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. 3144-09-0, name is Methylsulfonamide, A new synthetic method of this compound is introduced below., Product Details of 3144-09-0

General procedure: According to the Scheme 1, 4 mmol of N-(4-Sulfamoylphenyl) acetamide was treated with acetic anhydride (4 mmol) in glacial acetic acid (10 mL). The mixture was stirred at 50C for the predetermined time. The progress of the reaction was monitored by TLC analysis. After the completion of the reaction, the precipitate was collected by filtration and washed with water. The impure precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration to afford N-(4-acetamidophenylsulfonyl)acetamide a1 as the white solid (0.97 g, 95%). The catalytic activities of different heterogeneous catalysts were determined by reactions performed in THF using a 1:1 molar ratio of sulfonamide to acetic anhydride or benzoyl chloride. In a typical route, N-(4-sulfamoylphenyl) acetamide (4 mmol) was treated with acetic anhydride (4 mmol) in the presence of catalyst (0.1 g) in THF (10 mL). After the appropriate time, the catalyst was separated with an external magnetic field, the solvent was evaporated by rotary evaporator. The precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration and was washed with distilled water to afford N-(4-acetamidophenylsulfonyl)acetamide as the white solid (0.95 g, 93%).

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; Ghasemi, Mohammad Hadi; Kowsari, Elaheh; Hosseini, Seyed Kiumars; Tetrahedron Letters; vol. 57; 3; (2016); p. 387 – 391;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 445-28-3, A common heterocyclic compound, 445-28-3, name is 2-Fluorobenzamide, molecular formula is C7H6FNO, 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: The appropriate amide 32a-p, benzhydrazide (40a), or p-toluenesulfonylhydrazide (43a) (1.0 mmol, 1.0 equiv) was placed in a SchlenkKjeldahl reaction flask and the flask was evacuated/argon re-filledthree times. Subsequently, anhyd CH2Cl2 (25 mL) was added and themixture was stirred at r.t. for 10 min before dropwise addition of oxalylchloride (3.0 mmol, 3.0 equiv) followed. The reaction mixturewas then stirred at reflux for 2.5-3.0 h before cooling to r.t. and thesolvent was evaporated in vacuo. Subsequently, the appropriate nucleophile32, 34, 36, 38, 40, 42, 43, or 45 (1.1-1.25 mmol, 1.1-1.25equiv) was rapidly added and the flask was evacuated/argon re-filledbefore anhyd toluene (12 mL) was added. The reaction mixture wasthen stirred at reflux for 2.5-3 h before cooling to r.t. and concentrationto about 1/3 of the initial volume on rotavapor. Hexane was addedto the residue and the obtained precipitate (often sonicated) wascollected by filtration under reduced pressure to yield the crudeproduct. When necessary, the isolated material was purified either bycrystallization from MeOH or flash chromatography on silica gel withhexane-EtOAc as the eluent.

The synthetic route of 445-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hernandez, Anolan Garcia; Grooms, Gregory M.; El-Alfy, Abir T.; Stec, Jozef; Synthesis; vol. 49; 10; (2017); p. 2163 – 2176;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 83948-54-3, name is tert-Butyl (5-bromopentyl)carbamate, 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: C10H20BrNO2

A solution of 4,5-dichlorobenzene-l,2-diamine (350 mg, 1.99 mmol), tert-butyl N-(5-bromopentyl)carbamate (1.05 g, 3.94 mmol), potassium carbonate (819 mg, 5.93 mmol), and sodium iodide (297 mg, 1.99 mmol) in DMF (20 mL) stirred for 18 h at 80 C. The resulting solution was cooled to room temperature, diluted with 50 mL of water, and extracted with 3×40 mL of ethyl acetate. The combined organic phases were washed with 2×30 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography with silica gel (eluting with dichloromethane/methanol (20: 1)) to give tert-butyl 5-(2-amino-4,5-dichlorophenylamino)pentylcarbamate (339 mg, 44%) as brown oil. MS: (ESI, m/z): 362[M+H]+.

The synthetic route of tert-Butyl (5-bromopentyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; LEE, Jennifer; BURNETTE, Pearlie; CHELLAPPAN, Srikumar; BARCZAK, Nicholas; CONTI, Chiara; ESCOBEDO, Jaime A.; HAN, Bingsong; LANCIA, David R., Jr.; LIU, Cuixian; MARTIN, Matthew W.; NG, Pui Yee; RUDNITSKAYA, Aleksandra; THOMASON, Jennifer R.; ZHENG, Xiaozhang; (322 pag.)WO2018/75959; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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: C6H12BF3KNO2

[01299] A mixture of 4-chloro-5 -(trifluoromethyl) -2-[2-(trifluoromethyl)pyrimidin-5 -yl]pyrimidine (300 mg, 0.91 mmol, 1.00 equiv), Pd(PPh3)2C12 (128 mg, 0.18 mmol, 0.20 equiv), sodium carbonate (193 mg, 1.82 mmol, 1.99 equiv), and potassium tert-butyl N-[(trifluoro-lambda4- boranyl)methyl]carbamate (216 mg, 0.91 mmol, 0.99 equiv) in t-butanol (10 mL)/water (1 mL) was stirred for 2 hours at 80C under nitrogen. The resulting solution was diluted with brine, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (1/8) to afford the title compound (230 mg, 60%) as white solid. LCMS [M+H] 424.

The synthetic route of 1314538-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 38267-76-4, 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. 38267-76-4, name is tert-Butyl ethylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00698] Step C: 6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1-((1r,4r)-4-phenoxycyclohexyl)-1H-pyrazolo[4,3-c]pyridine (25 mg, 0.061 mmol), 2-(Dicyclohexylphosphino)-2?,4?,6?-tri-i-propyl-1,1?-biphenyl (29 mg, 0.061 mmol), Cs2CO3 (80 mg, 0.25 mmol) and Pd2(dba)3 (28 mg, 0.031 mmol) were diluted with dioxane (500 muL), followed by the addition of tert-butyl ethylcarbamate (89 mg, 0.61 mmol). The reaction mixture was purged with argon, sealed and heated to 95 C. After 12 h, the reaction was partitioned between ethyl acetate and water, dried over MgSO4, filtered and concentrated. The residue was purified over silica gel (10-60% ethyl acetate/hexanes) to afford tert-butyl ethyl(3-(1-methyl-1H-pyrazol-4-yl)-1-((1r,4r)-4-phenoxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (20 mg, 0.039 mmol, 63 % yield).

The synthetic route of tert-Butyl ethylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, 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: C9H7BrF3NO

Example 6: 2-[3-(4-Bromophenyl)-2-oxo-7-oxa-1 ,4-diazaspiro[4.4]non-3-en-1 -yl]-N-[3- (trifluoromethyl)phenyl]acetamide; 3-(4-Bromophenyl)-7-oxa-1 ,4-diazaspiro[4.4]non-3-en-2-one (D21 ) (0.6g) in DMF (4ml) was cooled to ice bath temp and treated with sodium hydride (81 mg) under argon. The mixture was stirred for 30 minutes when 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D16) (631 mg) in DMF (3ml) was added over 2 hours by syringe pump. The mixture was then allowed to warm to room temp overnight. The solvent was partially removed then in vacuo and then poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried with brine and sodium sulphate and the solvent was removed. The mixture was purified by MDAP and then crystallised by stirring with ether to give the title compound. (414mg) 1H NMR (CDCI3) delta: 2.4-2.6 (2H, m), 3.96 (1 H, m), 4.06 (1 H, m), 4.22 (1 H, m), 4.35 (3H, m), 7.4 (2H, m), 7.65 (3H, m), 7.88 (1 H, m), 8.33 (2H, m) 8.75 (1 H, br) 19F NMR (DMSO) delta: -62.8 (s), Mass Spectrum (Electrospray LC/MS): Found 496/8 (MH+). Ret. time 3.08 min.

The synthetic route of 25625-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; UNIVERSITY OF NOTTINGHAM; WO2008/92877; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 98-18-0, 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. 98-18-0, name is 3-Aminobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Pyridine (1.0 mL, 12.98 mmol) was added dropwise to a mixture of 2- fluoro-4-methyl-benzoyl chloride (2.24 g, 12.98 mmol), 3-aminobenzenesulfonamide (2.235 g, 12.98 mmol) and dichloromethane (40.32 mL) at room temperature. The mixture was allowed to stir at room temperature for 2.5 hours before water (150 mL) was added. The mixture was filtered and the solid was collected by vacuum filtration. The solid was slurried with diethyl ether (30 mL) and filtered (twice). The solid was placed in a vacuum oven at 40 ¡ãC overnight to give 2-fluoro-4-methyl-N-(3-sulfamoylphenyl)benzamide (1.81 g, 45percent) as an off-white solid. ESI-MS m/z calc. 308.06, found 309.5 (M+1) +; Retention time: 1.42 minutes ( 3 minutes run ). 1H NMR (400 MHz, DMSO-d6) delta 10.61 (s, 1H), 8.32 (s, 1H), 7.89 – 7.80 (m, 1H), 7.62 – 7.51 (m, 3H), 7.39 (s, 2H), 7.24 – 7.11 (m, 2H), 2.39 (s, 3H) ppm.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); 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 885-70-1 as follows. Recommanded Product: 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one

(a) 5,11-Dihydro-11-(prop-2-ynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one To a suspension of 7.4 g (0.035 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 150 ml of anhydrous tetrahydrofuran, 44.8 ml (approx. 0.07 mol) of a 15% solution of n-butyl-lithium in n-hexane was added dropwise with stirring at a reaction temperature of from 0 to +10 C. After it had all been added, the mixture was stirred for 30 minutes at ambient temperature before a solution of 4.16 g (0.035 mol) of 3-bromo-prop-1-yne in 25 ml of anhydrous tetrahydrofuran was added dropwise. The resulting mixture was stirred for a further 2 hours at ambient temperature, added to 1 liter of saturated aqueous saline solution and the resulting mixture was extracted exhaustively with ethylacetate. The combined ethylacetate extracts were washed twice more with 100 ml of saturated saline solution, dried over sodium sulphate with the addition of 1 g of activated charcoal and evaporated down in vacuo. The residue was purified on silica gel by chromatography using dichloromethane/ethyl acetate 95/5 (v/v) as eluant. 8.5 g (97% of theory) of colourless crystals were obtained, m.p. 199 C. (decomposition).

According to the analysis of related databases, 885-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Karl Thomae GmbH; US5006522; (1991); A;,
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 4815-28-5 as follows. Product Details of 4815-28-5

General procedure: 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide(4a;1.5 mmol) was suspended in 10 ml butanol and benzaldehydes(5a-5m;1.0 mmol). Conc HCl (0.1 ml) was added to this reaction mixture and heated at 80 C for 12 h or until TLC confirms the completion of reaction. The solid obtained was filtered, washedwith water and dried.

According to the analysis of related databases, 4815-28-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Amawi, Haneen; Karthikeyan, Chandrabose; Pathak, Rekha; Hussein, Noor; Christman, Ryann; Robey, Robert; Ashby, Charles R.; Trivedi, Piyush; Malhotra, Ashim; Tiwari, Amit K.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 1053 – 1065;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 1939-27-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1939-27-1 name is N-(3-(Trifluoromethyl)phenyl)isobutyramide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 3, put a 100ml three-necked bottle with mechanical stirring and thermometer into the ice machine, add 23ml of concentrated sulfuric acid, stir,Addition of 10.75g of iso – butyramide benzotrifluoride until the solid dissolves, keeping the temperature at -5 C, adding 2.3ml of 95% fuming HN03, stirring 3h; Step 4, the above reaction was poured into a certain amount of ice water mixture, was sticky solid, add 80g toluene, stirring,Separation, the upper organic phase was washed three times with 3% sodium bicarbonate solution, followed by three washes, and the solvent was removed by rotary evaporation to give a yellow solid; Step 5, the above yellow solid was added to the flask, 20 ml of ethanol was added, and the mixture was heated to reflux, solid 1% of activated carbon was added, stirred for 5 minutes, and hot filtered.The filtrate was cooled to room temperature, and petroleum ether was slowly added thereto until the solution became turbid. The solution was refrigerated at 0C for 3 hours, filtered, and dried at 60C to obtain flunitamide as a pale yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(3-(Trifluoromethyl)phenyl)isobutyramide, and friends who are interested can also refer to it.

Reference:
Patent; Xuzhou Nuokefei Pharmaceutical Technology Co., Ltd.; Zhao Qingling; Li Weixin; (7 pag.)CN108003051; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics