Month: September 2021

Application of 26638-53-9, The chemical industry reduces the impact on the environment during synthesis 26638-53-9, name is 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, I believe this compound will play a more active role in future production and life.

6-Methyl-3- (methylthio) dibenzo [c, f] [1,2] thiazepin-11 ( 6H) -one 5,5-dioxide (3i) . To a solution of sodium thiomethoxide (116 mg, 1.65 mmol) in anhydrous DMF (2.0 mL) was added ketone 3d (462 mg, 1.50 mmol) and the resulting yellow suspension was stirred at room temperature for 1 h. Additional sodium thiomethoxide (26.3 mg, 0.375 mmol) was then added and stirring continued for a further 15 min. The reaction was then quenched with water (10 mL) and extracted with CH2CI2 (10 mL, 2 5 mL) . The combined organics were washed with water (20 mL) , dried over Na2SC>4, and concentrated to yield a yellow oil containing residual DMF. This crude was diluted with Et20 and chilled on ice causing the product to crystallize as pale-yellow needles. These crystals were washed with several small portions of ice-cold Et20 and dried to give the pure ketone 3i (331 mg, 69percent) . *H NMR (500 MHz, CDCI3) delta 8.31 (dd, J = 8.1, 1.6 Hz, 1H) , 7.92 (d, J = 8.3 Hz, 1H) , 7.73 (d, J = 2.0 Hz, 1H) , 7.62 (ddd, J = 8.0, 7.4, 1.7 Hz, 1H) , 7.48 (dd, J = 8.3, 2.0 Hz, 1H) , 7.40 – 7.33 (m, 2H) , 3.33 (s, 3H) , 2.59 (s, 3H) ; 13C NMR (126 MHz, CDC13) delta 189.5, 146.5, 141.4, 137.7, 134.7, 132.4, 132.2, 131.8, 131.7, 129.2, 126.4, 125.2, 121.4, 39.3, 15.0. LR-MS calcd. for C15H14NO3S2 [M+H]+ 320.04, found 320.75.

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-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; KRUEGEL, Andrew; SAMES, Dalibor; JAVITCH, Jonathan A.; (187 pag.)WO2018/170275; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

154350-29-5, name is Cyclopropanesulfonamide, 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. Formula: C3H7NO2S

(15, 4R, 65, 145, 18R)-7-c-14-tert-Butoxycarbonylamino-18-(tert- butyldimethylsilyloxy)-2,15-dioxo-3, 12,16-triazatricyclo[ 14.3.0.04’6]nonadec-7-ene- 4-carboxylic acid (490 mg, 0.79 mmol) was dissolved in 15 mL of THF and treated with CDI (179 mg, 1.10 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere.) After refluxing the reaction mixture for two hours, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (134 mg, 1.10 mmoL) and DBU (168 mg, 1.10 mmoL). After stirring overnight at rt, the THF was removed by rotary evaporation. The residue was dissolved in water and IN HCl was added until the pH = 5. This aqueous solution was extracted with EtOAc (3x). The combined EtOAc extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by flash column, eluting with 3percent methanol in methylene chloride, gave 300 mg (53percent) of (15, AR, 65, 145, 18R)- [1-cis-A-Cyclopropanesulfonylaminocarbonyl- 12-cyclopropyl- 18-(tert- butyldimethylsilyloxy)-2,15-dioxo-3,12,16-triaza-tricyclo[14.3.0.04’6]nonadec-7-en- 14-yl]carbamic acid, tert-butyl ester as a white solid: LC-MS (Phenomenex 10 mum Cl 8 HPLC column: 3.0×50 mm length. Gradient: 100percent Solvent A/0percent Solvent B to 0percent Solvent A/100percent Solvent B. Gradient time: 2 min. Hold time: 1 min. Flow rate: 5 mL/min. Detector Wavelength: 220 nM. Solvent A: 10percent MeOH / 90percent H2O / 0.1percent TFA. Solvent B: 10percent H2O / 90percent MeOH / 0.1percent TFA.) (Retention time: 2.40 min), MS m/z 724 (M++l).

The synthetic route of 154350-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64057; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 7223-30-5, 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. 7223-30-5 name is 3-Phenylpropiolamide, 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.

General procedure: A degassed solution of 3-phenylpropiolamide (5.0 mmol) and N,N-dimethylethane-1,2-diamine (5.0mmol) in DMF (6.0 mL) was added through canula to a degassed solution of thevinyl iodide (1.0 mmol), Cs2CO3 (5.0 mmol) and CuI (2.0mmol) in DMF (25.0 mL) at 23 C. After stirring for the indicated time, thereaction was quenched with water and extracted with EtOAc (x3). The combined organic layers were washedwith brine, dried over Na2SO4 and filtered. The solventwas concentrated under reduced pressure, and the residue was purified byflash chromatography as indicated.

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

Reference:
Article; Garcia-Rodriguez, Jose; Mendiratta, Saurabh; White, Michael A.; Xie, Xiao-Song; De Brabander, Jef K.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4393 – 4398;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 631-58-3, A common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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.

A mixture of propanethioamide ethyl] amino-i -oxo-3 -phenylpropane-2-ylcarbamate (12): A mixture of propanethioamide(69 mg, 0.78 mmol) and (5)-tert-butyl 4-bromo-i-(4-nitrophenyl)-3-oxobutan-2- ylcarbamate, 7, (0.300 g, 0.77 mmol) in CH3CN (4 mL) is refluxed for 2 hours. The reaction mixture is cooled to room temperature and diethyl ether is added to precipitate the intermediate 2-(nitrophenyl)-(5)- 1 -(4-ethylthiazol-2-yl)ethylamine which is isolated by filtration as the hydrobromide salt. The hydrobromide salt is dissolved in DMF (8mL) together with diisoproylethylamine (0.38 mL, 2.13 mmol), i-hydroxybenzotriazole (107 mg, 0.71 mmol) and (5)-(2-methoxycarbonyl-amino)-3-phenylpropionic acid (175 mg, 0.78 mmol). The mixture is stirred at 0 C for 30 minutes then at room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combined organic phase is washed with 1 N aqueous HC1, 5 % aqueous NaHCO3, water and brine, and dried over Na2SO4. The solvent is removed in vacuo to afford 0.300g (81% yield) of the desired product which is used without further purification. LC/MSESI+MS 483 (M+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:
Patent; AERPIO THERAPEUTICS INC.; PETERS, Kevin; SHALWITZ, Robert; JANUSZ, John; SMITH, Alexander; WO2014/145068; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H17ClN2O3

(Step 1) A solution of the compound (0.300 g) obtained in Example 29, step 1, 2,5-dimethylpyrrolidine (258.0 muL) and tBuONa (0.152 g) in DME (2 mL) was degassed with argon gas, 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene-(allyl)-palladium(2)-chloride (0.051 g) was added, and the mixture was refluxed under argon atmosphere for 2 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with water and brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?35% ethyl acetate/hexane) and basic silica gel column chromatography (solvent gradient; 0?35% ethyl acetate/hexane) to give tert-butyl 8-(2,5-dimethylpyrrolidin-1-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.314 g, 86%) as a colorless oil. 1H-NMR(CDCl3): delta 1.29(6H,d,J=6.4Hz), 1.43(9H,s), 1.60-1.75(2H,m), 1.95-2.10(2H,m), 3.77(2H,t like), 4.09(2H,brs like), 4.19-4.40(4H,m), 6.06(1H,d,J=8.3Hz), 7.20-7.40(1H,m)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 956434-30-3.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 37394-93-7, These common heterocyclic compound, 37394-93-7, name is 2-Chloro-N-(o-tolyl)acetamide, 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.

Chrysin (1) (50 mg, 0.20 mmol), 2-chloro-N-(o-tolyl)acetamide (3) (38 mg, 0.21 mmol) andanhydrous potassium carbonate (56 mg, 0.41 mmol) were dissolved in DMF (2 mL). The reactionmixture was stirred at 80 C for 61 h, then, it was evaporated under reduced pressure. Water (30 mL)was added to the residue and it was extracted with DCM (30 mL). Then, saturated NaCl solution (20mL) was added to the aqueous phase and it was extracted with DCM (2 x 20 mL). The combinedorganic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified withpreparative TLC (DCM : MeOH = 40 : 1) to give 31 mg (46 %) of compound 13 as a yellow solid. M.p.:220-221 C. TLC (DCM : MeOH = 40 : 1); Rf = 0.69.

Statistics shows that 2-Chloro-N-(o-tolyl)acetamide is playing an increasingly important role. we look forward to future research findings about 37394-93-7.

Reference:
Article; Mayer, Szabolcs; Keglevich, Peter; Abranyi-Balogh, Peter; Szigetvari, Aron; Dekany, Miklos; Szantay, Csaba; Hazai, Laszlo; Molecules; vol. 25; 4; (2020);,
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 5338-44-3 as follows. Application In Synthesis of Ethyl 4-acetamidobenzoate

General procedure: Phosphorus oxychloride, 4.8 mL (7.7 g, 50 mmol) and 1.3 g (20 mmol) of NaN3 were added to a vigorously stirred solution of amide 2a-2e, 6, 11a-11e, 15, 19a, 19b, 22, 25a, 25b, or 27 (10 mmol) in 20 mL of acetonitrile. The mixture was refulxed for 5-7 h, acetonitrile was evaporated, the residue was dissolved in water with ice, and the solution was neutralized with saturated soda solution. The precipitate that formed was filtered off. Liquid tetrazoles were extracted with methylene chloride, and the solvent was evaporated in a vacuum.

According to the analysis of related databases, 5338-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Obushak, M. D.; Pokhodylo, N. T.; Shyyka, O. Ya.; Russian Journal of Organic Chemistry; vol. 56; 5; (2020); p. 802 – 812; Zh. Org. Khim.; vol. 56; 5; (2020); p. 753 – 765,13;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 445-28-3, name is 2-Fluorobenzamide, molecular formula is C7H6FNO, 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. HPLC of Formula: C7H6FNO

A 2 liter 3-neck round bottom flask was charged with 100 g 2-fluorobenzamide (0.719 mol, 1 eq.). An inert atmosphere was introduced by two vacuum/argon cycles. 863 mL IM Meerwein’s/CH2Cl2 solution (0.863 mol, 1.2 eq.) was then added to the flask via canula under N2 pressure, giving initially a slurry which became a clear solution after ~ 30 minutes. After ~ 4 hours stirring at 23 0C under argon, a slurry was again present. The mixture was stirred for a total of 16 hours at 23 0C under argon, then it was poured quickly into a large flask and the CH2Cl2 removed at the rotovap, giving an off-white solid. This solid was then suspended in 250 rnL EtOAc, heated briefly at reflux (~ 30 seconds), then the resultant slurry was filtered while still warm under N2 on a corase- fritted funnel. After drying on the frit under a vigorous flow of N2 for one hour, 155 g 2- fluorobenzimidate 5 (84%) was obtained as a colorless solid. It was immediately bottled and placed in a desiccator. M.p. 128-1310C; 19F NMR (DMSO) delta: -113.8, -154.2 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 445-28-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/67218; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 640-61-9, name is N,4-Dimethylbenzenesulfonamide, 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 640-61-9, Product Details of 640-61-9

The reaction mixture, which was prepared from Bromoethynylbenzene (1.38 g, 7.31mmol), N-Methyl-p-toluenesulfonamide (1.23 g, 6.65 mmol), K2CO3 (1.83 g, 13.3mmol), CuSO4?5H2O (0.17 g, 0.66 mmol) and 1,10-Phenanthroline (0.24 g, 1.33mmol) in Toluene (8 mL), was stirred at 60 C for 40 h. After cooled to rt, the resulting mixture was filtered on celite, and the volatiles were removed under reduce pressure. The residue was separated by column chromatograpy on silica gel(Hexane/EtOAc = 3:1) to provide 1f (1.74 g, 92%). IR (KBr) nu 2233, 1339, 1189 cm-1; 1H NMR (400 MHz, CDCl3) delta 2.46 (s, 3H), 3.15(s, 3H), 7.07-7.32 (m, 3H), 7.32-7.64 (m, 4H) 7.84 (d, J = 8.2 Hz, 2H); 13C NMR(100 MHz, CDCl3) delta 21.6, 39.2, 68.9, 83.9, 122.6, 127.7, 127.8, 128.2, 129.7, 131.3,133.1, 144.8; EI-LRMS m/z 285 (M+), 130, 105, 89; EI-HRMS m/z calcd for C16H15NO2S (M+) 285.0823, found 285.0817.

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, N,4-Dimethylbenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wakamatsu, Hideaki; Yanagisawa, Rika; Kimura, Sho; Osawa, Nao; Natori, Yoshihiro; Yoshimura, Yuichi; Synlett; vol. 28; 16; (2017); p. 2135 – 2138;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common compound: 627-12-3, name is Propyl carbamate, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 627-12-3

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 × 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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, 627-12-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics