7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide

Base Information

• Chemical Name: 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide
• CAS No.: 1351945-22-6
• Molecular Formula: C₂₄H₁₈F₃N₃O₃
• Molecular Weight: 453.42

Synonyms:7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide

Chemical Property of 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide

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Technology Process of 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide

There total 7 articles about 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-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: 68.0%

7-formyl-1-methyl-4-oxo-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide (1351945-26-0) → 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide (1351945-22-6)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/ml200252b

Reference yield:

4-Amino-2-chloropyridine (14432-12-3) → 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide (1351945-22-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 20 h / 120 °C

1.2: 1 h / 220 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

3.1: potassium hydroxide / water / 0.25 h / 90 °C

4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 8 h / 40 - 50 °C

5.1: bis(tri-t-butylphosphine)palladium⁽⁰⁾; cesium fluoride / 1,4-dioxane / 2.16 h / 95 °C / Inert atmosphere

6.1: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 2 h / 50 °C

7.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 0 °C

With sodium periodate; osmium(VIII) oxide; bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; lithium tri-t-butoxyaluminum hydride; triethylamine; cesium fluoride; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/ml200252b

Reference yield:

7-chloro-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide (1351945-24-8) → 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide (1351945-22-6)

Guidance literature:

Multi-step reaction with 3 steps

1: bis(tri-t-butylphosphine)palladium⁽⁰⁾; cesium fluoride / 1,4-dioxane / 2.16 h / 95 °C / Inert atmosphere

2: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 2 h / 50 °C

3: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 0 °C

With sodium periodate; osmium(VIII) oxide; bis(tri-t-butylphosphine)palladium⁽⁰⁾; lithium tri-t-butoxyaluminum hydride; cesium fluoride; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/ml200252b

upstream raw materials:

4-Amino-2-chloropyridine

7-chloro-1-methyl-4-oxo-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid

7-chloro-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-1,6-naphthyridine-3-carboxamide

1-methyl-4-oxo-N-(2-(trifluoromethyl)biphenyl-4-yl)-7-vinyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide

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