Month: March 2021

Application of 1943-79-9,Some common heterocyclic compound, 1943-79-9, name is Phenyl methylcarbamate, molecular formula is C8H9NO2, 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 solution of (2R,4S,4aS)-8-amino-2,4-dimethyl-l,2,4,4a-tetrahydro-2’H,6H-spiro[l,4- oxazino[4,3-a]quinoline-5,5′-pyrimidine]-2′,4′,6′(leta,3eta)-trione (Intermediate 34, 250 mg, 0.74 mmol) in anhydrous THF (20 mL) at 0 0C was added triethylamine (2.5 g, 0.024 mol) followed by methylphenoxycarbamate (0.66 mmol) and the mixture was refluxed for 48 hours. Methyl phenoxy carbamate was prepared by stirring methyl amine (1 eq.) and phenylchloro formate (1 eq.) in DCM at -30 0C to room temperature for 4 hours, and was purified by column chromatography. The reaction mixture was quenched with HCl (IN, 30 ml) and extracted with ethyl acetate (5 x 20 mL). The organic phase was dried over anhydrous sodium sulphate and was concentrated under reduced pressure. The residue thus obtained was washed with ether and further purified by preparative TLC to give the title compound. Yield: 20 mg (70%). MS(ES) MH+: 402.2 for Ci9H23N5O5 1H NMR (400 MHz, DMSO-d6) delta : 0.9 (d, 3H), 1.1 (d, 3H), 2.5 (d, 3H), 2.9 (d, IH), 3.1 (d, IH), 3.5 (d, IH), 3.55 (m, 2H), 3.85 (d, IH), 5.8 (m, IH), 6.7 (d, IH), 6.9 (s, IH), 7.1 (d, IH), 11.7 (bs, 2H).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/4382; (2009); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6292-59-7, 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 6292-59-7 as follows.

Step-4:Preparation of 4-(14-dimethylethyl)-N-[6-chloro-5-(2-methoxyphenoxy)[2,2′-bipyrimidin]-4- yl|benzenesulfonamide (VII).5-(2-Methoxyphenoxy)-2-(pyrimidin-2-yl)-tetrahydropyrimidin-4,6-dione (IV) (10Og,320.22mmol) was added to phosphorous oxychloride (196.4g). The resulting reaction mass was slowly heated to 103-1050C and stirred for 4 hrs. The reaction mass was added to a mixture of toluene (450ml) and water (350ml) at 20-500C and treated with 30percent w/w aqueous sodium hydroxide solution (271.5ml) at 70-800C. The organic layer was separated and treated with activated carbon (7g) at 80-900C for 30min, filtered through hyflo and washed with hot toluene (300ml). 4-(l ,l-Dimethylethyl)benzene sulfonamide (VI) (68.3g, 320.2mmol) was added to the filtrate, followed by potassium carbonate (53.03g, 384.27 mmol) and tetrabutylammonium bromide (3.19g, 9.59 mmol) were added, heated to reflux temperature and separated water azeotropically for 2 hrs, the reaction mass was cooled to 20-250C, filtered the solid and dried. Further, the solid was added to DM water and acidified to pH 0.5 to 0.7 with hydrochloric acid. The solid was filtered washed with DM water and dried to yield 144.5g of title product.Chromatographic purity: 97.92percent (by HPLC, by area normalization)

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AUROBINDO PHARMA LIMITED; BRAJESH, Kumar, Sinha; KONDURU, Rajasekhara, Raju; BUDIDET, Shankar, Reddy; VADDI, Pandu, RangaRao; AMINUL, Islam; MEENAKSHISUNDERAM, Sivakumaran; WO2011/24056; (2011); A2;,
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. 6269-91-6, name is 2-Methyl-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8N2O4S

To a solution of 3-aminosulfonyl-4-methylnitrobenzene in dichloromethane and methanol was added 10percent Pd/C and the mixture shaken under a hydrogen atmosphere at 50 psi for 15 minutes.The mixture was filtered through diatomaceous earth and the filter cake was washed with methanol.The combined organic solvents were concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 3-aminosulfonyl-4-methylaniline, LCMS: purity: 87percent; MS (m/e): 187 (MH+).

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 6269-91-6.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; US2012/232106; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, A new synthetic method of this compound is introduced below., SDS of cas: 75175-77-8

General procedure: With a mixture of N,N-Dimethylenaminones 1 (1.0 mmol), isatins 2 (0.5 mmol), ammonium acetate 3 (1.0 mmol) in AcOH (1 mL) and EtOH-water (1:4) (5 mL), the reaction mixture was stirred at 80 C for 6 h until TLC indicated that the reaction was completed. The reaction mixture was allowed to cool to room temperature, neutralised with a saturated solution of Na2CO3 to pH 8-9, and then was extracted with ethyl acetate (2 ¡Á 30 mL). The organic phase was washed with water (20 mL) and the organic layer dried over Na2SO4, and concentrated under reduced pressure. The crude product was chromatographed onsilica gel (200-300 mesh) using a mixture of petroleum ether and ethyl acetate as eluent to afford the product 4.

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; Zhou, Pan; Hu, Biao; Lu, Lingling; Huang, Rong; Yu, Fuchao; Journal of Chemical Research; vol. 41; 9; (2017); p. 513 – 516;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, 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: C8H6FNO2

To a stirred solution of step 2 intermediate (2.7 g, 16.157 mmol) in sulphuric acid (3 ml) a mixture of nitric acid (69 %, 0.72 ml, 16.157 mmol) and concentrated sulphuric acid (2 ml) was drop wise added at 0 C under nitrogen atmosphere. The reaction mixture was stirred at 0 C for 30 min. The reaction mixture was quenched with ice-cooled water and solid was precipitated. The precipitated solid was dissolved in ethyl acetate (30 ml) and washed with aqueous saturated solution of sodium bicarbonate (150 ml). The ethyl acetate layer was dried and filtered and dried (Na2S04) and concentrated to yield 2.6 g of product as yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 4.79 (s, 2H), 7.26 (d, J = 12.0 Hz, 1H), 7.63 (d, / = 7.2 Hz, 1H), 1 1.03 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103361-99-5, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin Sundarlal; KUMAR, Sukeerthi; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; WO2013/153539; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 201162-53-0, These common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, 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 solution of tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate (1 g, 4.71 mmol, 1.00 equiv), potassium carbonate (1.3 g, 9.41 mmol, 2.00 equiv), 5-chloropyridin-2-carbonitrile (651 mg, 4.67 mmol, 1.00 equiv) in DMF (10 mL) was stirred for 2 h at 80 C. in an oil bath. The solids were filtered out. The resulting solution was extracted with 3*20 mL of ether and the organic layers combined. After concentration, the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (1:2) to afford 1 g (68%) of the title compound as a solid. LCMS (ESI, m/z): 315.17 [M+H]+

Statistics shows that 3-Boc-3,8-Diazabicyclo[3.2.1]octane is playing an increasingly important role. we look forward to future research findings about 201162-53-0.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1888-91-1, A common heterocyclic compound, 1888-91-1, name is N-Acetylcaprolactam, molecular formula is C8H13NO2, 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: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde(7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.

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; Antoniak, Damian; Sakowicz, Arkadiusz; Loska, Rafal; Makosza, Mieczyslaw; Synlett; vol. 25; 9; (2014);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6FNO2S

General procedure: A dry round bottom flask was cooled to rt under nitrogen, and was charged with Pd2(dba)3 (3.38mg, 0.0037mmol), cesium carbonate (361mg, 1.11mmol), and arenesulfonamide (69mg, 0.44mmol). Tertiary-butanol (2mL) was added, followed by ligand, xantphos (6.4mg, 0.011mmol) and 9-chloroacridine (80mg, 0.37mmol). The resulting suspension was stirred at rt for 5min, then heated to 80C for 12-17h. The reaction mixture was then cooled to rt and filtered through suction filtration. The organic fraction was evaporated, and the resulting residue was purified by silica gel chromatography with a hexane/Et-OAc as eluent (60:40).

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

Reference:
Article; Chourasiya, Sumit S.; Wani, Aabid A.; Nagaraja; Chakraborti, Asit K.; Bharatam, Prasad V.; Tetrahedron; vol. 74; 27; (2018); p. 3634 – 3641;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 37073-15-7, The chemical industry reduces the impact on the environment during synthesis 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, I believe this compound will play a more active role in future production and life.

A flame-dried, two necked, round bottomed flask was charged with methanesulfonyl benzotriazole (34b) (1.0 g, 0.005 mol), 2-furoic acid (0.57 g, 0.005 mol), dry triethylamine (2 ml_), and dry THF (20 ml_) under argon. The resulting solution was heated at reflux for 18 hours. After this time, the THF was removed under reduced pressure to afford a cream coloured residue, which was taken up in ethyl acetate and washed with 1 M HCI (3 chi 30 ml_). The ethyl acetate was dried (MgS04) and removed in vacuo to afford a white solid which was recrystallised from toluene to give the title compound (34c) as fluffy white crystals (0.82 g, 77.0 %); mp 171 – 172 C; Rf = 0.48 (DCM : petroleum ether, 5 : 5); Analysis Calcd. for Cn H7N302: C, 61.97; H, 3.31 ; N, 19.71 %. Found C, 61.73; H, 3.31 ; N, 19.71 %; vmax (KBr) / cm”1 3142 (NH), 1681 (C=0), 1556, 1447; deltaEta (d6-DMSO, 300 MHz) 8.30 (3H, m, H5, H8, H5), 8.08 (1 H, dd, 3. 4.= 3.8, Jy, v= 0.6, H3), 7.82 (1 H, td, J6, 5/ 7= 7.2, 6, 8= 1.2, H6), 7.65 (1 H, td, J7, 6/s=7.2, J7, 5= 1.2, H7), 6.94 (1 H, dd, 4. 3.= 3.8, 4. 5.= 1.8, H4); 5c(d6-DMSO, 75 MHz) 155.0 (CO), 150.8 (C5), 145.5 (C9), 144.4 (C2) 132.1 (C4), 131.3 (C6), 127.1 (C7), 125.4 (C3), 120.6 (C5 or C8), 114.7 (C5 or C8), 113.9 (C4).

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, 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF SUNDERLAND; TODD, Adam; ANDERSON, Rosaleen Joy; SMALL, David Antony Philip; GROUNDWATER, Paul William; BENTON, Matthew Richard; WO2014/96864; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, 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 19047-31-5, Computed Properties of C5H8ClNO

General procedure: To a solution of 5- bromine -2- chlorophenol (2.9g, 14.3mmol) in 50mL acetonitrile was added K2CO3 (2.5g,17.1mmol), and stirred for 30min intermediate product 10 was added and the solution was heated to 80C for 4h. The reaction solution was concentrated, water (100mL) was added, and extracted with EtOAc. The organic layer was collected and washed with water and brine for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford intermediate product 11.

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, 2-Chloro-N-cyclopropylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yan, Guoyi; Pu, Chunlan; Lan, Suke; Zhong, Xinxin; Zhou, Meng; Hou, Xueyan; Yang, Jie; Shan, Huifang; Zhao, Lifeng; Li, Rui; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 667 – 686;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics