N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide

Base Information

• Chemical Name: N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide
• CAS No.: 1373938-05-6
• Molecular Formula: C₂₄H₂₀F₂N₄O₃
• Molecular Weight: 450.445

Synonyms:N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide

Chemical Property of N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide

Chemical Property:

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Technology Process of N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide

There total 8 articles about N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide 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: 8.0%

N-(5-bromopyrazin-2-yl)-2,6-difluorobenzamide (1028700-78-8) + 3-(4-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-5,5-dimethylisoxazol-4(5H)-one (1373939-88-8) → N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide (1373938-05-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c01403

Reference yield:

3-Bromo-4-ethylbenzoic acid (99548-53-5) → N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide (1373938-05-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 16 h / 20 °C

2: tetrahydrofuran / 2 h / -20 - 20 °C

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C

4: pyridine; hydroxylamine hydrochloride / methanol / 12 h / Reflux

5: acetic acid; chromium(VI) oxide; sulfuric acid / water / 0.5 h / 100 °C

6: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere

7: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 24 h / 100 °C / Inert atmosphere

With pyridine; chromium(VI) oxide; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sulfuric acid; hydroxylamine hydrochloride; potassium acetate; sodium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/acs.jmedchem.1c01403

Reference yield:

2,6-difluorobenzoylchloride (18063-02-0) → N-(5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-ethylphenyl)pyrazin-2-yl)-2,6-difluorobenzamide (1373938-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 1 h / 0 - 25 °C

2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 24 h / 100 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/acs.jmedchem.1c01403

upstream raw materials:

2,6-difluorobenzoylchloride

3-Bromo-4-ethylbenzoic acid

N-(5-bromopyrazin-2-yl)-2,6-difluorobenzamide

3-(4-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-5,5-dimethylisoxazol-4(5H)-one

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