methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate

Base Information

• Chemical Name: methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate
• CAS No.: 1185281-09-7
• Molecular Formula: C₂₄H₂₃N₅O₄
• Molecular Weight: 445.478
• Mol file: 1185281-09-7.mol

Synonyms:methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate

Chemical Property of methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate

There total 17 articles about methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate 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:

(E)-1-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-2-hydroxyguanidine (1185855-70-2) + 1,1-cyclopropanedicarboxylic acid monomethyl ester (113020-21-6) → methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate (1185281-09-7)

Guidance literature:

With sodium sulfate; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 - 100 ℃;

Reference yield:

2-(2-methyl-5-nitrophenyl)acetonitrile (409082-11-7) → methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate (1185281-09-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: water; potassium hydroxide / methanol / 14 h / Reflux

2.1: hydrogenchloride / 1,4-dioxane / 14 h / Reflux

2.2: pH > 12

3.1: hydrogen / palladium 10% on activated carbon / ethanol / 16 h / 20 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C

5.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine / 1,4-dioxane; toluene / 0.17 h / 150 °C / Microwave irradiation

6.1: potassium acetate / methanol / 0 - 20 °C

7.1: hydroxylamine / ethanol; water / 12 h / 20 °C

8.1: sodium sulfate; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 - 100 °C

With hydrogenchloride; water; hydrogen; hydroxylamine; potassium acetate; potassium carbonate; sodium sulfate; N-ethyl-N,N-diisopropylamine; HATU; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; triphenylphosphine; In 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

Reference yield:

6-chloro-4-(methylamino)pyridine-3-carbaldehyde (449811-29-4) → methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate (1185281-09-7)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine / 1,4-dioxane; toluene / 0.17 h / 150 °C / Microwave irradiation

3: potassium acetate / methanol / 0 - 20 °C

4: hydroxylamine / ethanol; water / 12 h / 20 °C

5: sodium sulfate; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 - 100 °C

With hydroxylamine; potassium acetate; potassium carbonate; sodium sulfate; N-ethyl-N,N-diisopropylamine; HATU; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; In 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(E)-1-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-2-hydroxyguanidine

1,1-cyclopropanedicarboxylic acid monomethyl ester

2-(2-methyl-5-nitrophenyl)acetonitrile

6-chloro-4-(methylamino)pyridine-3-carbaldehyde

Downstream raw materials:

3-(5-(5-(1-(hydroxymethyl)cyclopropyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one