Tag: M.W=100-200

Synthetic Route of 1520-70-3,Some common heterocyclic compound, 1520-70-3, name is Ethanesulfonamide, molecular formula is C2H7NO2S, 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 solution of free acid (50 mg, 0.11 mmol) from Example 226 in 1 ML of methylene chloride was added ethyl sulfonamide (18 mg, 0.17 mmol), EDAC (25 mg, 0.13 mmol), and DAMP (2.7 mg, 0.022 mmol) sequentially.The mixture was stirred at ambient temperature for 16 h.The solvent was then removed on a rotavap under reduced pressure and the residue was purified on an Alltech sep-pak, eluding with 1percent MeOH in EtOAc to give 30 mg (50percent yield) of the title compound as a light yellow solid. 1H NMR (CDCl3, 300 MHz) delta 1.18 (d, J=6.3 Hz, 6H), 1.34 (t, J=7.5 Hz, 3H), 1.61-1.74 (m, 2H), 1.84-2.04 (m, 1H), 2.13-2.35 (m, 1H), 2.60-2.75 (m, 2H), 3.44 (p, J=7.5 Hz, 2H), 3.53-3.66 (m, 1H), 3.66-3.85 (m, 2H), 4.00-4.18 (m, 1H), 6.71 (d, J=8.7 Hz, 1H), 6.88 (d, J=15.6 Hz, 1H), 7.31 (dd, J=2.4, 8.4 Hz, 1H), 7.41 (d, J=1.8, 8.4 Hz, 1H), 7.51 (d, J=1.8 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.67 (d, J=15.6 Hz, 1H), 8.43 (s, 1H). MS (ESI+) (M+H)+ at m/z 546.

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

Reference:
Patent; Abbott Laboratories; US2004/116518; (2004); 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. 98-18-0, name is 3-Aminobenzenesulfonamide, A new synthetic method of this compound is introduced below., name: 3-Aminobenzenesulfonamide

A solution of 1-(2-methylsulfonyl-pyrimidin-4-yl)-1H-indazole (100 mg, 0.36 mmol) and p-toluenesulfonic acid (139 mg, 0.73 mmol) in i-PrOH (4 ml) was treated with 3-aminobenzene-sulfonamide (251 mg, 1.46 mmol) in a microwave synthesizer at 150° C. for 20 min. The mixture was partitioned between water and ethyl acetate, the organic layer separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was absorbed on silica gel and purified by flash chromatography (EtOAc/hexane, gradient from 30:70 to 50:50) to afford the title compound. This residue was triturated with aqueous NaOH (1 M), the solid collected by filtration, washed with water and dried under vacuum to afford 3-(4-indazol-1-ylpyrimidin-2-ylamino)-benzenesulfonamide (50 mg, 37percent yield). MS=367 [M+H]+.

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; Roche Palo Alto LLC; US2008/146565; (2008); A1;,
Amide – Wikipedia,
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Application of 445-28-3, 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 445-28-3 as follows.

o-fluorobenzamide (27.88,0.2mol), high purity KOH 1(22.48,0.4 mol), Methanol (12.88,0.4 mol), DMS0 (200 mL) was added to the reactor and the reaction was stirred at 20 C for 16 hours. After completion of the reaction, 800 mL of ethyl acetate was added to the system and diluted 5 times with 200 mL of saturated brine. The organic phase was separated, dried over anhydrous sodium sulfate, filtered, evaporated to dryness, and then it was loaded onto a silica gel column to separate petroleum ether: ethyl acetate = 4: 1 (volume ratio) As eluent until the product is present, the solution containing the product is collected by steaming and evaporated to dryness, followed by drying with a vacuum chestnut to give pure o-methoxybenzamide in 80% yield.

According to the analysis of related databases, 445-28-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ferguson (Wuhan) Biotech Company Limited; Su, ji; Hua, Rui Mao; Ouyang, Kang Le; (6 pag.)CN106565522; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 147751-16-4, These common heterocyclic compound, 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, 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 l-L flask was charged with 2-(diethoxyphosphorylmethyl)-4-iodo-l- methoxy -benzene (5.0 g, 13 mmol), /e/V-butyl -methylsulfonylcarbamate (7.1 g, 36 mmol), cuprous iodide (2.5 g, 13 mmol), /VJV-dimethylglycine (1.4 g, 13 mmol) and potassium phosphate tribasic (11.4 g, 52.1 mmol) and the flask was purged with nitrogen. NN- Dimethylacetamide (43 mL) was then added and the flask was purged with nitrogen again, and an empty balloon was placed on top of the reaction vessel to allow room for gas generation. The reaction was stirred at 110 C for 16 hours. The resulting mixture was diluted with 10% glycine in water and acidified to pH 1 with 1N HC1, extracted with dichloromethane (3 x 50 mL), dried with anhydrous MgS04, concentrated under reduced pressure and purified by silica gel column chromatography (0% to 10% methanol in dichloromethane) to give the title compound as a white solid (922 mg, 20% yield). LCMS (ESI+) m/z 352 (M+H)+

The synthetic route of 147751-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
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Application of 183059-24-7, 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. 183059-24-7 name is tert-Butyl 2-hydroxy-2-methylpropylcarbamate, 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.

2,2-dimethyloxirane (0.1 g, 1.388 mmol) was added dropwise to 20 mL icecooled solution of ammonium hydroxide. The reaction mixture was stirred for 12 hours at roomtemperature. The solvent was removed under vacuum and the residue was dissolved inmethanol. Di-tert-butyl dicarbonate (0.75 g, 3.47 mmol) was added to the reaction mixture and15 stirred for 4 hours. The mixture was purified using column chromatography (24%EtOAc/hexane) to obtain tert-butyl 2-hydroxy-2-methylpropylcarbamate. The pure tert-butyl 2-hydroxy-2-methylpropylcarbamate was dissolved in 5 mL of trifluoroacetic acid and stirred for35 minutes. The solvent was removed under reduced pressure to afford 1-amino-2-methylpropan-2-ol as the trifluoroacetate salt 1′. 1H NMR 500 MHz (500 MHz, CDC13, 8 in20 ppm): 8 8.62 (s, 2H), 3.02 (d, 2H), 2.06-2.04 (m, 2H), 1.37-1.34 (s, 6H).

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

Reference:
Patent; PURDUE RESEARCH FOUNDATION; ENDOCYTE, INC.; LOW, Philip Stewart; WANG, Bingbing; LEAMON, Christopher Paul; LU, Yingjuan J.; WHEELER II, Leroy W.; (102 pag.)WO2017/205661; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 37045-73-1, name is 3-(Methylsulfonamido)aniline, molecular formula is C7H10N2O2S, 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. Quality Control of 3-(Methylsulfonamido)aniline

Take a 25 mL Schlenk reaction tube, add 74 mg of 3-methanesulfonylaminoaniline, 9 mg of palladium acetate and 80 mg of molecular sieve.93 mg of ethyl 2-oxopropionate, 96 mg of acetic acid and 2 mL of dimethyl sulfoxide were injected, followed by a 200 mL oxygen balloon, and stirred at 70 C for 18 hours.After the reaction was completed, 15 mL of ethyl acetate was added to dilute the reaction mixture, and the filtrate was washed twice with 10 mL of brine, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate. The organic phase was combined and purified by column chromatographyof Ethyl 6-Methanesulfonylamino-1H-indole-2-carboxylate pure product 78mg, yield 69%; ethyl 4-methanesulfonylamino-1H-indole-2-carboxylate pure product 1mg, yield 1 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37045-73-1, its application will become more common.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xiao Zhiyan; Ren Long; Tang Yanbo; Yang Ying; (27 pag.)CN109748840; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)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 57561-39-4, HPLC of Formula: C8H17NO3

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-IH-pyrazole (3.964 g, 20.43 mmol), DIAD (4.42 mL,22.47 mmol), triphenylphosphine (5.89 g, 22.47 mmol) and tert-butyl (2-hydroxyethyl)(methyl)carbamate (for a preparation see Intermediate 134, 3.58 g, 20.43 mmol) were dissolved in THF at 0 C under nitrogen for 48 h. The reaction mixture was concentrated and the orange oil triturated with diethyl ether. The precipitated solid was removed by filtration and washedwith more diethyl ether. The filtrate was concentrated to give 12.45 g of crude thick orange oil. This was purified by chromatography on silica (220 g cartridge, eluting with 0-100% ethyl acetate/cyclohexane over 13 CVs, collecting all fractions). Product fractions were combined to give the product (4.29 g, 12.21 mmol, 59.8%) as a yellow oil.LCMS (2 mm Formic): Rt = 1.07 mi [MH] = 352.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)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 389890-43-1, Application In Synthesis of tert-Butyl (cis-3-hydroxycyclobutyl)carbamate

In a round-bottomed flask charged with tert-butyl(cis-3-hydroxycyclobutyl)carbamate (1.11 g, 5.93 mmol) and triethylamine (2.474 ml, 17.79 mmol) was added CH2Cl2 (12 ml). methanesulfonyl chloride (0.505 ml, 6.52 mmol) was added dropwise via syringe at -20 C. over 5 min. The reaction mixture was stirred at room temperature for 30 min, then diluted with water (15 mL) and extracted with CH2Cl2(2*). The organic extract was washed with saturated NH4Cl and dried over MgSO4. It was filtered and concentrated in vacuo to give cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (1.64 g, 6.1 mmol, 100% yield) as a off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 513-74-6, name is Ammonium carbamodithioate, 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 513-74-6, Safety of Ammonium carbamodithioate

Step 89.2: Ammonium dithiocarbamate (208 mg, 1.89 mmol) and 72 (X = Br) (200 mg, 0.63 mmol) in anhydrous MeOH (10 mL) was stirred for 10 mins. The resulting cream precipitate was collected by filtration, resuspended in acetic acid (10 mL) and refluxed for 1 hr. The reaction was cooled to room temperature and diluted with ice cold water. The resulting green precipitate was collected by filtration, redissolved in (CH2CI2:Me0H 95:5, 100 mL) and dried (Na2SO4). The pale green solution was concentrated in vacuo to give 4-(5-bromopyrazolo[1 ,5-a]pyridin-3-yl)thiazole-2(3/-/)-thione (73: X = Br) (136 mg, 70 percent) that is stored in the freezer. 1H NMR delta (400 MHz, d6-DMSO) 13.59 (br s, 1 H), 8.74 (d, J 7.3 Hz, 1H1), 8.51 ( s, 1 H ), 8.22 (d, J 1.8 Hz, 1H), 7.27 (s, 1 H1), 7.19 (dd, J 7.3, 2.1 Hz, 1 H). LCMS (APCI+) 312 (MH+ with 79Br, 100percent), 314 (MH+ with 81Br, 100percent).

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

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2009/8748; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 7223-30-5, The chemical industry reduces the impact on the environment during synthesis 7223-30-5, name is 3-Phenylpropiolamide, I believe this compound will play a more active role in future production and life.

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.

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

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