Category: amides-buliding-blocks

Some common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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. 631-58-3

Reference Example H 11 2-ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazole A solution of 2-bromo-2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone hydrobromide (11 g, 29 mmol) and thiopropionamide (2.7 g, 30 mmol) in N,N-dimethylformamide (30 mL) was stirred for 14 hours at room temperature. Aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, then, the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane-ethyl acetate= 4:1) to obtain the title compound (3.3 g, yield 38%). oil 1H-NMR (CDCl3) delta: 1.64 (3H, t, J= 7.6 Hz), 2.34 (3H, s), 3.10 (2H, q, J= 7.6 Hz), 6.84-6.86 (1H, m), 7.05-7.09 (1H, m), 7.13-7.25 (3H, m), 7.37 (1H, s), 8.10 (1H, d, J= 5.6 Hz).

The chemical industry reduces the impact on the environment during synthesis Propanethioamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1402900; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

121492-06-6, 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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows.

Step 3 [0211] To a stirred solution of N-Boc-N-methyl ethylenediamine (1.39 g, 8.0 mmol) and DIEA (1.05 g, 8.1 mmol) in dry DCM (50 mL) at 0C was added a solution ofp- nitrobenzylchloroformate (1.75 g, 8.1 mmol) in dry DCM (10 mL) dropwise over 5- 10 minutes. The reaction mixture was stirred at this temperature for 30 minutes and then allowed to warm to room temperature, and stirred overnight (monitored by TLC). The reaction mixture was then washed with 1M aq. NaHC03 solution, water, and brine. The organic layer was dried over Na2S04, concentrated , and the remaining residue was purified by flash chromatography to give the desired N-Boc-N’-PNB protected intermediate in 73% yield.

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; FOB SYNTHESIS; WO2005/123066; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 42137-88-2

Example VII A solution of 29.6 parts of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide and 14.9 parts of 4-fluoro-2-methylbenzeneacetonitrile in 90 parts of methylbenzene is added dropwise to a solution of 5.6 parts of lithium amide in 270 parts of methylbenzene at about 90 C. Upon completion, the whole is heated to reflux and stirred overnight at reflux temperature. The reaction mixture is cooled, poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 27 parts (72.6%) of 4-(4-fluoro-2-methylphenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile.

The synthetic route of 42137-88-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4369184; (1983); A;,
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. 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., 90-16-4

0.294 g (2.0 mmol) of benzo[d][1,2,3]triazin-4(3H)-one,0.418 g (2.0 mmol) of 5-(2-chloroethyl)-3-phenyl-1,2,4-oxadiazole,0.276 g (2.0 mmol) of potassium carbonate was added to 20 ml of acetone, and the temperature was raised to reflux.TLC tracks the progress of the reaction. After the reaction is completed, the solvent is distilled off under reduced pressure.50 ml of saturated sodium chloride was added to the residue, and extracted with dichloromethane (50 ml ¡Á 2).The organic phase is dried over anhydrous sodium sulfate, concentrated and purified by column chromatography.A white solid of 0.49 g was obtained in a yield of 77%.

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; East China University of Science and Technology; Xu Xiaoyong; Li Zhong; Chen Xiulei; Li Wei; Jia Haowu; Cao Xiaofeng; Shao Xusheng; Xu Zhiping; (70 pag.)CN108276352; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 239074-29-4

A solution of tert-butyl [trans-4-(hydroxymethyl)cyclohexyl]carbamate (from Aldrich, 0.61 g, 2.7 mmol) in methylene chloride (10 mL) at 0 C. was added Dess-Martin periodinane (1.35 g, 3.19 mmol). The resulting mixture was stirred at room temperature overnight. The reaction was quenched with aq. 1 N NaOH solution, extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (0.3 g, 50%). LCMS calculated for C12H21NO3Na (M+Na)+: m/z=250.2. Found: 250.1.

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhu, Wenyu; Mei, Song; Glenn, Joseph; US2014/121198; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

90-16-4, A common compound: 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A stirring suspension of 1,2,3-benzotriazin-4-one (6 mmol), 1,2-dibromoethane (18 mmol), potassium carbonate (12 mmol), and acetone (50 ml) was refluxed for 5-8 h and then cooled to room temperature. The reaction mixture was evaporated under reduced pressure, and water (100 mL) was added to the residue, which was extracted with CH2Cl2 (50 mL ¡Á 2). The organic layer was dried over anhydrous Na2SO4, concentrated, and purified with flash chromatography on silica gel, eluting with petroleum ether (60-90C)/EtOAc to afford compound 5 in yield of 62%.

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, Benzo[d][1,2,3]triazin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Xiulei; Jia, Haowu; Li, Zhong; Xu, Xiaoyong; Chinese Chemical Letters; vol. 30; 6; (2019); p. 1207 – 1213;,
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. 811442-84-9, name is tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate, A new synthetic method of this compound is introduced below., 811442-84-9

TSTU (70 mumol), DIEA (80 mumol) and Boc-NH-PEG4-NH2 (68 mumol) are added to BDP acid 12 (68 mumol) in 1 mL DMF at 0 C. After 10 min, the ice bath is removed and stirring is continued for 2 h at room temperature (RT). The reaction mixture is poured over 3 mL ice cold water and purified by preparative HPLC. After concentration and lyophilization, Boc amine monomer 13 is obtained which is further treated with 1 mL 95% trifluoroacetic acid (TFA), and the solution is stirred at RT for 2.5 h. The excess TFA is removed by N2 stream. After lyophilization, the BDP acid conjugated terminal amine monomer 14 (87%) is obtained without further purification.

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; Bhushan, Kumar Ranjan; Misra, Preeti; US2014/58071; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 118753-70-1, name is tert-Butyl bis(2-chloroethyl)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 118753-70-1, 118753-70-1

To a stirred solution of 2-(4-fluorophenyl)acetonitrile (3.2 g, 23.7 mmol) and ie/ -butyl bis(2-chloroethyl)carbamate (DM, 6.69 g, 23.7 mmol) in DMF (40 mL), NaH (60percent, 2.8 g, 71.1 mmol) was added and the reaction mixture was stirred at 60C for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched using water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 10percent EtOAc/hexane to afford compound DN (4.2 g, 58percent) as a thick oil.

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 bis(2-chloroethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7462-74-0, 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. 7462-74-0, name is 2-Bromo-2-methylpropanamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 5 (R)-2-(3-N,N-Dibenzylamino-3,4-dihydro-2H-1-benzopyran-5-yloxy)-2-methylpropanamide (R)-3-N,N-Dibenzylamino-5-hydroxy-3,4-dihydro-2H-1-benzopyran (35.4 g, 100 mmol) was dissolved in anhydrous 1,4-dioxane (350 mL) under nitrogen. A dispersion of sodium hydride (60-65% in oil, 5.33 g, 130 mmol) was added in portions. The mixture was stirred for 2 h at room temperature. 2-Bromo-2-methylpropanamide (17.9 g, 110 mmol; described in Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc. Perkin Trans. 1 1990, 767-771) was added to the dark greenish solution and was heated at reflux with stirring for 3 h. After cooling, a small amount of water was added, the solution was decanted, and the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (350 mL) and a saturated NaHCO3 solution (50 mL). The organic layer was dried (MgSO4), and the solvent was removed in vacuo to give a brownish residue which was chromatographed on a short column of silica gel (eluent: hexane/ethyl acetate; 55:45) affording 27.6 g (64% yield) of the title compound as a white solid: mp 132-134 C.; [alpha]22D-92 (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 430 (6, M+).

The synthetic route of 7462-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astrazeneca AB; US6479497; (2002); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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. 16066-84-5

To a stirred suspension of 6-iodo-3 -((8-methoxy-2-(6-methoxypyridin-3 -yl)-2,3dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-3H-imidazo[4, 5-b]pyridine (0.20 g, 0.38 mmol, Example 1-52-9) in 1,4-dioxane (5 mL) was added tert-butyl-N-methylcarbamate (0.10 g,0.75 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.018 g, 0.019 mmol), 4,5- bi s(diphenylphosphino)-9, 9-dimethylxanthene (0.044 g, 0.075 mmol) and cesium carbonate (0.18 g, 0.57 mmol). The mixture was degassed under vacuum/backfilled with nitrogen (x3). The mixture was then heated to 115 C. After 18 h, the mixture was allowed to cool to room temperature and was concentrated. Chromatographic purification of the crude product(Biotage, 12 g silica gel column, ethyl acetate/heptane elute) provided semi-pure material. This material was dissolved in dichloromethane (10 mL) and was treated with trifluoroacetic acid (6 mL). The mixture was allowed to stir at room temperature. After 15 mm, the mixture was concentrated. The residue was dissolved in methanol and was neutralized by the addition of solid potassium carbonate. The mixture was filtered and concentrated.Chromatographic purification of the crude product (Biotage, 12 g silica gel column, 0-8% methanol/ethyl acetate elute) provided 0.020 g (12%) of 3-((8-methoxy-2-(6- methoxypyridin-3 -yl)-2,3 -dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-N-methyl-3H- imidazo[4,5-b]pyridin-6-amine as a light yellow solid: ?H NIVIR (400 IVIFIz, CDC13) 8.22 – 8.18 (m, 1H), 7.95 (d, J= 2.5 Hz, 1H), 7.92 (s, 1H), 7.61 (dd, J= 8.6, 2.5 Hz, 1H), 7.28 (d, J= 2.5 Hz, 1H), 6.77 (dd, J= 8.5, 0.7 Hz, 1H), 6.54 – 6.48 (m, 2H), 5.30 (s, 2H), 5.09 (dd, J8.4, 2.5 Hz, 1H), 4.29 (dd, J= 11.6, 2.5 Hz, 1H), 4.06 (dd, J= 11.6, 8.4 Hz, 1H), 3.93 (s, 3H), 3.79 (s, 3H), 2.91 (s, 3H) ppm; (M+1) = 434.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16066-84-5.

Reference:
Patent; GENZYME CORPORATION; KANE, John, L., Jr.; BARBERIS, Claude; CZEKAJ, Mark; ERDMAN, Paul; GIESE, Barret; KOTHE, Michael; LE, Tieu-binh; LIU, Jinyu; MA, Liang; METZ, Markus; PATEL, Vinod; SCHOLTE, Andrew; SHUM, Patrick; WEI, Limli; (408 pag.)WO2017/15267; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics