Month: September 2021

Related Products of 125414-41-7, A common heterocyclic compound, 125414-41-7, name is tert-Butyl (1,3-dihydroxypropan-2-yl)carbamate, molecular formula is C8H17NO4, 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.

Preparation K Acetic acid 3-acetoxy-2-tert-butoxycarbonylamino-propyl ester (2-Hydroxy-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester (5.0 g, 26.1 mmol) was dissolved in pyridine (50 ml) and acetic anhydride (50 ml) was added. The solution was stirred at ambient temperature for 24 h when TLC showed no starting material remained. The solvent was evaporated and the residue dissolved in ethyl acetate (120 ml) and washed with dilute hydrochloric acid (3*50 ml), sodium bicarbonate solution (50 ml), brine, dried over magnesium sulphate, filtered and evaporated to give a colourless oil (7.2 g, 99% yield). The structure was confirmed by 1H NMR (300 MHz, CDCl3): 1.42 (s, 9H), 2.05 (s, 6H), 4.00-4.20 (m, 4H), 4.76-4.88 (m, 1H).

The synthetic route of 125414-41-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Morrison-Iverson, Veronique; Wynn, Duncan George; US2010/233097; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 579474-47-8, 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. 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-(8-Fluoro-2-oxo-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)picolinonitrile (1b). tert-Butyl (2-amino-4-fluorophenyl)carbamate (0.226g, 1mmol) and tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate (0.320g, 1.3mmol) were dissolved in toluene (5mL) and heated at reflux for 1h. The reaction mixture was cooled and the excess solvent was removed under reduced pressure. The crude intermediate was taken up in CH2Cl2 and TFA (1.14g, 10mmol) was added dropwise to it at 0C. The resulting reaction mixture was stirred at rt for 7h. The crude mixture was washed with sodium bicarbonate solution and the aqueous layer extracted with CH2Cl2. The combined organic layers were washed with water, then brine, and dried over Na2SO4. Evaporation of the solvent followed by column chromatography using hexanes:ethyl acetate (60:40) yielded the title compound.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 2-amino-4-fluorophenylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Dhanya, Raveendra Panickar; Herath, Ananda; Sheffler, Douglas J.; Cosford, Nicholas D.P.; Tetrahedron; vol. 74; 25; (2018); p. 3165 – 3170;,
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 24243-71-8 as follows. COA of Formula: C3H9NO2S

In DMSO were dissolved 2,3-dichloroquinoxaline (5.00 g, 25.1 mmol) and propane-1-sulfonamide (3.09 g, 25.1mmol). Potassium carbonate (3.47 g, 25.1 mmol) was added and the mixture was stirred at 150C for 1 hour. A 1%aqueous acetic acid solution was added to the mixture and the mixture was stirred at room temperature for 3 hours. Theprecipitated solid was separated by filtration and the obtained solid was washed with water. The separated solid wasthen purified by slurrying in diisopropyl ether to give compound AA (6.01 g, 84% yield).

According to the analysis of related databases, 24243-71-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; KANAI, Toshimi; UCHIDA, Kenji; HONMA, Masakazu; FUKUDA, Yuichi; (51 pag.)EP2781517; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, 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 207405-68-3, name: tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

Into a 250-mL 3-necked round-bottom flask was placed tert-butyl (1R,3r,5S)-3- amino-8-azabicyclo[3.2.1]octane-8-carboxylate (5 g, 22.09 mmol, 1.00 equiv), water (100 mL), and NaHCO3(4.83 g, 149.50 mmol, 2.60 equiv). The solution was cooled to 0oC and 2,2,2-trichloroethyl chloroformate (5.63 g, 26.57 mmol, 1.20 equiv) added dropwise over 10 mins. The resulting solution was stirred at room temperature overnight. The reaction mixture was extracted with 3×100 mL of dichloromethane and the organic layers combined. The combined extracts were washed with 3×100 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The resulting residue was washed with 3×100 mL of hexane. This resulted in 8.32 g (94%) of tert-butyl (1R,3r,5S)-3-[[(2,2,2-trichloroethoxy)carbonyl]amino]-8-azabicyclo[3.2.1]octane-8- carboxylate as a white solid

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; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 83922-54-7, These common heterocyclic compound, 83922-54-7, name is 4-(Methylsulfonamido)benzaldehyde, 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 [INTERMEDIATE] 11 (0.0088 mol) [AND N- (4-FONNYLPHENYL)-] [METHANESULFONAMIDE] (0.012 mol) in [ETOH] (20ml) was stirred and refluxed for 3 hours, then brought to room temperature. The precipitate was filtered off and dried. Yielding: 2.34g of intermediate 30 (75%).

The synthetic route of 83922-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/7498; (2004); A2;,
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 2895-21-8 as follows. HPLC of Formula: C5H10ClNO

General procedure: The corresponding CH-acid 1a-f (25 mmol) was dissolved in a solution of potassium hydroxide (1.4 g, 25 mmol) in ethanol (50 ml) at 10 C. In several cases after addition of 1 a precipitate was formed, which did not have an effect on the reaction conditions or the final product. After stirring for 1 min carbon disulfide (1.5 ml, 25 mmol) was added to the resulting solution, and the reaction mixture was stirred for 20 min. Water (10-15 ml) was added to the mixture to dissolve the resulting precipitate. Subsequently, ester 4 (3.4 ml, 25 mmol) in ethanol (20 ml) was added to the reaction mixture dropwise for 1 h, which was quenched with potassium hydroxide solution (2.8 g, 50 mmol) in ethanol (100 ml), after stirring for 10 min. The resulting reaction mixture was refluxed for 2.5 h. After cooling to room temperature, the solution was quenched with concentrated HBr (2.8 ml, 25 mmol), stirred for 30 min, and divided into five equal portions. Each portion was then reacted with the corresponding alkylhalide 8a-t (5 mmol) under refluxing conditions for 1 min. After cooling the reaction to room temperature, the resulting precipitate was filtered off and rinsed on the filter to give pure thieno[3,2-b]pyridines 9a-af in 58-88% yield.

According to the analysis of related databases, 2895-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zubarev, Andrey A.; Shestopalov, Anatoliy M.; Larionova, Natalia A.; Rodinovskaya, Lyudmila A.; Shestopalov, Alexander A.; Tetrahedron; vol. 69; 46; (2013); p. 9648 – 9655;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 304460-78-4,Some common heterocyclic compound, 304460-78-4, name is N-[1-(Hydroxymethyl)propyl]-4-methylbenzenesulfonamide, molecular formula is C11H17NO3S, 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 mixture of alcohol 6 (1 mmol), N,Se acetal 5 (1.4 mmol) and activated 3-A molecular sieves (0.40 g) in dry dichloromethane (16 mL) was stirred for 0.5 h under argon atmosphere at room temperature. Solid N-iodosuccinimide (1.4 mmol) was added and then the mixture cooled to -15 C. After the addition of TMSOTf (12 muL, 0.07 mmol) the reaction mixture was stirred and monitored by TLC. Reaction times ranged from 1 to 2 h. The brown colored reaction mixture was then filtered through a celite path and the filtrate washed with 20 mL of 10% aqueous sodium thiosulfate pentahydrate solution. The aqueous phase was extracted with 10 mL of dichloromethane and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate, and then evaporated under vacuum. Purification by silica gel column chromatography afforded the phthalimidomethyl-ether derivative 7.

The synthetic route of 304460-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Temperini, Andrea; Minuti, Lucio; Tetrahedron Letters; vol. 53; 22; (2012); p. 2709 – 2711;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18437-67-7, name is tert-Butyl m-tolylcarbamate, 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 18437-67-7, category: amides-buliding-blocks

General procedure: To a mixture of tert-butyloxycarbamates (8.0 mmol), K3PO4 (16 mmol), CuSO4*5H2O (0.8 mmol), and 1,10-phenanthroline (1.6 mmol) in a reaction vial was added a solution of bromoalkyne (8.8 mmol) in toluene (15 mL).The reaction mixture was capped and heatedin an oil bath at 85 C for 18 h while being monitored with TLC analysis. Upon completion, the reaction mixture was cooled to room temperature and diluted with EtOAc and filtered through Celite, and the filtrate was concentrated in vacuum. The crude products were purified by silica gel flash chromatography on a silica gel column with petroleum ether (PE) and ethylacetate (EA) as eluent to afford directing products.

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:
Article; Huang, Hai; Tang, Luning; Xi, Yang; He, Guangke; Zhu, Hongjun; Tetrahedron Letters; vol. 57; 17; (2016); p. 1873 – 1876;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 112257-19-9, The chemical industry reduces the impact on the environment during synthesis 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, I believe this compound will play a more active role in future production and life.

A mixture of 3-iodo- l-(oxan-2-yl)-lH-pyrazole-4-carbaldehyde (21.5 g, 70.24 mmol, 1.00 equiv), iert-butyl N-methyl-N-(2-(methylamino)ethyl)carbamate (20 g, 106.23 mmol, 1.51 equiv) and NaBH(OAc)3 (29.8 g, 137.98 mmol, 1.96 equiv) in dichloroethane (300 mL) was stirred for 1 h at room temperature. The reaction was diluted with 300 mL of dichloromethane and then washed with 3×300 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-7percent methanol in dichloromethane to give 31 g (92percent) of tert- butyl (2-(((3-iodo- l-(tetrahydro-2H-pyran-2-yl)- lH-pyrazol-4- yl)methyl)(methyl)amino)ethyl)(methyl)carbamate as a yellow oil. 1H-NMR (300 MHz, CDC13): delta 7.62 (s, 1H), 5.34-5.30 (m, 1H), 4.06-4.02 (m, 1H), 3.68-3.62 (m, 1H), 3.42-3.38 (m, 4H), 2.85 (s, 4H), 2.62-2.53 (m, 2H), 2.47-2.46 (m, 2H), 2.13-1.97 (m, 3H), 1.74- 1.69 (m, 3H), 1.46 (s, 9H) ppm. LCMS (method A, ESI): RT = 1.17 min, m/z = 479.0 [M+H]+.

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, tert-Butyl methyl(2-(methylamino)ethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MITCHELL, Lorna, Helen; CAMPBELL, John, Emmerson; REITER, Lawrence, Alan; SWINGER, Kerren, Kalai; (387 pag.)WO2016/44626; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 16313-66-9, A common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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 34. Preparation of 2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-6-((4-methyIpiperazin-1-yl)methyl)quinazolin-4(3H)-one [0274] To a solution of 4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5- dimethylbenzaldehyde (7.5 g, 24.4 mmol) in DMA (50 mL) was added 2-amino-5-bromobenzamide (5.2 g, 24.4 mmol), NaHSO3 (3.9 g, 36.5 mmol) and p-TsOH (0.46 g, 2.4 mmol), and the reaction was heated at 1600C. After 1 hour, the resulting mixture was cooled to room temperature, diluted with water, and filtered to afford 6-bromo-2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (6.7 g, 55%) as a white solid (6.7 g, 55%).[0275] A mixture of 6-bromo-2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (5.0 g, 9.9 mmol), vinyltributyltin (4.3 mL, 14.9 mmol) and PdCI2(PPh3)2 (0.70 g, 1.0 mmol) in CH3CN (150 mL) was stirred at reflux overnight. Then, additional PdCI2(PPh3)2 (0.10 g, 0.14 mmol) and vinyltributyltin (2.0 mL, 6.8 mmol) were added and the reaction continued to reflux overnight. The resulting mixture was cooled to room temperature, filtered through celite, and the filtrate concentrated. The residue was purified by flash chromatography (silica, eluting with 98:2 CH2CI2/Me0H) to afford 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-6-vinylquinazolin-4(3H)-one (2.0 g, 45%).[0276] To a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-6-vinylquinazolin-4(3H)-one (0.63 g, 1.4 mmol) in THF (50 mL) and H2O (5 mL) was added NaIO4 (0.90 g, 4.2 mmol) and OsO4 (0.11 mL, 0.014 mmol), and the reaction was stirred overnight at room temperature. Then, the mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, eluting with 98:2 to 95:5 CH2CI2/MeOH) to afford 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-4-oxo-3,4-dihydroquinazoline-6-carbaldehyde (0.52 g, 82%). [0277] A solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-4-oxo-3,4-dihydroquinazoline-6-carbaldehyde (0.11 g, 0.24 mmol) in DCE/CH2CI2 (1 :1 , 15 ml_) was treated with 1-methylpiperazine (0.05 ml_, 0.48 mmol) and NaBH(OAc)3 (0.103 g, 0.48 mmol) and the reaction mixture was stirred at room temperature overnight. Then, the mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, eluting with 60% of 92:7:1 CHCI3/MeOH/concentrated NH4OH in CH2CI2) to afford 2-(4- (2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-6-((4-methylpiperazin-1-yl)methyl)quinazolin-4(3H)-one (0.14 g, 98%).[0278] A solution of 2-(4-(2-(terf-butyldimethylsilyloxy)ethoxy)-3,5- dimethylphenyl)-6-((4-methylpiperazin-1-yl)methyl)quinazolin-4(3H)-one (0.087 g, 0.16 mmol) in a 1 M TBAF/THF solution (1.3 mL, 1.3 mmol) was stirred for 2 hours at room temperature. Then, the resulting mixture was concentrated in vacuo and purified by flash chromatography (silica gel, eluting with 70% of 92:7:1 CHCI3/MeOH/concentrated NH4OH in CH2CI2) to afford the title compound (0.070 g, 100%): 1H NMR (300 MHz, DMSO-d6): delta 12.31 (s, 1H), 8.02 (s, 1 H), 7.89 (S, 2H), 7.56-7.79 (m, 2H), 4.92 (t, J = 5.3 Hz, 1 H), 3.77-3.93 (m, 2H), 3.64- 3.75 (m, 2H), 3.58 (s, 2H)1 2.21-2.45 (m, 14H), 2.15 (s, 3H). APCI MS m/z 423

The synthetic route of 16313-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics