Category: 5511-18-2

Electric Literature of 5511-18-2, These common heterocyclic compound, 5511-18-2, name is Adamantane-1-carboxamide, 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.

Powdered LiAlH4 (3 g, 80 mmol) was added to a stirred solution of the carboxamide in THF (120 mL) at 0 C. After warming to ambient temperature, the suspension was heated at reflux for 16 h, cooled, and saturated aqueous sodium hydroxide (20 mL) was added dropwise at 0 C with vigorous stirring. After stirring for 1 h at ambient temperature, the mixture was filtered and the residue was washed with CH2Cl2 (60 mL). The combined organic portions were dried (MgSO4) and evaporated in vacuo to give the crude amine S8 (4.1 g, 60% over 3 steps) as a colourless oil with some solid impurities. The crude was then purified by flash chromatography on silica eluting with CH2Cl2-MeOH-NH4OH (90:9:1) to give the pure amine S8 as a colourless oil; deltaH (200 MHz; CDCl3) 2.31 (2 H, s), 1.98 (3 H, br s), 1.76-1.60 (6 H, m), 1.46-1.45 (6 H, m). The spectroscopic data matched that reported by the Aldrich Library.

Statistics shows that Adamantane-1-carboxamide is playing an increasingly important role. we look forward to future research findings about 5511-18-2.

Reference:
Article; Beinat, Corinne; Banister, Samuel D.; Hoban, Jane; Tsanaktsidis, John; Metaxas, Athanasios; Windhorst, Albert D.; Kassiou, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 828 – 830;,
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. 5511-18-2, name is Adamantane-1-carboxamide, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

To a solution of admantane-1 -carboxamide (2 g, 11.17 mmol) in THF (50 mL) was added BH3. Me2S (10.2 M, 3.4 mL, 34.7 mmol) under nitrogen. The mixture was heated at reflux overnight. The solution was cooled to rt. Methanol (20 mL) was added to the solution. The mixture was concentrated under vacuum to give crude product, which was purified by chromatography on silica gel to afford (i-adamantyl)methylamine (1.09 g, 59 %). 1H NMR (CDCI3, 400 MHZ): delta=1.44-1.96 (m, 15H), 2.30 (s, 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; VITAE PHARMACEUTICALS, INC.; WO2008/106128; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 5511-18-2, 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. 5511-18-2 name is Adamantane-1-carboxamide, 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.

General procedure: To a stirred solution of 13, 10k or 10m (130 mmol) in dried THF (150 mL) cooled in an ice-waterbath was added portionwise LiAlH4 (6.41 g, 169 mmol). Thereafter the reaction mixture was stirredat room temperature for 1 h and then at reflux for another 5 h, when the reaction completed asindicated by TLC analysis. On cooling to room temperature, the reaction mixture was carefullypoured into ice-water (500 mL) while stirring, and the resulting mixture was diluted with CH2Cl2(300 mL), stirred for 0.5 h and filtered off through Celite. The organic phase was separated from thefiltrate, and the aqueous phase was back-extracted with CH2Cl2 (200 mL ¡Á 2). The combined organicphases were washed with saturated brine (200 mL), dried (Na2SO4) and evaporated on a rotaryevaporator to give a residue, which was purified by column chromatography through a short silicagel column to afford 2d, 2k or 2m. These amines were used directly in the next step without furtherpurification and characterization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Adamantane-1-carboxamide, and friends who are interested can also refer to it.

Reference:
Article; Cai, Wenqing; Wu, Jingwei; Liu, Wei; Xie, Yafei; Liu, Yuqiang; Zhang, Shuo; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong; Molecules; vol. 23; 2; (2018);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 5511-18-2, The chemical industry reduces the impact on the environment during synthesis 5511-18-2, name is Adamantane-1-carboxamide, I believe this compound will play a more active role in future production and life.

A solution of adamantanecarboxamide (1 mmol) in THF (4 mL) was treated with LiAIH4 (4 mmol) at 0 C and stirred under a N2 atmosphere whilst warming to room temperature. After 2 h, the reaction was heated at reflux for 16 h and then cooled on ice. Chilled H20 (150 pL) was added dropwise, with vigorous stirring, and then followed by aqueous sodium hydroxide (15% wiv, 150 pL) and additional water (0.5 mL). The solution was left stirring at room temperature until effervescence had ceased and the grey powder had turned white (30 min). The solution was dried (MgS04) and then filtered. The precipitate was washed with additional dichloromethane (2 x 4 mL). The filtrates in each case were combined. Purification was carried out as follows

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, Adamantane-1-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF SYDNEY; KASSIOU, Michael; FIGTREE, Gemma; O’BRIEN-BROWN, James; WILKINSON, Shane; HANSEN, Thomas; (64 pag.)WO2020/37350; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 5511-18-2, name is Adamantane-1-carboxamide, 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. 5511-18-2

Example 37 A solution of Example B13 (0.150 g, 0.837 mmol) in dioxane (10 mL) was treated with oxalyl chloride (0.150 g, 1.182 mmol), heated at 100 C. for 2 h, cooled to RT and concentrated to dryness. The residue was treated with a solution of Example A6 (0.150 g, 0.533 mmol) and pyridine (0.080 g, 1.011 mmol) in DCM (10 mL) and stirred at RT for 2 days. The mixture was concentrated to dryness, the residue treated with MeCN and the resulting solid collected via filtration and dried to afford N-((6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)adamantane-1-carboxamide (200 mg, 77%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.18 (s, 1H), 10.32 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.24 (s, 1H), 7.95 (d, J=0.7 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.83 (s, 3H), 2.25 (s, 3H), 1.98 (m, 3H), 1.89 (m, 6H), 1.66 (m, 6H); MS (ESI) m/z: 487.2 (M+H+).

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 5511-18-2.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics