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

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CAS:1139453-98-7
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N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide manufacturers
N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide Basic information
Product Name:N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide
Synonyms:Nidanib Impurity 12: N-methyl-2- (4-methylpiperazin-1-yl) -N- (4-nitrophenyl) -acetamide;N-Methyl-2-(4-methyl-1-piperazinyl)-N-(4-nitrophenyl)acetamide;N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide;N,4-Dimethyl-N-(4-nitrophenyl)-1-piperazineacetamide;Nintedanib impurity 2/N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide;Nintedanib Intermediate 1;Intedanib Impurity 12;Nintedanib-003
CAS:1139453-98-7
MF:C14H20N4O3
MW:292.33
EINECS:
Product Categories:Intermediate of BIBF-1120 and PKI587
Mol File:1139453-98-7.mol
N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide Structure
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)
pka7.43±0.10(Predicted)
form Solid
color Pale Yellow to Light Yellow
Safety Information
MSDS Information
N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide Usage And Synthesis
UsesN-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
1-Methylpiperazine

109-01-3

2-CHLORO-N-METHYL-N-(4-NITROPHENYL)ACETAMIDE

2653-16-9

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

1139453-98-7

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: WO2009/71523, 2009, A1. Location in patent: Page/Page column 4; 23-24
[3] Patent: WO2009/71523, 2009, A1. Location in patent: Page/Page column 4; 24
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2015, vol. 58, # 7, p. 308 - 312
Tag:N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)acetamide(1139453-98-7) Related Product Information
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