Month: September 2021

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. 28797-48-0, name is 11-(2-Chloroacetyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 11-(2-Chloroacetyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one

EXAMPLE 7 5,11-Dihydro-11-[[[2-(1-ethyl-2-pyrrolidinyl)ethyl]amino]acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one Prepared analogously to Example 1 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 2-(2-aminoethyl)-1-ethylpyrrolidine. Yield: 9.5% of theory, Mp.: 109-111 C. (ethyl acetate/cyclohexane 2/1 v/v).

According to the analysis of related databases, 28797-48-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mihm; Gerhard; Eberlein; Wolfgang; Engel; Wolfhard; Trummlitz; Gunter; Mayer; Norbert; de Jonge; Adrian; Doods; Henri; US5002943; (1991); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)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 127828-22-2, HPLC of Formula: C9H20N2O3

To a stirred solution of 5g of 2-{(3-butynyl)-l-oxy}ethyl methanesulfonate and 5.32g of 2-[2-{2-(t-butoxycarbonyl)amino}ethyl-l- oxy]ethylamine in 60ml acetonitrile, was added drop-wise 3.6g of potassium carbonate dissolved in water at O0C. The reaction solution was allowed to slowly warm to RT and stirred for another 24h, and then concentrated under reduced pressure. The resulting residue was dissolved in MC and washed with water. The organic layer was concentrated and dissolved in 80ml THF and 80ml water, to which was added 8.4g of BoC2O dissolved in 50ml THF. The reaction mixture was stirred at RT for 16h, which was followed by removal of THF in vacuo and extraction with EA. The organic layer was washed in series with 0.5M aq citric acid, water, and brine. The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (hexane -> 1:4 EA/hexane) to obtain 2.45g of compd 9 as a pale yellow oil. 1H NMR (400MHz; CDCI3) delta 5.08 (br s, 0.5H), 4.93 (br s, 0.5H), 3.61-3.46 (m, 12H), 3.31 (m, 2H), 2.48 (m, 2H), 1.99 (t, IH), 1.48 (s, 9H), 1.46 (s, 9H).

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; CTI BIO; WO2009/113828; (2009); A2;,
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

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

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

Application of 143557-91-9, A common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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.

To a solution of tert-butyl (3-endo)-3-hyd roxy-8-azabicyclo[3.2.1 ]octane-8-carboxylate (3g, 13.20 mmol, combi-blocks) in THF (30 mL) was added portion wise potassium tertbutoxide (1.6 g, 14.5 mmol). The reaction was then refluxed for lh. The reaction was removed from the oil bath and 1-bromo-2,4-difluoro-benzene (1.6 mL, 14.52 mmol, Matrix) was added. The reaction was again refluxed for 1 .5h and cooled to RT. Ethyl acetate was added. The layers were separated and the organic layer was washed withwater, brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude was purified by flash chromatography using 5% ethyl acetate in cyclohexane to give a colourless oil that crystallised upon standing (4.1 g, 79%). 1H NMR (400 MHz, DMSOd 6): 67.63-7.59 (m, 1H), 6.98 (dd, J1= 11.40, J2= 2.76 Hz, 1H), 6.76-6.71 (m, 1H), 4.81 (t, J= 4.40 Hz, 1H), 4.06 (s, 2H), 2.15-2.05 (m, 4H), 1.87-1.84 (m, 4H), 1.41 (s, 9H).LCMS: (Method A) 344.0 (M-?Bu-f-H), Rt. 6.2 mm, 84.9% (Max).

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; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; MURUGESAN, Kathiravan; BANERJEE, Joydeep; WO2014/198808; (2014); A1;,
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;,
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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

6-Oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid methyl ester described in Preparation Example T-8 (9mg, 43mumol), N-phenyltrifluoromethanesulfonimide (23mg, 65mumol) and dimethyl-pyridin-4-yl-amine (catalytic amount) were dissolved in dichloromethane (0.5mL), and the solution was stirred for 18.5 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane : ethyl acetate = 3 : 1), and the title compound (10mg, 29mumol, 68%) was obtained as a white solid. 1H-NMR Spectrum (CDCl3) delta(ppm) : 4.03 (3H, s), 7.43 (1H, d, J=5.9Hz), 7.73 (1H, d, J=5.9Hz), 8.87 (1H, s).

According to the analysis of related databases, 456-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 26638-53-9, A common heterocyclic compound, 26638-53-9, name is 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, molecular formula is C14H10ClNO3S, 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.

N-bromosuccinimide (187 mg, 1.05 mmol) was added portionwise to a solution of ketone 3f (308 mg, 1.0 mmol) and FeCla (324 mg, 2.0 mmol) in CH2CI2 (10 mL) and CH3CN (5 mL) , and the reaction mixture was stirred at room temperature for 3 h. Additional W-bromosuccinimide (187 mg, 1.05 mmol) was then added and the reaction mixture was stirred at room temperature for a further 14 h. The reaction mixture was washed with water and brine and dried over NaSCli. The crude product was purified by column chromatography ( CH2CI2 : hexane – 2:1) followed by crystallization from MeOH. The product 3k was obtained as a white solid (290 mg, 75 percent) . XH NMR (400 MHz, Acetone-dg) 3 8.31 (d, J = 2.5 Hz, 1H) , 8.00 – 7.96 (m, 1H) , 7.95 – 7.89 (m, 3H) , 7.58 (d, J = 8.7 Hz, 1H) , 3.44 (s, 3H) ; 13C NMR (101 MHz, Acetone-dg) delta 189.6, 142.0, 139.1, 139.0, 138.4, 135.3, 134.7, 134.3, 132.8, 127.9, 125.8, 119.4, 39.3; LR-MS calcci. for C ,HioBrClN03S [M+H]+ 387.92, found 388.63.

The synthetic route of 26638-53-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; KRUEGEL, Andrew C.; HENKE, Adam; GASSAWAY, Madalee M.; RIVERS, Marie-laure; JAVITCH, Jonathan A.; SAMES, Dalibor; WO2015/138791; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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