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. 70-55-3, name is 4-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Methylbenzenesulfonamide

Example 3 p-Aminosulfonyl-benzoic Acid To the solution of 17.1 g (0.1 mol) of p-toluenesulfonamide prepared in Example 1, 20 g (0.5 mol) of sodium hydroxide in 300 ml of water was added in portions 20 g (0.13 mol) of potassium permanganate. The temperature raised to 70 C. spontaneously, keep the reaction mixture in 90 C. for 2 h. The mixture was then cooled and filtered, and the filtrate was acidified with HCl. The resulting precipitate was filtered, and washed with water, dried in vacuo to give the title compound (18.1 g) as white powder, yield 90%, m.p. 291-292 C.

The synthetic route of 70-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guo, Zongru; Cheng, Guifang; Chu, Fengming; US2004/58977; (2004); A1;,
Amide – Wikipedia,
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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. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromomethylbenzenesulfonamide

Example 7 4-(trityithiomethyi)benzenesulfonamide To a stirred solution of triphenylmethanethiol (0.276g, 2equiv) in N,N- dimethylformamide (3 mL) at 0¡ãC was added sodium hydride (60percent w/w dispersion in mineral oil, 0.04g, 2 equiv). When the effervescence had ceased, 4- (bromomethyi)benzenesuifonamide (0.125g, 1 equiv) was added in a single portion and the reaction was allowed to warm to room temperature. HPLC-MS at 20 minutes indicated that conversion was complete. The reaction was quenched with acetic acid (-0.2 mL), concentrated to dryness in vacuo and the subsequent residue partitioned between ethyl acetate and brine. The organic layer was separated, dried over MgS04, filtered, concentrated and purified by flash chromatography (0-50percent ethyl acetate in hexanes). Fractions containing the desired material were concentrated to dryness to furnish the desired compound as a colourless solid (0.200g). f H NMR (400MHz, DMSO-d6) delta (ppm) H), 7.36-7.44 (m, 12H), 7.67-7.73 (m, 2H)

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; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; WINTERS, Geoffrey C.; MANDEL, Alexander Laurence; RICH, James R.; HEDBERG, Bradley John; HSIEH, Tom Han Hsiao; BOURQUE, Elyse Marie Josee; BABCOOK, John; WO2014/144871; (2014); A1;,
Amide – Wikipedia,
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Some common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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. Safety of tert-Butyl (2-hydroxyethyl)(methyl)carbamate

Route ASynthesis of compound 1: 7.5 ml (85 mmol) oxalyl chloride was dissolved in 200 ml DCM and cooled to T < -60 C and 12.1 ml (171 mmol) DMSO in 10 ml DCM was added dropwise (T < -60 C) and stirred an additional 10 min. 10.0 g (57 mmol) N-Boc-N-methylaminoethanol in 40 ml DCM were added dropwise (T < -60 C) and stirred an additional 10 min. 40 ml (285 mmol) Et3N was added dropwise followed by 50 ml DCM (T < -60 C) and stirred for 30 min. The reaction mixture was warmed to 0 C and washed with 3x100 ml water, 100 ml 0.5 M KHS04, 75 ml brine, dried with MgS04 and concentrated in vacuo. The product was purified by column chromatography (Si02, DCM/ethyl acetate, 1 :0 to 9: 1) to give 7.36 g (74%) of compound 1. 1H-NMR (300MHz, CDC13): delta = 1.42/1.46 (s, 9H, Boc), 2.93/2.96 (s, 3H, Me), 3.90/4.01 (s, 2H, CH2), 9.60 (s, 1H, CHO). Z/E isomers. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57561-39-4, its application will become more common. Reference:
Patent; SYNTARGA B.V.; BEUSKER, Patrick, Henry; COUMANS, Rudy, Gerardus, Elisabeth; ELGERSMA, Ronald, Christiaan; MENGE, Wiro, Michael, Petrus, Bernardus; JOOSTEN, Johannes, Albertus, Frederikus; SPIJKER, Henri, Johannes; DE GROOT, Franciscus, Marinus, Hendrikus; WO2011/133039; (2011); A2;,
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Application of 402-46-0, A common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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.

Example 13; 4-Fluoro-{N-4-[N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino]- benzoyl} benzenesulfonamide; A mixture of 4- [N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino] benzoic acid (50 mg, 0.14 mmol), 4-fluorobenzenesulfonamide (49 mg, 0. 28 mmol), 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (54 mg, 0.28 mmol), and dimethylaminopyridine (35 mg, 0.28 mmol) was taken up in dichloromethane (1 mL) and stirred for 18h. The mixture was partitioned between EtOAc (50 mL) and 20% aqueous NH40Ac. The EtOAc was separated, washed with brine, dried (MgS04) and concentrated. The residue was purified by column chromatography (silica gel) eluting with 100% EtOAc to give 38 mg of 4-fluoro-f N 4- [N (3-fluoro-4- methoxyphenyl)-pyridin-3-ylmethylamino]-benzoyl} benzenesulfonamide as a white solid. IH NMR (300 MHz, CDC13) 6 8.5-8. 4 (m, 2H), 8. 11 (m, 2H), 7.7-7. 5 (m, 3H), 7.25 (m, 1H), 7.16 (m, 2H), 7.0-6. 8 (m, 3H), 6.63 (d, J=9.0, 2H), 4.92 (s, 2H), 3.89 (s, 3H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/61458; (2005); A2;,
Amide – Wikipedia,
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Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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: 3984-14-3

A mixture of compound 24-3 (0.465 g, 0.98 mmol) and CDI (0.245 g, 1.57 mmol) in THF (2 mL) was heated at 50 C. for 0.5 h, cooled down and added N,N dimethylsulfamide (0.194 g, 157 mmol) and DBU (0.264 mL, 1.77 mmol). The mixture was stirred for over night. Another portion of DBU (0.13 mL, 0.9 mmol) and the mixture was stirred for another 3 days. The mixture was diluted with EtOAc, washed with cold 1N HCl, brine, dried removed the solvent and purified by flash to afford the Compound 24-4 (0.52 g, 91%). LC-MS retention time: 3.470; MS m/z 579 (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 3984-14-3, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/226593; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1943-79-9, name is Phenyl methylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Phenyl methylcarbamate

Methane sulfonic acid (1.4 g) was added to a mixture of S-{(3R)-5-oxo-1-[(6-phenoxypyridin-3-yl)methyl]pyrrolidin-3-yl)ethanethioate (1.0 g) obtained in Example 38 and isopropyl alcohol (5 mL), and the mixture was stirred at 90C for 5 hours. The reaction mixture was cooled to 60C, potassium carbonate (2.0 g) and isopropyl alcohol (5 mL) were added thereto, and the mixture was stirred at the same temperature for 1 hour. Tri-n-butylphosphine (59 mg) and phenyl methylcarbamate (0.7 g) were added to the mixture, and stirring was continued at the same temperature for another 1 hour. The mixture was cooled to 0 to 10C, citric acid mono hydrate (1.5 g) was added thereto, and then water was added to the mixture while maintaining the same temperature. The mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel chromatography (ethyl acetate) to yield 0.7 g (69%) of the title compound. 1H-NMR (CDCl3) delta: 2.40-2.48(1 H, m), 2.82-2.94(3 H, m), 3.23-3.29 (1 H, m), 3.75-3.81(1 H, m), 4.04-4.08(1 H, m), 4.40-4.49(2 H, m), 5.60 (1 H, brs), 6.87 (1 H, d, J=8.4 Hz), 7, 11-7.22(3 H, m), 7.37-7.42(2 H, m), 7.58-7.62(1 H, m), 8.05(1 H, d, J=2.2 Hz).

The synthetic route of 1943-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1500658; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)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 127828-22-2, Application In Synthesis of tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (300 mg, 1.47 mmol) was taken up in CH2Cl2 (15 mL) along with 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (fenofibric acid, 467 mg, 1.47 mmol) and EDCI (310 mg, 1.47 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford tert-butyl 2-(2-(2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanamido)ethoxy)ethylcarbamate (260 mg, 35%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82210; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 193751-54-1, 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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

6.63 g of mCPBA (70%) was added at 0C to a solution of 4.7 g of N-Boc-cyclopent-3-enyl amine in 80 mL of DCM. The solution obtained was stirred at rt for 1.5 h, charged with 20 mL of 20% sodium thiosulfate, stirred for 10 min, DCM was added, phases obtained were separated and the organic layer obtained was washed with saturated NaHC03 solution. The aqueous layer obtained was extracted twice with DCM, the combined organic layers obtained were dried over magnesium sulfate and solvent was evaporated. 5.2 g of the crude product was obtained which was recrystallized twice from heptane. 917 mg of syn epoxide was obtained in the form of white needles. The mother liquors obtained were subjected to chromatography (silica, toluene/EtOAc = 9: 1 – 7: 1). 3.51 g of anti epoxide in the form of a white amorphous solid was obtained.Syn epoxide: NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.36 (s, 9H), 6.79 (d, 1H, J=8Hz), 1.47 (dd, 1H, J=8Hz and 14Hz), 2.17 (dd, 1H, J=8Hz and 14Hz), 3.44 (s, 2H), 3.54 (m, 1H). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3:1, Rf = 0.4.Anti epoxide: 1H NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.35 (s, 9H), 1.78 (d, 2H, J=15Hz), 1.98 (dd, 1H, J=8Hz and 15Hz), 3.51 (s, 2H), 3.89 (q, 1H, J=8 and 16Hz), 5.70 (d, 1H, J=8Hz). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3: 1, Rf = 0.45.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl cyclopent-3-en-1-ylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NABRIVA THERAPEUTICS AG; RIEDL, Rosemarie; THIRRING, Klaus; HEILMAYER, Werner; WO2012/31307; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 749927-69-3, These common heterocyclic compound, 749927-69-3, name is 4-Bromo-2-fluoro-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.

To a stirred suspension of zinc powder (2.5 g, 38.5 mmol) in anhydrous N,N-d m ethyl form a ide (10 mL) under nitrogen was added iodine (200 mg). After 5 min, a solution of methyl (f?)-2-((/er/-butoxycarbonyl)amino)-3-iodopropanoate (5.0 g, 15.2 mmol) in A( A’-di m ethyl form a i de (10 mL) was added slowly over lOmin. The mixture was stirred at rt for 30min. A suspension of 4-bromo-2-fluoro-Af- methylbenzamide (2.8 g, 12 mmol), Pd2(dba)3 (280 mg, 0.3 mmol), and 2- dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos, 250 mg, 0.6 mmol) in /V,/V- dimethylformamide (10 mL) was added into the zinc reagent mixture. The reaction mixture was heated at 50C and stirred overnight. After cooling, the reaction mixture was quenched with water, diluted with EtOAc and filtered through Celite. The filter cake was washed with EtOAc and the filtrate was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography over silica gel (0-80% EtO Ac/hexane) to afford the desired product as a beige solid (4.0 g, 94%). LC-MS: 377.1 [M+Na]+; 1H NMR (400MHz, CDCl3) d 8.04 (t, 1H, J = 8.1 Hz), 7.02 (d, 1H, J = 8.0 Hz), 6.91 (d, 1H, J = 12.8 Hz), 6.70 (m, 1H), 5.02 (d, 1H, J = 8.0 Hz), 4.60 (m, 1H), 3.73 (s, 3H), 3.18 (dd, 1H, J = 13.8, 5.4 Hz), 3.07 (m, 1H), 3.03 (d, 3H, J = 4.6 Hz), 1.43 (s, 9H).

The synthetic route of 749927-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIODYNE, INC.; MEDINA, Julio Cesar; MCGEE, Larry; WEI, Zhi-Liang; SADLOWSKI, Corinne; SEIDL, Frederick; BHATT, Ulhas; WANG, Xiaodong; NGUYEN, Thomas; SPERANDIO, David; DING, Pingyu; NERURKAR, Alok; LI, Yihong; DUQUETTE, Jason; (307 pag.)WO2019/195634; (2019); A1;,
Amide – Wikipedia,
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These common heterocyclic compound, 6228-73-5, name is Cyclopropanecarboxamide, 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: C4H7NO

To a suspension of 17 (2.00 g, 23.5 mmol) in n-BuOAc (20 mL) at 40-50 C was added 2-bromoacetyl bromide 18b (5.23 g, 25.9 mmol) dropwise, and the mixture was heated to 80 C and stirred for 5 min. After cooling to room temperature, the mixture was stirred for 0.5 h, and then filtered. Wet solids were washed with n-BuOAc (5 mL) and dried in vacuo at 60 C to give the title compound 14b (1.73 g, 36%) as a white solid; mp 153-154 C; 1H NMR (500 MHz, DMSO-d6) delta 0.84-0.88 (m, 2H), 0.89-0.93 (m, 2H), 2.02-2.07 (m, 1H), 4.33 (s, 2H), 11.27 (s, 1H); 13C NMR (125 MHz, DMSO-d6) delta 9.2 (2C), 14.2, 31.7, 167.0, 173.9; IR (ATR) 3255, 3174, 3018, 2947, 1741, 1697, 1513, 1450, 1392, 1283, 1175, 1144, 1103, 1059, 1025, 972, 937, 886, 848, 824, 797, 701, 581, 551, 419 cm-1; Anal. Calcd for C6H8NO2Br; C, 34.98; H, 3.91; N, 6.80; Br, 38.78. Found: C, 34.83; H, 3.78; N, 6.80; Br, 38.95.

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

Reference:
Article; Ishimoto, Kazuhisa; Sawai, Yasuhiro; Fukuda, Naohiro; Nagata, Toshiaki; Ikemoto, Tomomi; Tetrahedron; vol. 69; 40; (2013); p. 8564 – 8571;,
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