Ningetinib

Base Information

• Chemical Name: Ningetinib
• CAS No.: 1394820-69-9
• Molecular Formula: C₃₁H₂₉FN₄O₅
• Molecular Weight: 556.593
• Mol file: 1394820-69-9.mol

Synonyms:N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Chemical Property of Ningetinib

Chemical Property:

• PKA: 11.00±0.70(Predicted)
• Density: 1.348±0.06 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

Ningetinib 99.79% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ningetinib, is a potent, orally bioavailable small molecule tyrosine kinase inhibitor (TKI) with IC50s of 6.7, 1.9 and <1.0 nM for c-Met, VEGFR2 and Axl, respectively.

Technology Process of Ningetinib

There total 7 articles about Ningetinib 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:

3-(benzyloxy)aniline (1484-26-0) → N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (1394820-69-9)

Guidance literature:

Multi-step reaction with 8 steps

1: ethanol / 1 h / Reflux

2: 1,2-dichloro-benzene / 5 h / Reflux

3: trichlorophosphate / toluene / 1 h / 120 °C

4: N-ethyl-N,N-diisopropylamine / toluene / 12 h / 115 °C

5: hydrogenchloride; water / 1,4-dioxane / 24 h / 100 °C

6: sodium hydroxide / water; tetrahydrofuran / 10 h / 20 - 45 °C

7: potassium formate / 5%-palladium/activated carbon / water; tetrahydrofuran / 5 h / 45 °C

8: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 41 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; water; potassium formate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trichlorophosphate; 5%-palladium/activated carbon; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; 1,2-dichloro-benzene; toluene;

Reference yield:

5-((3-(benzyloxy)phenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (909345-85-3) → N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (1394820-69-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1,2-dichloro-benzene / 5 h / Reflux

2: trichlorophosphate / toluene / 1 h / 120 °C

3: N-ethyl-N,N-diisopropylamine / toluene / 12 h / 115 °C

4: hydrogenchloride; water / 1,4-dioxane / 24 h / 100 °C

5: sodium hydroxide / water; tetrahydrofuran / 10 h / 20 - 45 °C

6: potassium formate / 5%-palladium/activated carbon / water; tetrahydrofuran / 5 h / 45 °C

7: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 41 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; water; potassium formate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trichlorophosphate; 5%-palladium/activated carbon; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1,2-dichloro-benzene; toluene;

Reference yield:

7-(benzyloxy)quinolin-4-ol (749922-34-7) → N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (1394820-69-9)

Guidance literature:

Multi-step reaction with 6 steps

1: trichlorophosphate / toluene / 1 h / 120 °C

2: N-ethyl-N,N-diisopropylamine / toluene / 12 h / 115 °C

3: hydrogenchloride; water / 1,4-dioxane / 24 h / 100 °C

4: sodium hydroxide / water; tetrahydrofuran / 10 h / 20 - 45 °C

5: potassium formate / 5%-palladium/activated carbon / water; tetrahydrofuran / 5 h / 45 °C

6: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 41 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; water; potassium formate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trichlorophosphate; 5%-palladium/activated carbon; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;

upstream raw materials:

3-(benzyloxy)aniline

7-(benzyloxy)quinolin-4-ol

7-(benzyloxy)-4-chloroquinoline

5-((3-(benzyloxy)phenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Downstream raw materials:

N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide p-toluenesulfonic acid

N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide hydrochloride

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