N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide Chemical Properties

Melting point:

94 - 96°C

Boiling point:

446.9±40.0 °C(Predicted)

Density 

1.230

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

7.43±0.10(Predicted)

form 

Solid

color 

Pale Yellow to Light Yellow

N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide Usage And Synthesis

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.

Synthesis

General procedure for the synthesis of N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide from N-methylpiperazine and 2-chloro-N-methyl-N-(4-nitrophenyl)acetamide: 1-methylpiperazine (7.2 mL, 65 mmol) and potassium carbonate (13.8 g, 100 mmol) were dissolved in acetone (200 mL) and subsequently 2-chloro-N-methyl-N-(4-nitrophenyl)acetamide (11.4 g, 50 mmol) was added slowly. The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the precipitate was removed by filtration and the filtrate was rotary evaporated to remove the solvent. The residue was dissolved in ethyl acetate (50 mL × 3) and extracted with 20 mL of water. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to give 15 g of the target compound. LC-MS analysis showed m/z = 293 ([M+H]+).

References

[1] Patent: WO2009/71524, 2009, A2. Location in patent: Page/Page column 21-22; 13
[2] Patent: WO2009/71524, 2009, A2. Location in patent: Page/Page column 21-22; 13
[3] Patent: WO2009/71523, 2009, A1. Location in patent: Page/Page column 4; 23-24
[4] Patent: WO2009/71523, 2009, A1. Location in patent: Page/Page column 4; 24
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2015, vol. 58, # 7, p. 308 - 312

N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide(1139453-98-7)Related Product Information

• 2-OXO-2,3-DIHYDRO-1H-INDOLE-6-CARBOXYLIC ACID
• N-methyl-N-(4-nitrophenyl)-2-(piperazin-1-yl)acetamide
• Methyl oxindole-5-carboxylate
• Nintedanib
• N-methyl-N-(4-nitrophenyl)-2-(piperazin-1-yl)acetamide
• Methyl 1-acetyl-2-oxoindoline-6-carboxylate
• N-(4-aMinophenyl)-2-chloro-N-MethylacetaMide
• 1-Chloro-4-(trimethoxymethyl)benzene
• 1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester
• BIBF 1202
• Nintedanib Ethanesulfonate Salt
• 1,3-DiMethyl 2-[4-(Methoxycarbonyl)-2-nitrophenyl]propanedioate
• N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide
• 2-broMo-N-Methyl-N-(4-nitrophenyl)acetaMide
• 2-CHLORO-N-METHYL-N-(4-NITROPHENYL)ACETAMIDE
• BIBF-1120
• (3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester
• (Z)-methyl 3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate