(Z)-methyl 3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate

Base Information

• Chemical Name: (Z)-methyl 3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate
• CAS No.: 1987887-92-2
• Molecular Formula: C₂₄H₂₁N₃O₃
• Molecular Weight: 399.449
• Mol file: 1987887-92-2.mol

Synonyms:

Chemical Property of (Z)-methyl 3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate

Chemical Property:

• Melting Point: 273 - 276°C
• Boiling Point: 641.3±55.0 °C(Predicted)
• PKA: 11.16±0.20(Predicted)
• Density: 1.316±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.0% Min ^*data from raw suppliers

(3Z)?-2,?3-Dihydro-?3-?[[[4-?(methylamino)?phenyl]?amino]?phenylmethylene]?-?2-?oxo-?1H-?Indole-?6-?carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3Z)?-2,?3-Dihydro-?3-?[[[4-?(methylamino)?phenyl]?amino]?phenylmethylene]?-?2-?oxo-?1H-?Indole-?6-?carboxylic Acid Methyl Ester is an impurity of Nintedanib (N478290), an angiokinase inhibitor and is used in the treatment of idiopathic pulmonary fibrosis. Also inhibits the process blood vessel formation which may be used to assist in cancer therapy.

Technology Process of (Z)-methyl 3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate

There total 14 articles about (Z)-methyl 3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate 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: 92.0%

C29H29N3O5 → methyl (Z)-3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (1987887-92-2)

Guidance literature:

With hydrogenchloride; In methanol; dichloromethane; at 20 ℃; for 3h;

Reference yield: 85.0%

(E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (1168152-07-5) + N-methyl-benzene-1,4-diamine (623-09-6) → methyl (Z)-3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (1987887-92-2)

Guidance literature:

(E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; N-methyl-benzene-1,4-diamine; In methanol; for 3h; Reflux;

With potassium hydroxide; In methanol; for 0.333333h;

DOI:10.1039/d1cc00354b

Reference yield:

N-methyl(p-nitroaniline) (100-15-2) → methyl (Z)-3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (1987887-92-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / isopropyl alcohol / 0.25 h / 25 °C

1.2: 3 h / 25 °C

2.1: hydrogen; palladium on activated charcoal / isopropyl alcohol / 12 h / 30 °C

3.1: acetic acid / N,N-dimethyl-formamide / 0.25 h / 20 °C

3.2: 5 h / 90 °C

4.1: hydrogenchloride / methanol; dichloromethane / 3 h / 20 °C

With hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

methyl 1-(2-chloroacetyl)-2-oxoindoline-6-carboxylate

N-chloroacetyl-3-[methoxy(phenyl)methylene]-2-oxoindoline-6-carboxylic acid methyl ester

3-[methoxy(phenyl)methylene]-2-oxoindoline-6-carboxylic acid methyl ester

methyl 3-nitro-4-chlorobenzoate

Refernces

• 1、 -. "nepal reaches Neeb process and intermediates for the synthesis of (by machine translation)". . . Retrieved 2016/11/02.