N₃-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide

Base Information

• Chemical Name: N₃-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide
• CAS No.: 1256382-59-8
• Molecular Formula: C₂₆H₃₂N₂O₂
• Molecular Weight: 404.552

Synonyms:N₃-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide

Chemical Property of N₃-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide

Chemical Property:

Purity/Quality:

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Technology Process of N₃-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide

There total 5 articles about N₃-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

rimantadine (13392-28-4,117857-51-9,117857-52-0,129277-01-6) + 1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxylic acid (71575-95-6) → N3-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide (1256382-59-8)

Guidance literature:

1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxylic acid; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

rimantadine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

Reference yield:

ethyl 1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxylate (1256382-33-8) → N3-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide (1256382-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / ethanol / 6 h / Reflux

1.2: pH 2

2.1: benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C

2.2: 12 h / 20 °C

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm100286k

Reference yield:

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6,51145-57-4) → N3-(1-(1-adamantyl)ethyl)-1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxamide (1256382-59-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C

1.2: 0.75 h / 20 °C

2.1: acetic acid / ethanol / 5 °C / Reflux

3.1: sodium hydroxide / ethanol / 6 h / Reflux

3.2: pH 2

4.1: benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C

4.2: 12 h / 20 °C

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm100286k

upstream raw materials:

rimantadine

1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxylic acid

ethyl 1-ethyl-4-oxo-6-phenyl-1,4-dihydropyridine-3-carboxylate

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate

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