Month: November 2020

The chemical industry reduces the impact on the environment during synthesis 811442-84-9, name is tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate, I believe this compound will play a more active role in future production and life. 811442-84-9

200 mg (0.594 mmol) of tert-butyl (14-amino-3,6,9,12-tetraoxatetradec-1-yl)carbamate, 111 mg (0.713 mmol) of (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid and 410 mul (2.4 mmol) of N,N-diisopropylethylamine were dissolved in 6 ml of dimethylformamide, and 339 mg (0.892 mmol) of HATU were added. The reaction mixture was stirred at RT for 1 h and purified directly by preparative RP-HPLC (column: Reprosil 250*30; 10mu, flow rate: 50 ml/min, MeCN/water/0.1% TFA). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 130 mg (43% of theory) of tert-butyl [17-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-16-oxo-3,6,9,12-tetraoxa-15-azaheptadec-1-yl]carbamate. LC-MS (Method 1): Rt=0.71 min; MS (ESIpos): m/z=474 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 811442-84-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; CANCHO GRANDE, Yolanda; MARX, Leo; STELTE-LUDWIG, Beatrix; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (684 pag.)US2018/169256; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

563-83-7, 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. 563-83-7, name is Isobutyramide, A new synthetic method of this compound is introduced below.

A solution of 2-methylpropanamide (6.53 g, 75.0 mmol) and 2,4-bis(4- methoxyphenyl)-1 ,3-dithia-2,4-diphosphetane-2,4-disulfide (15.17 g, 37.51 mmol) in THF (100 mL) was heated to reflux for 4 h. The reaction mixture was then cooled to room temperature and poured into saturated aqueous NaHCO3 (200 mL). The mixture was extracted with ether (4 x 100 mL). The organic fractions were combined, dried over Na2SO , filtered, andconcentrated. Purification by flash column chromatography (20%EtOAc:hexanes) afforded the title compound. 4.77 g (62% yield) 1H-NMR (400 MHz, CDCI3) delta 7.63 (brs, 1 H), 6.90 (brs, 1 H), 2.88 (m, 1 H), and 1 .27 (d, 6H, J = 6.8 Hz).

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; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

3119-02-6, 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. 3119-02-6, name is 4-Cyanobenzenesulphonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-cyano benzenesulfonamide (3.8 g, 20.88 mmol, Intermediate 42 or commercial source: Combi-Blocks) in Lambda/,/V-dimethylformamide (50 mL), sodium azide (13.57 g, 208.73 mmol) and ammonium chloride (1 1.17 g, 208.78 mmol) were added at 27 C. The reaction mixture was heated to 120 C and was stirred at the same temperature for 5 h. Upon completion, the reaction mixture was cooled to 27 C, quenched with 1 N HCI (150 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous Na2S04, filtered and the filtrate was concentrated under reduced pressure. The residue was stirred with dichloromethane (10 mL) at 27 C for 30 min and filtered. The solid was dried under vacuum to afford 4-(2H-tetrazol-5- yl)benzenesulfonamide (3.2 g, 68%) as an off-white solid.1H NMR (400 MHz, DMSO-c/6) delta 8.23 (d, J = 8.5 Hz, 2H), 8.04 (d, J = 8.5 Hz, 2H), 7.53 (s, 2H). MS m/z [M-H]”=224.03.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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,
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. 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