Category: amides-buliding-blocks

Some common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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. Safety of tert-Butyl (2-hydroxyethyl)(methyl)carbamate

Route ASynthesis of compound 1: 7.5 ml (85 mmol) oxalyl chloride was dissolved in 200 ml DCM and cooled to T < -60 C and 12.1 ml (171 mmol) DMSO in 10 ml DCM was added dropwise (T < -60 C) and stirred an additional 10 min. 10.0 g (57 mmol) N-Boc-N-methylaminoethanol in 40 ml DCM were added dropwise (T < -60 C) and stirred an additional 10 min. 40 ml (285 mmol) Et3N was added dropwise followed by 50 ml DCM (T < -60 C) and stirred for 30 min. The reaction mixture was warmed to 0 C and washed with 3x100 ml water, 100 ml 0.5 M KHS04, 75 ml brine, dried with MgS04 and concentrated in vacuo. The product was purified by column chromatography (Si02, DCM/ethyl acetate, 1 :0 to 9: 1) to give 7.36 g (74%) of compound 1. 1H-NMR (300MHz, CDC13): delta = 1.42/1.46 (s, 9H, Boc), 2.93/2.96 (s, 3H, Me), 3.90/4.01 (s, 2H, CH2), 9.60 (s, 1H, CHO). Z/E isomers. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57561-39-4, its application will become more common. Reference:
Patent; SYNTARGA B.V.; BEUSKER, Patrick, Henry; COUMANS, Rudy, Gerardus, Elisabeth; ELGERSMA, Ronald, Christiaan; MENGE, Wiro, Michael, Petrus, Bernardus; JOOSTEN, Johannes, Albertus, Frederikus; SPIJKER, Henri, Johannes; DE GROOT, Franciscus, Marinus, Hendrikus; WO2011/133039; (2011); A2;,
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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. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromomethylbenzenesulfonamide

Example 7 4-(trityithiomethyi)benzenesulfonamide To a stirred solution of triphenylmethanethiol (0.276g, 2equiv) in N,N- dimethylformamide (3 mL) at 0¡ãC was added sodium hydride (60percent w/w dispersion in mineral oil, 0.04g, 2 equiv). When the effervescence had ceased, 4- (bromomethyi)benzenesuifonamide (0.125g, 1 equiv) was added in a single portion and the reaction was allowed to warm to room temperature. HPLC-MS at 20 minutes indicated that conversion was complete. The reaction was quenched with acetic acid (-0.2 mL), concentrated to dryness in vacuo and the subsequent residue partitioned between ethyl acetate and brine. The organic layer was separated, dried over MgS04, filtered, concentrated and purified by flash chromatography (0-50percent ethyl acetate in hexanes). Fractions containing the desired material were concentrated to dryness to furnish the desired compound as a colourless solid (0.200g). f H NMR (400MHz, DMSO-d6) delta (ppm) H), 7.36-7.44 (m, 12H), 7.67-7.73 (m, 2H)

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; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; WINTERS, Geoffrey C.; MANDEL, Alexander Laurence; RICH, James R.; HEDBERG, Bradley John; HSIEH, Tom Han Hsiao; BOURQUE, Elyse Marie Josee; BABCOOK, John; WO2014/144871; (2014); A1;,
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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. 70-55-3, name is 4-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Methylbenzenesulfonamide

Example 3 p-Aminosulfonyl-benzoic Acid To the solution of 17.1 g (0.1 mol) of p-toluenesulfonamide prepared in Example 1, 20 g (0.5 mol) of sodium hydroxide in 300 ml of water was added in portions 20 g (0.13 mol) of potassium permanganate. The temperature raised to 70 C. spontaneously, keep the reaction mixture in 90 C. for 2 h. The mixture was then cooled and filtered, and the filtrate was acidified with HCl. The resulting precipitate was filtered, and washed with water, dried in vacuo to give the title compound (18.1 g) as white powder, yield 90%, m.p. 291-292 C.

The synthetic route of 70-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guo, Zongru; Cheng, Guifang; Chu, Fengming; US2004/58977; (2004); A1;,
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Reference of 143557-91-9,Some 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, 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.

After dissolving (endo)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (CAS 143557-91-9) (2.00 g) and 1-(3-chloropropyl)-2-fluorobenzene (CAS 110406-96-7) (1.67 g) in N,N-dimethylformamide (10 ml), tetra-n-butylammonium iodide (325 mg) was added to the solution. Sodium hydride (60% in oil) (422 mg) was added and the mixture was stirred at room temperature for 17 hours and 30 minutes. Sodium hydride (60% in oil) (352 mg) was added to the reaction mixture, and stirring was continued for 2 hours at room temperature. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (1.20 g).1H-NMR (400 MHz, CDCl3); delta 1.46 (s, 9H), 1.81-1.95 (m, 8H), 2.06-2.11 (m, 2H), 2.71-2.75 (m, 2H), 3.37-3.38 (m, 2H), 3.54-3.56 (m, 1H), 4.10-4.18 (m, 2H), 6.98-7.07 (m, 2H), 7.14-7.21 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2009/270369; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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 1314538-55-0, Product Details of 1314538-55-0

84- iii (0.27 g, 0.45 mmol, 1 .0 equiv), potassium (((tert-butoxycarbonyl) amino) methyl) trifluoroborate (0.21 g, 0.89 mmol, 2.0 equiv) were added to toluene: water (5: 0.5) and the reaction mixture was degassed for 5 minutes. Pd (ll)OAc (0.005 g, 0.022 mmol, 0.05 equiv), RuPhos (0.02 g, 0.044 mmol, 0.1 equiv), K2CO3 (0.19 g, 1 .34 mmol, 3.0 equiv) were added and the reaction mixture was stirred at 80 C for 24 hours. The reaction mixture was quenched with cold water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by preparative HPLC purification to afford the desired product 85-i (0.038 g, 15 % yield). 1H NMR (400 MHz, MeOD) delta 7.27 (s, 1 H), 7.09 (s, 1 H), 6.43 (s, 1 H), 4.49 (s, 2H), 3.96 – 3.80 (m, 2H), 3.53 (dd, J = 18.0, 5.8 Hz, 5H), 2.47 (s, 3H), 2.23 (d, J = 7.5 Hz, 1 H), 2.18 (d, J = 7.7 Hz, 1 H), 1 .48 (d, J = 10.2 Hz, 18H), 1 .15 (d, J = 5.5 Hz, 1 H), 0.90 (d, J = 7.1 Hz, 1 H), 0.53 – 0.43 (m, 2H) LCMS (m/z): 581 .5 [M+H]

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; NOVARTIS AG; FIDALGO, Javier De Vicente; HE, Haiying; HU, Cheng; JIANG, Zhigan; LI, Xiaolin; LU, Peichao; MERGO, Wosenu; MUTNICK, Daniel; RECK, Folkert; RIVKIN, Alexey; SKEPPER, Colin Kevin; WANG, Xiaojing Michael; XIA, Jianhua; XU, Yongjin; (285 pag.)WO2016/20836; (2016); A1;,
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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. 6873-44-5, name is 4-Chloro-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6873-44-5

EXAMPLE IV N-Methyl 4-Chlorobenzimidoyl Chloride N-Methyl 4-chlorobenzamide (42.6 g, 251 mmole) and thionyl chloride (153.3 g, 1.28 mole) were reacted as in Example I to yield 39.3 g (83.4%) of the title compound, b.p. 125 C. (15 mm Hg).

The synthetic route of 6873-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McNeilab, Inc.; US4528382; (1985); A;,
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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. 156731-40-7, name is 1-(Boc-amino)-3-butene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(Boc-amino)-3-butene

Freshly distilled acrolein (2.5ml, 2.1g, 38mmol) and CSA (175mg, 0.752mmol) were added to an ice-cooled solution of N-Boc-butenylamine 25 (644mg, 3.76mmol) in CH2Cl2 (8ml). The resulting solution was stirred at 0C for 15min and at ambient temperature for 45min. The mixture was then washed with satd NaHCO3 solution (10ml) and the organic layer dried (MgSO4). After filtration, the solvent was removed and the residue purified by chromatography on SiO2 (hexane/MTBE 1:1, Rf=0.36) to yield title compound 26 (684mg, 3.01mmol, 80%) as a colorless oil. 1H NMR (500MHz, CDCl3): delta=1.40 (s, 9H), 2.18-2.27 (m, 2H), 2.62-2.70 (m, 2H), 3.17-3.26 (m, 2H), 3.42-3.51 (m, 2H), 4.95-5.06 (m, 2H), 5.66-5.78 (m, 1H), 9.75 (t, J=1.6Hz, 1H)ppm. 13C{1H} NMR (125MHz, CDCl3): delta=28.27 (3CH3), 32.68 (CH2), 33.28 (CH2), 41.24 (CH2), 43.27 (CH2), 43.68 (CH2), 47.02 (CH2), 47.52 (CH2), 79.68 (C), 116.68 (CH2), 135.18 (CH), 154.99 (C), 155.34 (C), 200.72 (CH), 201.03 (CH)ppm. IR (ATR): 3077 (w), 2976 (m), 2930 (w), 1688 (vs), 1478 (m), 1415 (s), 1366 (s), 1249 (m), 1167 (vs), 1064 (m), 913 (m), 773 (m)cm-1. HRMS (CI, isobutane): calcd 228.1600 (for C12H22NO3), found 228.1603 [M+H+]. C12H21NO3 227.30.

The synthetic route of 156731-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wuerdemann, Martina; Christoffers, Jens; Tetrahedron; vol. 70; 31; (2014); p. 4640 – 4644;,
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Electric Literature of 202207-79-2, 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. 202207-79-2, name is 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Chloro-5- { [2-oxo- 1 -( lH-pyrazolo[3 .4-&]pyridin-3-ylmethyl)-4-(trifluoromethyl)-l,2-dihydropyridin-3-yl)oxy}benzonitrile_(6.0 g, 13.46 mmol) was stirred in DMA (140 mL) until dissolved and then cooled over ice bath for 10 minutes. This solution was treated with diisopropylethylamme (4.70 mL, 26.9 mmol) and then 4-nitrophenyl chloroformate (3.26 g, 16.15 mmol) portionwise over 5 minutes. This mixture was allowed to warm to room temperature and then stirred for 30 minutes. Formation of the intermediate carbamate was monitored by queching a small aliquot of the reaction mixture with dimethylamine and monitoring by LC-MS. The reaction mixture was then recooled over an ice bath and the cooled mixture was treated with a solution of 2-[(/er/-butoxycarbonyl)amino]-N-methylethanaminium chloride (3.40 g, 16.15 mmol) and diisopropylethylamme (2.5 mL, 14.3 mmol) in DMA (35 mL). Upon completion of addition, the cooling bath was removed and the mixture stirred for 1 hour at room temperature. This mixture was partitioned between ethyl acetate (1000 mL and 500 mL) and water (500 mL). The combined extracts were further washed with water (3x 00 mL), dried over MgS04, filtered and the solvent removed by evaporation in vacuo. This residue was pre- absorbed onto silica gel (35 g) using ethyl acetate and purified by silica gel (330 g)chromatography eluting with 0-100% ethyl acetate in hexanes. The desired fractions were combined and then solvent was removed by evaporation in vacuo. The resulting residue was further purified by re-crystallizing from ethyl acetate (75 mL) to give the title compound as a white solid. lH NMR (CDCI3) delta-8.68 (d, 1H), 8.26 (d, 1H, J = 7 Hz), 7.72 (d, 1H), 7.39 (dd, 1H, J=1.5Hz), 7.30 (dd, 1H5 3=4.6 and 8Hz), 7.16 (dd, 1H, J=2Hz), 7.02 (dd, 1H, J=1.3 and 2.3 Hz), 6.46 (d, 1H, J=7 Hz), 5.18 (bs t, 1H), 5.50 (s, 2H), 3.7 (br, 2H), 3.52 (br, 2H), 3.17 (s, 3H) and 1.44 (s, 9H) ppm. LRMS (M+l): 646.1

The synthetic route of 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; JOLLY, Samson, M.; ANTHONY, Neville; GOMEZ, Robert; DUBOST, David, C.; WOODWARD, Rick, G.; WO2011/126969; (2011); A1;,
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78191-00-1, name is N-Methoxy-N-methylacetamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of N-Methoxy-N-methylacetamide

Toluene-4-sulfonic acid 6-bromo-pyridin-3-yl ester (XVI) (980 mg, 2.99 mmol) was dissolved in tetrahydrofuran (THF) (3 mL) and the resulting solution was cooled to -78 C. 2.0 M lithium diisopropylamide (LDA) (2.24 mL, 4.48 mmol) dissolved in tetrahydrofuran was slowly added dropwise to the solution and the solution was stirred at -78 C for 3 hrs. And then, N-methoxy-N-methyl acetamide (609.77 muL, 5.97 mmol) was slowly added dropwise to the solution and the solution was stirred for 2 hrs. Saturated sodium hydrogen carbonate (NaHCO3) solution was added dropwise to the solution and the solution was diluted with ethylacetate (EA). Then, the organic solvent was dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated under reduced pressure to concentrate. The resulting residue was isolated and purified by silica gel column chromatography (n-Hex/EA = 4/1) to give the title compound (570 mg, 52 %). 1H NMR (400 MHz, CDCl3) delta 7.97 (s, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.65 (s, 1H), 7.37 (d, J = 8.0 Hz, 2H), 2.58 (s, 3H), 2.49 (s, 3H).

The synthetic route of 78191-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
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Application of 563-83-7, 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 563-83-7 as follows.

A. 2-Methylpropanethioamide Phosphorus pentasulfide (3.25 g, 14.6 mmol) was added to a solution of 2-methylpropanamide (5.00 g, 57.4 mmol) in diethyl ether/benzene (2:1; 150 mL). The mixture was stirred for 2.5 h at room temperature to give a tacky yellow solid and a supernatant layer. The supernatant was filtered through Celite and the tacky yellow solid was extracted with diethyl ether (3*25 mL) and the extracts were filtered through Celite. The combined organic layers were evaporated to give 2-methylpropanethioamide (4.6 g, 78% yield) as a yellow oil that solidified on standing.

According to the analysis of related databases, 563-83-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fotouhi, Nader; Gillespie, Paul; Guthrie, Robert William; Pietranico-Cole, Sherrie Lynn; Yun, Weiya; US2002/161237; (2002); A1;,
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