N⁵-(5-chloro-2,4-dihydroxyphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide

Base Information

• Chemical Name: N⁵-(5-chloro-2,4-dihydroxyphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide
• CAS No.: 1584301-59-6
• Molecular Formula: C₁₆H₁₇ClN₄O₅
• Molecular Weight: 380.788

Synonyms:N⁵-(5-chloro-2,4-dihydroxyphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide

Chemical Property of N⁵-(5-chloro-2,4-dihydroxyphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide

Chemical Property:

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Technology Process of N⁵-(5-chloro-2,4-dihydroxyphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide

There total 7 articles about N⁵-(5-chloro-2,4-dihydroxyphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide 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: 49.0%

N5-(5-chloro-2,4-dimethoxyphenyl)-N3-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide (1584301-84-7) → N5-(5-chloro-2,4-dihydroxyphenyl)-N3-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide (1584301-59-6)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.01.056

Reference yield:

1-acetyl-4-piperidinone (32161-06-1) → N5-(5-chloro-2,4-dihydroxyphenyl)-N3-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide (1584301-59-6)

Guidance literature:

Multi-step reaction with 7 steps

1: toluene-4-sulfonic acid / toluene / Reflux

2: triethylamine / dichloromethane

3: trifluoroacetic acid / dichloromethane / Reflux

4: hydrogenchloride / water / Reflux

5: methanol / 12 h

6: 1,4-dioxane / 60 °C

7: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

With hydrogenchloride; boron tribromide; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; water; toluene;

DOI:10.1016/j.ejmech.2014.01.056

Reference yield:

C10H12N2O4 (1584301-40-5) → N5-(5-chloro-2,4-dihydroxyphenyl)-N3-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide (1584301-59-6)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / water / Reflux

2: methanol / 12 h

3: 1,4-dioxane / 60 °C

4: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

With hydrogenchloride; boron tribromide; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1016/j.ejmech.2014.01.056

upstream raw materials:

N-ethyl-4,5,6,7-tetrahydroisoxazole[4,5-c]pyridine-3-carboxamide

5-chloro-2,4-dimethoxyphenyl isocyanate

N⁵-(5-chloro-2,4-dimethoxyphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide

1-acetyl-4-piperidinone

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