6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one

Base Information

• Chemical Name: 6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one
• CAS No.: 1242157-65-8
• Molecular Formula: C₃₆H₃₇FN₆O₃
• Molecular Weight: 620.727
• Mol file: 1242157-65-8.mol

Synonyms:6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one

Chemical Property of 6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one

There total 11 articles about 6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one 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: 27.0%

2-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinoline-1(2H)-one (1242156-55-3) + 3-{[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino}-1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one (1293344-24-7) → 6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one (1242157-65-8)

Guidance literature:

With potassium phosphate; XPhos; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In water; butan-1-ol; at 100 ℃; for 1.5h; Inert atmosphere of argon;

Reference yield:

6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one (1242157-15-8) → 6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one (1242157-65-8)

Guidance literature:

Multi-step reaction with 5 steps

1: tricyclohexylphosphine; palladium diacetate; potassium phosphate / toluene; water / 4 h / 100 °C / Inert atmosphere

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere; Sealed tube

3: caesium carbonate; copper(l) iodide / 1,4-dioxane / 18 h / Inert atmosphere; Sealed tube; Heating

4: alkali borohydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5: bis(dibenzylideneacetone)-palladium⁽⁰⁾; potassium phosphate; XPhos / water; butan-1-ol / 1.5 h / 100 °C / Inert atmosphere

With potassium phosphate; copper(l) iodide; palladium diacetate; caesium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis(dibenzylideneacetone)-palladium⁽⁰⁾; XPhos; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; water; toluene; butan-1-ol; 1: |Suzuki Coupling / 5: |Suzuki Coupling;

DOI:10.1021/jm500305p

Reference yield:

6-cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one (1242157-16-9) → 6-cyclopropyl-2-(3-{5-[5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-hydroxymethylphenyl)-8-fluoro-2H-isoquinolin-1-one (1242157-65-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere; Sealed tube

2: caesium carbonate; copper(l) iodide / 1,4-dioxane / 18 h / Inert atmosphere; Sealed tube; Heating

3: alkali borohydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4: bis(dibenzylideneacetone)-palladium⁽⁰⁾; potassium phosphate; XPhos / water; butan-1-ol / 1.5 h / 100 °C / Inert atmosphere

With potassium phosphate; copper(l) iodide; caesium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis(dibenzylideneacetone)-palladium⁽⁰⁾; XPhos; In tetrahydrofuran; 1,4-dioxane; water; butan-1-ol; 4: |Suzuki Coupling;

DOI:10.1021/jm500305p

upstream raw materials:

2-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinoline-1(2H)-one

3-{[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino}-1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one

6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one

6-cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one