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Crystalline form of 5-Chloro-N2-[2-isopropoxy-5-methyl-4-(4-piperidinyl)phenyl]-N4-[2-(isopropylsulfonyl)phenyl]-2,4-pyrimidinediamine

IP.com Disclosure Number: IPCOM000239900D
Publication Date: 2014-Dec-11
Document File: 3 page(s) / 138K

Publishing Venue

The IP.com Prior Art Database

Abstract

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               Crystalline form of 5-Chloro-N2-[2-isopropoxy-5-methyl-4-(4-piperidinyl)phenyl]-N4-[2- (isopropylsulfonyl)phenyl]-2,4-pyrimidinediamine

Disclosed hereinafter is a crystalline form of 5-Chloro-N2-[2-isopropoxy-5-methyl-4- (4-piperidinyl)phenyl]-N4-[2-(isopropylsulfonyl) phenyl]-2,4-pyrimidinediamine (referred herein as compound I).

Figure 1: a powder XRPD pattern of crystalline compound I:

Intensity (counts)

40000

22500

10000

2500

0

5

10

15

20

25

30

35

2Theta (°)

XRPD peaks: 7.2, 8.0, 10.7, 13.4, 14.3, 16.8, 17.7, 18.4, 18.9, 21.0degrees two theta ± 0.2 degrees two theta.

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 range: 3-40 deg., step size 0.0167, time per step 37 s, continuous scan. The accuracy of peak positions was defined as +/- 0.2 degrees due to experimental differences like instrumentations and sample preparations.


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Example 1: preparation of crystalline compound I

Step A: To a 3-neck round bottom flask (100 mL) equipped with a thermometer, mechanical stirrer and reflux condenser 2-isopropoxy-5-mehyl-4-(piperdin-4- yl)aniline dihydrochloride (5.0 g) and 2,5-dichloro-N-(2-(isopropyl sulfonyl) phenyl)pyrimidin-4-amine (5.6 g) were added. 50 mL of 2-propanol (2-PrOH) was added and mixture was heated at reflux temperature and stirred for 17 hours. The reaction mixture was then cooled to room temperature and stirred at room temperature for 2 hours. The resulting solid was filtered, washed with 3x15 mL of 2-PrOH and vacuum dried at 50°C for 3 hours.

8.79 g of 5-chloro-N2-[2-isopropoxy-5-methyl-4-(4-piperidinyl)phenyl...