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Crystalline intermediates of (3Z)-2,3-dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl) acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-1H-indole-6-carboxylic acid methyl ester

IP.com Disclosure Number: IPCOM000241684D
Publication Date: 2015-May-21
Document File: 5 page(s) / 471K

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  Crystalline intermediates of (3Z)-2,3-dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl) acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-1H-indole-6-carboxylic acid methyl ester

    1-acetyl-3-(methoxyphenylmethylene)-2,3-dihydro-2-oxo -1H-indole-6-carboxylic acid methyl ester (referred to as Compound 1) has the following structure:

O O

    N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (referred to as Compound 2) has the following structure:

    Compound 1 and Compound 2 are intermediates in the synthesis of (3Z)-2,3-dihydro-3-[[[4- [methyl[2-(4-methyl-1-piperazinyl) acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-1H- indole-6-carboxylic acid methyl ester.

Disclosed hereinafter are crystalline forms of Compound 1 and Compound 2.

O

O

N

O


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Compound 1 crystalline form

Figure 1. PXRD pattern of crystalline Compound 1:

Intensity (counts)

160000

90000

40000

10000

0

5

10

15

20

25

30

35

2Theta (°)

List of main PXRD peaks: 7.5, 9.0, 13.5, 15.0, 15.8, 16.9, 18.0, 18.8, 20.0, 21.8.

Figure 2. FTIR spectrum of crystalline Compound 1:


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Compound 2 crystalline form

N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide Figure 3. PXRD pattern of crystalline Compound 2:

Intensity (counts)

14000

12000

10000

8000

6000

4000

2000

0

5

10

15

20

25

30

35

2Theta (°)

List of XRD peaks: 7.0, 9.9, 10.9, 14.0, 14.7, 15.7, 17.8, 20.4, 21.1, 22.2.

Figure 4. FTIR spectrum of crystalline Compound 2:


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Experimental:

PXRD method:

After being powdered using mortar and pestle, samples were applied directly on a silicon plate holder. The X-ray powder diffraction pattern was measured with a Philips X'Pert PRO X-ray powder diffractometer, equipped with a Cu irradiation source = 1.54184 Ǻ (Ǻngström), X'Celerator
(2.022º 2θ) detector. Scanning parameters: angle ra...