Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 120157-96-2, name is Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate, 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 120157-96-2, category: amides-buliding-blocks

Reference Example 63 tert-Butyl 4-hydroxymethylbenzylcarbamate Diisobutylaluminum hydride (25.7 ml, 0.93 M hexane solution) was added dropwise to a THF solution (40 ml) of methyl 4-[N-(tert–butoxycarbonyl)aminomethyl]benzoate (2.54 g) at -78C, followed by stirring at the same temperature for 2 hours. A saturated aqueous ammonium chloride solution (10 ml) and diethyl ether were added dropwise to the reaction solution, followed by stirring at room temperature for 1 hour. Magnesium sulfate was added to the reaction solution, followed by further stirring for 1 hour. After removal of the resulting precipitate by filtration trough celite, the filtrate was concentrated, the thus obtained residue was purified by silica gel column chromatography, and the title compound (1.22 g) was obtained as a colorless oil from the fraction of the elude of n-hexane: ethyl acetate = 10:3. 1H-NMR (400 MHz, CDCl3) delta: 1.43 (9H, s), 4.29 (2H, d, J=5.6 Hz), 4.67 (2H, d, J=5.9 Hz), 4.87 (1H, bs), 7.25 (2H, d, J=8.1 Hz), 7.32 (2H, d, J=8.1 Hz).

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 152192-95-5, These common heterocyclic compound, 152192-95-5, name is tert-Butyl ethyl(2-hydroxyethyl)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.

Stage 2: [2-(1,3-Dihydroisoindol-2-yl)ethyl]ethylcarbamic acid tert-butyl ester: A solution of 10.2 g of diethyl azodicarboxylate in 60 ml of THF is added dropwise to a mixture containing 11.92 g of ethyl-(2-hydroxyethyl)carbamic acid tert-butyl ester, 15.2 g of isoindole-1,3-dione and 8.6 g of triphenylphosphine in 40 ml of THF. The medium is kept stirring overnight at room temperature and then concentrated to dryness. The medium is taken up in 100 ml of ethyl ether, the precipitate formed is removed by filtration. The filtrate is concentrated and chromatographed on a silica column (heptane in a gradient up to 3% ethyl acetate). 14 g of expected product are obtained.

Statistics shows that tert-Butyl ethyl(2-hydroxyethyl)carbamate is playing an increasingly important role. we look forward to future research findings about 152192-95-5.

Reference:
Patent; sanofi-aventis; US2008/269170; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 116861-31-5, These common heterocyclic compound, 116861-31-5, name is tert-Butyl (3-chloropropyl)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.

S1-1 (557 mg, 2.876 mmole, 1 equiv) was dissolved in 2 mL dry DMF under inert atmosphere. To this solution, potassium thioacetate (548 mg, 3.164 mmole, 1.1 equiv) was added as a powder to the stirring reaction mixture. The reaction was allowed to go overnight and monitored for completion by TLC and LC/MS. The reaction mixture was diluted with 20 mL EtOAc and transferred to a seperatory funnel. The organic layer was washed with 3 X 20 mL saturated NaCl solution. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness to afford a crude yellow oil (MW: 233.33 g/mol, 400 mg, 60% yield), which was of sufficient purity for the next step.1H NMR (400 MHz, CDCl3): 3.12 (m, 2H), 2.86 (t, J = 7.0 Hz, 2H), 2.3 (s, 3H), 1.71 (m, 2H), 1.40 (s, 9H).

The synthetic route of 116861-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHOKAT, Kevan, M.; GENTILE, Daniel; MOSS, Steven; (380 pag.)WO2018/112420; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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: C6H13NO2

24 g (120 mmol) of 2-chloro-5-(trifluoromethoxy)pyridine, 19.1 g (150 mmol) of tert-butyl N-methylcarbamate and 17.5 g (180 mmol) of sodium tert-butoxide were dissolved in 400 ml of toluene, 2.8 g (3 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 1.73 g (3 mmol) of Xantphos were added under argon, and the mixture was stirred at 100-105 C. for 12 h. Subsequently, the mixture was filtered through Celite and the solvent was distilled off under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16066-84-5, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; HAGER, Dominik; HOFFMEISTER, Laura; KAUSCH-BUSIES, Nina; WILCKE, David; WILLOT, Matthieu; GOeRGENS, Urich; ILG, Kerstin; MOSRIN, Marc; PORTZ, Daniela; TURBERG, Andreas; US2018/305353; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1314538-55-0, 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. 1314538-55-0 name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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.

A mixture of 4,6-dichloro-2-(trifluoromethyl)pyrimidine (500 mg, 2.30 mmol, 1.00 equiv), potassium terf-butyl N-[(trifluoroboranuidyl)methyl]carbamate (546 mg, 2.30 mmol, 0.99 equiv), Pd(PPh3)2Cl2 (162 mg, 0.23 mmol, 0.10 equiv), and sodium carbonate (488 mg, 4.60 mmol, 1.99 equiv) in t-butanol (10 mL)/water (2 mL) was stirred for 2 h at 70 C under nitrogen. The solid was filtered off and the filtrate was diluted with water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1/5) to afford the title compound (450 mg, 63%) as a white solid. LCMS [M+H+] 312

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; VERMA, Vishal; SHORE, Daniel; VOLGRAF, Matthew; ESTRADA, Anthony A.; LYSSIKATOS, Joseph; (153 pag.)WO2018/15410; (2018); 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. 113778-69-1, name is N-Methoxy-N-methylisobutyramide, A new synthetic method of this compound is introduced below., Product Details of 113778-69-1

A 250 mL flask was charged with a solution of 2-chloro-6-methoxypyridine (20 g, 0.139 mol, 1 equiv.) in THF (300 mL) under nitrogen atmosphere. To the mixture was then added tert-butyllithium (131 mL, 0.210 mol, 1.5 equiv.), which was added dropwise with stirring at -70 C. The reaction mixture was stirred at -78 C. for 2 h. N-methoxy-N-methylisobutyramide (24 g, 0.182 mol, 1.3 equiv.) was then added dropwise. The mixture was stirred for 3.0 h at -78 C. The reaction progress was monitored by LCMS. The reaction was quenched by the addition of ammonium chloride aqueous solution and then extracted with ethyl acetate, the organic layers combined and concentrated under vacuum. The residue was applied onto a sillia gel column with PE/EA=100/1 to yield 1-(6-chloro-2-methoxypyridin-3-yl)-2-methylpropan-1-one as yellow oil. Mass spectrum (ESI, m/z): Calculated for C10H12ClNO2, 214.1 (M+H), found 214.1.

The synthetic route of 113778-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 144-80-9, 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 144-80-9 as follows.

Example 155N-({4-[(4-[difluoro(4-fluorophenyl)methyl]-6-{[6-(ethyloxy)-1,3-benzothiazol-2-yl]amino}-2-pyrimidinyl)amino]phenyl}sulfonyl)acetamideA mixture of N-{2-chloro-6-[difluoro(4-fluorophenyl)methyl]-4-pyrimidinyl}-6-(ethyloxy)-1,3-benzothiazol-2-amine (100mg, 0.222mmol), N-[(4-aminophenyl)sulfonyl]acetamide (95mg, 0.444mmol) and 4-toluenesulfonic acid monohydrate (50.6mg, 0.266mmol) in acetonitrile (3m L) was sealed and heated at 1200C for 4 hours in a Biotage “Initiator” microwave. The product was purified by mass-directed autopreparative HPLC (formic acid modifier) to afford the title compound (21 rmg, 0.033mmol, 20% yield) as a white solid. LCMS (Method A): Rt 1.19 minutes; m/z 629 (MH+).

According to the analysis of related databases, 144-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; ALDER, Catherine, Mary; BALDWIN, Ian, Robert; BARTON, Nicholas, Paul; CAMPBELL, Amanda, Jennifer; CHAMPIGNY, Aurelie, Cecile; HARLING, John, David; MAXWELL, Aoife, Caitriona; SIMPSON, Juliet, Kay; SMITH, Ian, Edward, David; TAME, Christopher, John; WILSON, Caroline; WOOLVEN, James, Michael; WO2010/106016; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 90-16-4,Some common heterocyclic compound, 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, molecular formula is C7H5N3O, 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: A suspension of 1,2,3-benzotriazin-4-one (II, 6 mmol), dibromoalkane (30 mmol), and potassium carbonate (1.66 g, 12 mmol) in acetone (50 mL) was refluxed for 8 h, and then cooled to room temperature. After removal of acetone by evaporation under reduced pressure, the residue was washed with water (100 mL) and extracted with CH2Cl2 (80 mL × 2). The organic layer was dried over anhydrous Na2SO4, concentrated and purified by flash chromatography on silica gel, eluting with petroleum ether (60-90 C)/EtOAc to afford 3-bromoalkyl-1,2,3-benzotriazin-4-one III in yields of 46-62%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Benzo[d][1,2,3]triazin-4(3H)-one, its application will become more common.

Reference:
Article; Zhang, Fan; Wu, Dang; Wang, Gao-Lei; Hou, Shuang; Ou-Yang, Ping; Huang, Jin; Xu, Xiao-Yong; Chinese Chemical Letters; vol. 28; 5; (2017); p. 1044 – 1048;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 198989-07-0, These common heterocyclic compound, 198989-07-0, name is tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, 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 825-[2-(2-Chloro-phenyl)-l-methyl-ethyl]-2,5-diaza-bicyclo[2.2.1]heptane-2- carboxylic acid (4-trifluoromethyl-phenyl)-amide (METHOD A)(i) l-Isocyanato-4-trifluoromethyl-benzene (990mg, 5.29mmol) was added to a stirred solution of 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (Ig, 5.04mmol) in dichloromethane (DCM) (20ml) and stirred overnight at room temperature. Trifluoroacetic acid (4ml) was added and stirred for 2h. The solution was made basic with 2N sodium hydroxide solution, separated, extracted with DCM and the combined organic extracts dried and evaporated. The residue was loaded onto a flash silica column, eluted with ethyl acetate to remove impurities followed by methanol/DCM (1:9) to elute the product. Evaporation gave 2,5-Diaza- bicyclo[2.2. lJheptane-2-carboxylic acid (4-trifluoromethyl-phenyl)-amide (905mg) as a brown solid.

Statistics shows that tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 198989-07-0.

Reference:
Patent; VERNALIS (R & D) LIMITED; WO2007/7069; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 154350-29-5, name is Cyclopropanesulfonamide, 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 154350-29-5, Computed Properties of C3H7NO2S

Example 73Cyclopropanesulfonic acid [3,3-dimethyl-2-(4-morpholin-4-yl-phenyl)-l,2,3,4- tetrahydro-quinoline-6-carbonyl] -amideA mixture of 3,3-dimethyl-2-(4-morpholin-4-yl-phenyl)-l,2,3,4-tetrahydro-quinoline-6- carboxylic acid (70 mg, 0.19 mmol), l-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (55 mg, 0.29 mmol), 4-dimethylaminopyridine (35 mg, 0.29 mmol), cyclopropane sulfonamide (69 mg, 0.57 mmol) in dichloromethane (10 mL) was heated for at 65 °C for 12 hours. Removal of the solvent afforded an oil residue. Purification by Waters automated flash system (column: Xterra 30 mm x 100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1percent formic acid in water) afforded cyclopropanesulfonic acid [3,3-dimethyl-2-(4-morpholin-4-yl- phenyl)-l,2,3,4-tetrahydro-quinoline-6-carbonyl] -amide (24 mg, 27percent) as a light yellow solid: LC/MS m/e calcd for C25H31N3O4S (M+H)+: 470.6, observed: 470.3.

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, Cyclopropanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; WU, Jim, Zhen; ZHOU, Mingwei; WO2011/128251; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics