0°C, a mixture of primary amine (3.52mmol) and N,N-diisopropylethylamine (DIPEA, 7.04mmol) was added. The reaction mixture was stirred at the same temperature for 30min and then the other amine (3.52mmol) was added. The reaction mixture was slowly allowed to attain ambient temperature and further stirred for 8h. After the completion of the reaction, water was added to the reaction mixture and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was subjected to column chromatography to obtain the pure compounds.

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:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Boggu, Pulla Reddy; Sharma, Niti; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Son, Min-Jeong; Woo, Sun-Hee; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1869 – 1887;,
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Synthetic Route of 676371-64-5, 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 676371-64-5 as follows.

[0204] A solution of 16-1 ((prepared according to Eur. J. Org. Chem. 2004, 493- 498), 0.400 g, 1.67 mniol) in THF (6.2 mL) was cooled to 0 C and treated with MgBrCH3(4.0M in Et20, 2.1 mL, 6.22 mmol). After 15 mins, the reaction was warmed to rt. After 4 h, the reaction was cooled to 0 C and quenched with sat. aq. NH4CI solution (5 mL). After warming to rt, the reaction was diluted with EtOAc and H2O. The organic layer was separated. The aqueous layer was saturated with NaCl(s) and then extracted with EtOAc (3 x 20 mL). The combined organics were dried (Na2S04) and concentrated under reduced pressure to afford an oil that was further purified by flash chromatography (S1O2, 0-100% EtOAc/Hexanes) to afford 16-2 (0.190 g, 63%) as a colorless oil. 1H NMR (400 MHz, CDCb) delta 1 .93 (s, 6H), 1 .47 (s, 9H), 1.21 is. 6H).

According to the analysis of related databases, 676371-64-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KALYRA PHARMACEUTICALS, INC.; BUNKER, Kevin, Duane; GUO, Chuangxing; GRIER, Mark, Charles; HOPKINS, Chad, Daniel; PINCHMAN, Joseph, Robert; SLEE, Deborah, Helen; HUANG, Qinhua; KAHRAMAN, Mehmet; (122 pag.)WO2016/44331; (2016); A1;,
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Related Products of 919475-15-3, These common heterocyclic compound, 919475-15-3, name is 2-(4-(Benzyloxy)phenyl)-N,N-dimethylacetamide, 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 certain embodiments, the following procedure was employed. 150 g of 2-(4- benzyloxy)phenyl-N,N-dimethylacetamide, 945 g (1062 mL) of THF was charged to a 5 L jacketed reactor. 550 mL of isopropylmagnesium chloride (2.0 M in tetrahydrofuran) was added and the mixture was stirred for 1 h. 115 g of cyclohexanone was added to the reactor and mixed for 1 h. 360 g of RedAI (sodium bis(2-methoxyethoxy)aluminum hydride-65percent w/w in toluene) was added to the reactor and stirred for 16 h. When the reaction was complete the mixture was- 66 -LAI-2932341vl added to 2005 g of 22percent w/w aqueous citric acid. 420 g (600 mL) of heptane was charged to the reactor and stirred for 15 min. The stirring was stopped and the top layer was removed. 250 g of 50percent NaOH was added to adjust the pH to 9-10, followed by stirring. 1114 g (1500 mL) of MTBE was added to the reactor. The mixture was warmed to 45 +/- 5°C to dissolve the solids. The stirring was stopped and the bottom layer was removed. The organic layer was washed twice with 750 g of water at 450C. 750 mL of MTBE was removed by distillation and 750 mL of methanol was added. About 750 mL of MTBE/methanol was removed by distillation and 300 g of methanol and 300 g of water were added. The slurry was cooled to 0 0C and stirred for 30 min. The slurry was filtered and the solid washed with 375 g of (4:1 methanohwater). The solid was dried to yield 161 g of 1-(2-(dimethylamino)-1-(4-benzyloxyphenyl)ethyl) cyclohexanol.[00261] In certain embodiments, the following procedure was employed. To a 200 gallon reactor was charged 22.98 kg of 2-(4-benzyloxy)phenyl-N,N-acetamide and 145.1 kg of THF. With agitation, the temperature was adjusted to 5 0C to 10 0C. To the reactor was charged 82.9 kg of isopropylmagnesium chloride, 2.0M in THF, while maintaining the temperature between 5 0C to 35 0C. The lines were rinsed with 2.78 kg of THF. The contents were agitated for 61 minutes at 10 0C to 20 0C. To the reactor was added 9.31 kg of cyclohexanone while maintaining the temperature between 5 0C to 35 0C. The lines were rinsed with 2.77 kg of THF. The temperature was adjusted to 15 0C to 25 0C and the contents were agitated for 17 minutes at this temperature range after which the reaction was complete. To the reactor was charged 55.8 kg of sodium bis(2-methoxyethoxy)aluminum hydride (65 wtpercent in toluene) while maintaining the temperature at 15 0C to 35 0C. The contents were agitated for 10 h (<3percent starting material remained). The reaction mixture was added to 334.1 kg of 22percent citric acid solution cooled to 0 0C to 2 °C. THF (22.9 kg) and n-heptane (63.3 kg) were added to the reaction. The mixture was agitated for 15 minutes then the stirring was stopped and the phases were allowed to separate. The top layer was removed and the reactor was charged with 45.4 kg of 50percent sodium hydroxide. The reactor was charged 169.9 kg of MTBE and the temperature was adjusted to 40-50 0C. The contents were agitated for 14 minutes and the agitation was stopped to allow the phases to separate for 15 minutes. The aqueous layer was removed and 115 L of USP purified water was added. The temperature was adjusted to 40 0C to 50 0C. The contents were agitated for 15 minutes and the agitation was stopped to allow the phases to separate for 13 minutes. The aqueous bottom layer was removed. The reactor was charged with 115 L of USP purified water and the temperature was adjusted to 40 0C to 50 0C. The contents were agitated for 15 minutes and the agitation was stopped to allow the phases to separate. The aqueous bottom layer was removed. The solution was distilled under vacuum to a final volume of 188 L. To the reactor- 67 -LAI-2932341vl was charged 115.2 kg of methanol and the solution was distilled under vacuum to a final volume of 131 L. To the reactor was charged 46.0 kg of methanol and 57 L of USP purified water. The temperature was adjusted to 0 0C. The slurry was stirred for 41 minutes at -5 0C to 5 CC and the mixture was filtered. The cake was washed with 46.2 kg of methanol and 11.6 kg of USP purified water (cooled to -5 0C to 5 0C). The wet cake (30.66 kg) was dried at 40-50 0C to yield 24.47 kg of 1-(2-(dimethylamino)-1-(4-benzyloxyphenyl)ethyl)cyclohexanol.

The synthetic route of 919475-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEPRACOR INC.; WO2008/103461; (2008); A2;,
Amide – Wikipedia,
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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 104060-23-3 as follows. HPLC of Formula: C13H19NO3

193-2 2-(4-tert-Butoxycarbonylaminophenyl)ethyl-4-(2-bromo-5-methoxybenzyl)piperidine Methanesulfonyl chloride (120 mul, 1.56 mmol) was added dropwise to a solution of 2-(4-tert-butoxycarbonylaminophenyl)ethanol (354 mg, 1.56 mmol) and triethylamine (430 mul, 3.12 mmol) in dichloromethane (5 ml) under ice-cooling, and the reaction mixture was stirred as it was for 2 hours. The solvent was distilled off and the resulting residue was suspended in acetonitrile (5 ml) together with a free compound obtained by treating the compound of Example 1 (500 mg, 1.56 mmol) by the same method as in Example 11, potassium carbonate (431 mg, 3.12 mmol) and potassium iodide (259 mg, 1.56 mmol). The resulting suspension was stirred at 60 C. for 1 hour, heated under reflux for 4 hours, and then allowed to cool. After filtration, the filtrate was concentrated and the residue was purified by a silica gel column chromatography (chloroform/methanol=50/1 to 20/1) to obtain the title compound (587 mg, 73%) as a colorless oil.

According to the analysis of related databases, 104060-23-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO PHARMACEUTICALS COMPANY LIMITED; US2003/191126; (2003); A1;,
Amide – Wikipedia,
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Synthetic Route of 180079-94-1, 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. 180079-94-1, name is tert-Butyl 3-aminophenethylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step-4: Synthesis of 3-(2-aminoethyl) aniline A solution of tert-butyl (3-aminophenethyl) carbamate (3.0 g, 12.71 mmol, 1 eq) in TFA (10 mL) was stirred at room temperature for 1 h. The reaction liquid was concentrated to obtain, 3-(2-aminoethyl) aniline (2.5 g, crude) as brown liquid.

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

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); 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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Step 14-sulfamoylbenzoyl azide (JS129)4-sulfamoylbenzoic acid (1 .00 g, 4.97 mmol), triphenylphosphine (2.61 g, 9.94 mmol) and sodium azide (0.388 g, 5.96 mmol) were suspended in anhydrous acetone (10 ml). To this milky white suspension was added trichloroacetonitrile (0.997 ml, 9.94 mmol) drop wise and the reaction was left to stir at RT for 18 h. The solvent was removed in vacuo and the resulting dark yellow slurry was diluted with CH2CI2 and washed with H20 and brine, dried (MgS04), filtered and concentrated in vacuo. Flash chromatography (Pet Ether; 3:1 to 2:1 to 1 :1 Pet Ether/EtOAc) afforded the title compound as a white solid (906.9 mg, 4.01 mmol, 80.7%). Mpt: 1 18 C; Rf = 0.23 (1 :1 Pet Ether/EtOAc); IR (vmax/cm”1, thin film): 3362 (aromatic C-H stretch), 3258 (N-H stretch), 2137 (N=N=N stretch), 1687 (CO stretch), 1339 (S=0 stretch, asymmetrical), 1238, 1 155 (S=0 Symmetrical stretch); 1H NMR (600 MHz, CD3OD): deltaEta = 8.02 (ap.d, J = 6.9 Hz, 2H, 4-H), 8.18 (ap.d, J = 6.8 Hz, 2H, 3-H); 13C NMR (150 MHz, CD3OD): 5C = 127.6 (C-4), 131.0 (C-3), 134.9 (C-2), 150.2 (C-5), 172.8 (C-1 ); LRMS/HRMS m/z (ES+): no product mass present; Anal. Calcd. for C7H6N403S: C, 37.17; H, 2.67; N, 24.77. Found C, 37.27; H, 2.49; N, 24.40%.

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; UCL BUSINESS PLC; BIRKBECK COLLEGE; WAKSMAN, Gabriel; TABOR, Alethea; SAYER, James; WALLDEN, Karin; WO2012/168733; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics