Amides-buliding-blocks

A common heterocyclic compound, 6274-22-2, name is 4-Amino-N-methylbenzamide, molecular formula is C8H10N2O, 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. 6274-22-2.

Step 1To a solution of 2, 4-dichloropyridine (0.500 g, 3.39 mmoL) and 4-amino-N- methylbenzamide (0.510 g, 3.39 mmoL) in dimethylacetamide (1 mL) was added cesium carbonate (1.6 g, 5.08 mmoL) and the reaction mixture was degassed for 15 min. Pd2(dba)3 (0.154 g, 0.169 mmol) and BINAP (105 mg, 0.169 mmol) were added and the reaction mixture was irradiated in the microwave at 120 C for 1 h. Then reaction was quenched with water and extracted with EtOAc (2 x 50 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-((4-chloropyridin-2-yl)amino)-N-methylbenzamide (0.300 g, 38%) as a solid. Observed mass (M+l): 262.1

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

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin, F.; DU, Bingfan; NGUYEN, Hanh, Nho; ZHENG, Xiao, Mei; WO2011/103196; (2011); 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. 49805-30-3, name is 2-Azabicyclo[2.2.1]hept-5-en-3-one, A new synthetic method of this compound is introduced below., 49805-30-3

1.5. Preparation of (+-)-1-amino-4-(hydroxymethyl)-2-cyclopentene in an alcohol A 100 ml round-bottom flask fitted with magnetic stirrer was charged with 3.0 g (27.5 mmol) of (+-)-2-azabicyclo[2.2.1]hept-5-en-3-one and 1.2 g (28.3 mmol) of lithium borohydride, under an inert-gas atmosphere, in 35 g of 2-butanol, and the mixture was stirred for 3 h at 60 C. GC analysis of a sample (work-up: 0.1 g sample rendered acidic using 0.2 ml of 1M HCl, then quickly rendered basic using 0.1 ml of saturated NaHCO3) indicated the formation of the product in 12% yield after this time. (GC standard is benzophenone.)

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; Lonza AG; US2002/10360; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1943-79-9, The chemical industry reduces the impact on the environment during synthesis 1943-79-9, name is Phenyl methylcarbamate, I believe this compound will play a more active role in future production and life.

Sodium hydride (60% in oil, 228 mg, 5.7 mmol) was gradually added to a N,N-dimethylformamide (0.5 ml) solution of 5-nitroindole (0.841 g, 5.19 mmol) while stirring at room temperature; phenyl N-methylcarbamate (1.02 g, 6.74 mmol) was added thereto; and the reaction mixture was stirred overnight. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate. This was concentrated under reduced pressure; and the residue was purified by silica gel column chromatography (hexane-ethyl acetate, sequentially ethyl acetate) to yield the title compound (600 mg). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 2.88 (3H, d, J=4.4 Hz), 6.94 (1H, d, J=3.6 Hz), 8.03 (1H, d, J=3.6 Hz), 8.15 (1H, dd, J=2.4, 9.2 Hz), 8.35-8.43 (2H, m), 8.59 (1H, d, J=2.4 Hz).

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

Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 4664-01-1, name is 3,4-Pyridinedicarboximide, 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. 4664-01-1

Preparation 18 3-Aminopyridine-4-carboxylic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10% sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80 C. for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine-4-carboxylic acid (2.74 g, 57%). 1H NMR (DMSO d6) delta8.20 (s,1 H), 7.72 (d, J=5 Hz, 1 H), 7.45 (d, J=5 Hz, 1 H). The material was used without purification.

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 4664-01-1.

Reference:
Patent; Pfizer Inc; US6323208; (2001); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1520-70-3 name is Ethanesulfonamide, 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. 1520-70-3

EXAMPLE 154 N-(4-fluorobenzyl)-8-hydroxy-5-[methyl(methylsulfonyl)amino]-1,6-naphthyridine-7-carboxamide To a mixture of methyl-methanesulfonamide (1.06 g, 9.65 mmol), 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (1.21 g, 3.22 mmol), and Cu2O (0.46 g, 3.22 mmol) under an atmosphere of argon was added pyridine (25 mL) and the suspension was stirred at reflux for 16 hr. The reaction was allowed to cool to room temperature and the solvent evaporated in vacuo. The residue was treated with DMF (12 mL) and TFA (0.5 mL) and filtered to remove the solids. The filtrate was purified by reverse phase HPLC. (Waters PrePak 500 cartridge C18, Gradient elution with Water: Acetonitrile 95:5 to 5:95 with 0.1percent TFA at 75 mL/min over 45 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid. 1H NMR (d6DMSO, 400 MHz) delta 13.80 (1H, s), 9.66 (1H, t, J=6.4 Hz), 9.19 (1H, d, J=4.2 Hz), 8.62 (1H, d, J=8.4 Hz), 7.88 (1H, dd, J=8.4 and 4.2 Hz), 7.41 (2H, dd, J=8.6 and 5.7 Hz), 7.18 (2H, t, J=8.9 Hz), 4.61 (2H, d, J=6.4 Hz) 3.38 (3H, s), 3.19 (3H, s) ppm. FAB MS calcd for C18H17FN4O4S 405 (MH+), found 405.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Anthony, Neville J.; Gomez, Robert P.; Young, Steven D.; Egbertson, Melissa; Wai, John S.; Zhuang, Linghang; Embrey, Mark; Tran, LeKhanh; Melamed, Jeffrey Y.; Langford, H. Marie; Guare, James P.; Fisher, Thorsten E.; Jolly, Samson M.; Kuo, Michelle S.; Perlow, Debra S.; Bennett, Jennifer J.; Funk, Timothy W.; US2003/55071; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, Adding a certain compound to certain chemical reactions, such as: 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 402-46-0.

General procedure: A solution of compound 9, 12a-12g or 16a-16g (1.0eq),substituted sulfonyl chloride (1.1eq) or substituted acyl chloride(1.1eq) and TEA(1.5eq) were added into DMF(5 ml. And then themixture was stirred at room temperature for 6 h. Upon completion,ethyl acetate (20 ml) and H2O (5 ml) were added. The aqueous layerwas extracted with ethyl acetate for several times, the combinedorganic layers were washed with H2O for several times, and thenwashed with brine, dried over MgSO4 and evaporated to give theproducts. The crude residue was purified by silica gel columnchromatography eluted with a mixture of petroleum ether andethyl acetate (2:1) to obtain target compound.

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jian-Song; Gao, Qiu-Lei; Wu, Bo-Wen; Li, Dong; Shi, Lei; Zhu, Ting; Lou, Jian-Feng; Jin, Cheng-Yun; Zhang, Yan-Bing; Zhang, Sai-Yang; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 630-22-8 name is 2,2-Dimethylpropanethioamide, 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. 630-22-8

N-Bromosuccinimide (107mg, 0.60mmol) was added to a solution of tert-bv yl (3-(2-(2- chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)carbamate (200. Omg, 0.54mmol) in dimethylacetamide (5.5mL). The reaction mixture was stirred at room temperature for lh then 2,2,2-Trimethylthioacetamide (70mg, 0.60mmol) was added. After stirring at room temperature for lh, the medium was heated at 50C overnight. The mixture was poured onto water and the suspension was filtered. The solid was dried under vacuum to afford the title (220mg, 86%). LC/MS (ES+): 463.3-465.3 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2-Dimethylpropanethioamide, and friends who are interested can also refer to it.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

49805-30-3, 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. 49805-30-3, name is 2-Azabicyclo[2.2.1]hept-5-en-3-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.7. Preparation of (+-)-1-amino-4-(hydroxymethyl)-2-cyclopentene in the presence of additives such as water or various alcohols A 10 ml round-bottom flask was charged with 0.50 g (4.66 mmol) of (+-)-2-azabicyclo[2.2.1]hept-5-en-3-one and 0.30 g (13.7 mmol) of lithium borohydride in 7.5 ml of abs. dioxane, and the mixture was heated to 60 C. At this temperature, over the course of 30 min, X mmol of alcohol Y was added dropwise using a syringe. The mixture is then stirred for 2 h at 60 C., cooled to about 20 C. and poured into about 10 ml of semi-concentrated HCl. The content was then determined directly using a quantitative ion-chromatographic method (cf.

The synthetic route of 2-Azabicyclo[2.2.1]hept-5-en-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lonza AG; US2002/10360; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

3984-14-3,Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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 6; N’-(3-chloro-5-oxo-5H-pyridor4′,3′:4,51cycloheptarL2-^lpyridine-7-yl)-N,N-dimethylsulfamide (Compound 7); To a stirred solution of 3,7-dichloro-5H-pyrido[4′ ,3′ :4,5]cyclohepta[l,2-&]pyridin-5-one(80 mg, 0.29 mmol) in dioxane (5 mL) were added Pd2(dba)3 (13 mg, 0.014 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (25 mg, 0.043 mmol), N,N-dimethylsulfamide (36 mg, 0.29 mmol), and Cs2CO3 (0.28 g, 0.87 mmol). The reaction mixture was heated to 95 0C for 2 h, cooled to room temperature, treated with water, and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) delta 8.79 (d, IH); 8.86 (d, 1H);8.76 (s, IH); 8.66 (br s, IH); 8.54 (d, IH); 7.96 (s, IH); 7.38 (d, IH); 7.27 (d, IH); 2.99 (s, 6H). LRMS (ESI) calc’d for (C15H13ClN4O3S) [M+H]+, 365.0; found 365.1.

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

Reference:
Patent; MERCK & CO., INC.; WO2007/50401; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 3144-09-0, name is Methylsulfonamide, I believe this compound will play a more active role in future production and life. 3144-09-0

To a 50 mL three-necked flask, add 1.22 g (10.0 mmole) of benzoic acid and 12 mL of chloroform and stir at room temperature for about 5 minutes. Thereafter, the internal temperature was adjusted to around 5 C. by cooling with external cooling in an ice water bath, and then 1.484 g (5.0 mmole) of triphosgene and 3.036 g (30 mmole) of triethylamine were added in turn, (10.0 mmole) of methanesulfonamide was added thereto, and the mixture was stirred for about 5 minutes. Then, the ice water bath was removed and the temperature was raised to room temperature. While stirring for about 1 hour, the reaction was carried out by thin film chromatography (TLC) After confirming the completion of the reaction, the reaction solvent was distilled off under reduced pressure, and 15 mL of water was added to the resulting solid to dissolve the solid salt formed by the neutralization reaction of triethylamine and hydrochloric acid produced as a by-product The desired compound, acylsulfonamide, is dispersed in a solid form and stirred. After filtration, the filtrate was washed with water, and the obtained solid was dried to obtain 1.89 g (yield: 94.9%) of acyl sulfoneamide as a target compound in a solid form.

The chemical industry reduces the impact on the environment during synthesis 3144-09-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HANKYONG NATIONAL UNIV. Industry-University Cooperation Foundation; Kim Mi-su; Han Gi-jong; (8 pag.)KR2017/136043; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics