Amides-buliding-blocks

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;,
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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,
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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;,
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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,
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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;,
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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,
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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

Related Products of 49834-22-2,Some common heterocyclic compound, 49834-22-2, name is 3-Bromo-N-methylbenzamide, molecular formula is C8H8BrNO, 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.

[0121] In a dry 50 mL round bottom flask, 2-chloro-5-methyl-pyrirnidin-4-ylamine (0.3 g, 2.09 mmol, 1 equiv), 3-bromo-N-methyl-benzamide (0.489g, 2.29 mmol, 1.1 equiv), cesium carbonate (2.04.g, 6.27 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.242 g, 0.418 mmol, 0.2 equiv) and tris(dibenzylideneacetone) dipalladium (0.191 g, 0.209 mmol, 0.1 equiv) were combined. Reactants were diluted with dioxane (20 mL), flushed with argon and outfitted with reflux condenser. Reaction was heated to reflux for 16 hours. Reaction was then transferred into centrifuge tube, spun down, decanted and evaporated. Resulting yellow solids were diluted with DCM and adsorbed onto silica gel. Chromatography (gradient of 50% ethyl acetate in hexanes up to 100% ethyl acetate) afforded the title intermediate 17 as a pale yellow powder (0.25 g, 43% yield). MS (ESI+): 277.01 (M+H), r.t. = 1.92 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-N-methylbenzamide, its application will become more common.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 60144-53-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(4-Fluoro-phenyl)-carbamic acid terf-butyl ester (2.1 1 g, 10.0 mmol, ABCR, Karlsruhe, Germany) was added to a round bottom and purged with nitrogen. Anhydrous tetrhydrofuran (200 mL) was added to dissolve the solids and the flask placed in a dry ice / acetone bath (internal temperature -74 C uncorrected). terf-Butyl lithium (1 .7 M in pentane, 14.2 mL, 24.0 mmol) was added over 5 min causing a yellow color to develop. After the addition was complete the reaction was stirred in a -20 C bath for 1 h. At this point, 3-ethoxymethacrolein (1.43 mL, 12.0 mmol) was added dropwise over 5 min, keeping the temperature below -19 C. The reaction was stirred at -20 C for 2 h before slowly adding trifluoroacetic acid (14 mL) over 5 min. The red solution was stirred at room temperature for 16 h before bring to pH 12 with 1 N NaOH. This was extracted twice with ethyl acetate and the combined organics dried over MgS04. Purification by silica gel flash chromatography (ethyle acetate / heptanes) gave impure desired material. This was extracted into three portions of 1 N HCI, the combined aqueous layers were brought to pH 12 with 6 N NaOH, and then extracted into two portions of ethyl acetate. The combined organics were dried over MgS04 and concentrated in vacuo to give 6-fluoro-3-methyl-quinoline (48.0 mg) as an orange oil. 1 H NMR (400 MHz, CDCI3) delta 8.74 (s, 1 H) 8.07 (dd, J=9.1 , 5.4 Hz, 1 H) 7.88 (s, 1 H) 7.33 – 7.46 (m, 2 H) 2.53 (s, 3 H); MS (M+1 ): 162.1 .

The synthetic route of tert-Butyl (4-fluorophenyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; DIDIUK, Mary; FILIPSKI, Kevin J.; GUZMAN-PEREZ, Angel; LEE, Esther C.; PFEFFERKORN, Jeffrey A.; STEVENS, Benjamin; TU, Meihua; WO2013/14569; (2013); A1;,
Amide – Wikipedia,
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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. 102562-86-7, name is 3-(Aminomethyl)benzamide, A new synthetic method of this compound is introduced below., Recommanded Product: 3-(Aminomethyl)benzamide

To a solution of Intermediate 1h (50 mg, 0.152 mmol) and 3-aminomethyl-benzamide (60 mg, 0.228 mmol) in 2 mL DMF, were added iPr2Net (106 muL, 0.608 mmol), HOAT (41.4 mg, 0.304 mmol) and EDCI (35 mg, 0.182 mmol). The mixture was stirred at rt for 14 h, then was diluted with EtOAc. The organic phase was washed with H2O, 1N HCl, H2O, 0.1 N, NaOH, and brine, dried (Na2SO4), and concentrated. The crude product was recrystallized from methanol to afford 7.2 mg (10%) of Example 24. MS (HR-ESI) calculated for C24H24N5O5 (M+H+), found 462.1787; MS (ESI) 462.3 (M+H+), 484.3 (M+Na+); 1H NMR (300 MHz, CD3OD) delta. 8.51 (br. S, 1H), 7.84 (s, 1H), 7.78 (d, J=7.7, 1H), 7.53-7.31 (m, 7H), 5.20 (s, 2H), 5.13 (dd, J=3.0, 1.0, 1H), 4.61-4.37 (m, 2H), 3.25-3.16 (m, 1H), 3.12-3.03 (m, 1H), 2.66-2.55 (m, 1H), 2.32-2.24 (m, 1H).

The synthetic route of 102562-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glunz, Peter W.; US2004/6065; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics