1139453-98-7

Basic information

• Product Name: N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide
• Synonyms: N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide;N,4-Dimethyl-N-(4-nitrophenyl)-1-piperazineacetamide;Nintedanib Intermediate 1;Intedanib Impurity 12
• CAS NO: 1139453-98-7
• Molecular Formula: C₁₄H₂₀N₄O₃
• Molecular Weight: 292
• Product Categories: Intermediate of BIBF-1120 and PKI587
• Mol File: 1139453-98-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 446.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.230
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.43±0.10(Predicted)
• CAS DataBase Reference: N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide(1139453-98-7)
• EPA Substance Registry System: N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide(1139453-98-7)

Safety Data

• Hazardous Substances Data: 1139453-98-7(Hazardous Substances Data)

Usage

Uses

N-Methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide is used as a reactant in the synthetic preparation of 6-methoxycarbonyl-substituted indolinones, such as Intedanib (I666650), which is a triple angiokinase inhibitor and antitumor agent.

Upstream product

• 586-78-7 para-nitrophenyl bromide 
• 100-15-2 N-methyl(p-nitroaniline) 
• 109-01-3 1-methyl-piperazine 
• 23543-31-9 2-bromo-N-methyl-N-(4-nitrophenyl)acetamide 
• 2653-16-9 2-chloro-N-methyl-N-(4-nitrophenyl)acetamide 

Downstream Products

• 262368-30-9 N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine 
• 656247-18-6 methyl (3Z)-3-[({4-[N-methyl-2-(4-methylpiperazin-1-yl)acetamido]phenyl}amino)(phenyl)methylidene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylate ethanesulfonate salt 
• 1160294-26-7 nintedanib 

Relevant articles and documents

Design, synthesis and biological evaluation of deuterated nintedanib for improving pharmacokinetic properties

Nintedanib is a novel triple angiokinase inhibitor that inhibits three growth factors simultaneously. Deuterated derivatives of nintedanib at certain metabolically active sites were prepared and evaluated in vitro and in vivo. In particular, deuterated compound SKLB-C2202 had significantly improved pharmacokinetic properties compared with nintedanib. These efforts lay the foundation for further investigating the druggability of SKLB-C2202. Deuterated derivatives of nintedanib at certain metabolically active sites were prepared and evaluated in vitro and in vivo. Deuterated compound SKLB-C2202 had significantly improved pharmacokinetic properties compared with nintedanib. Further research is underway.

Preparation method of amino intermediate (by machine translation)

Compared with an existing preparation method, the method for preparing. the amine-based (I) intermediate disclosed by the invention comprises the following, steps: carrying (III) out condensation, reduction and the like of the compound of. the formula I to obtain, the target compound (I), and 1 remarkably reducing the, content of the impurities in the obtained compound according to the, invention as compared with the existing preparation. method. (by machine translation)

Method for preparing Nintedanib,I intermediate through one-pot method

The invention relates to a method for preparing Nintedanib,I key intermediate N-(4-aminophenyl)-N-methyl-2-(4-methyl piperazine-1-group)acetamide through a one-pot method. The method comprises the steps that according to the technical scheme, N-methyl-4-nitroaniline is dissolved in an aqueous solution of an organic solvent and alkali, mixing is carried out, then chloroacetyl chloride or bromoacetyl bromide is dropwise added, and a first-stage reaction is carried out for 0.1-3 hours at the temperature of 0-70 DEG C; a water layer is removed, N-methyl piperazine is added, a second-stage reactionis carried out, and reacting is carried out for 2-10 hours at the temperature of 0-75 DEG C; then a reducing reagent is added, a third-stage reaction is carried out for 8-36 hours at the temperatureof 0-75 DEG C and the pressure of 15-100 psi. After the reaction is finished, filtering is carried out to remove the reducing reagent, the reaction liquid is condensed, a reverse phase solvent is added, crystallization is carried out, and the Nintedanib,I key intermediate N-(4-aminophenyl)-N-methyl-2-(4-methyl piperazine-1-group)acetamide (formula B) is obtained. According to the preparation method, the raw materials are easy to obtain, the process is simple, and the method is economical, environmentally friendly and suitable for industrial production.