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Solid state forms of (S)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4- d]pyrimidin-4-amine

IP.com Disclosure Number: IPCOM000238262D
Publication Date: 2014-Aug-13
Document File: 3 page(s) / 25K

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Page 01 of 3

Solid state forms of (S)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-
d]pyrimidin-4-amine

(S)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin- 1-yl)prop-2-en-1-one (referred to as Compound I) has the following structure:

N

N N N

OPh

NH2


(S)

N

O

Compound I

Described herein below, are solid state forms of (S)-3-(4-phenoxyphenyl)-1- (piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, referred to as a compound D, which is an intermediate in the process for preparing Compound I. Samples of Compound D were prepared by the processes described in examples 1 and 2, and were analyzed by X-ray powder diffraction ("XRPD") to provide amorphous and crystalline form, respectively.

Figures 1 and 2 present the XRPD of the obtained forms.

Figure 1: XRPD of amorphous Compound D

Si

600

400

200

0


6.0


10.0


14.0


18.0


22.0


26.0


30.0


34.0


38.0

Degrees two-theta



Page 02 of 3

Figure 2: XRPD of the crystalline form of Compound D

Degrees two-theta

According to figure 1, the crystalline form of Compound D is characterized by XRPD peaks at: 9.4, 13.2, 13.4, 14.2, 16.1, 17.3, 17.8, 18.8, 19.2, 21.1, 21.5, 22.9, 24.1, 24.8,
27.7 and 29.8 degrees 2-theta ±0.2 degrees 2-theta.

XRPD method

    The analyses were performed on ARL (SCINTAG) powder X-Ray diffractometer model X'TRA equipped with a solid state detector. Copper radiation of 1.5418 Å was used. Scanning parameters: range: 2-40 degrees two-theta; scan mode: continuous scan; step size: 0.05°.; and a rate of 3 deg/min. The peak at about
28.5° is attributed to silicon powder added as an internal standard. The peak positions were corrected accordingly. No correction was performed on the presented diffractograms in the figure.

Examples:

Reference example: Preparation of the starting material: tert-butyl (S)-3-(4-amino-3-

(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

[Compound C]

    A reactor of 250 mL was loaded with 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-
d]pyrimidin-4-amine [Compound A] (7 g, 0.023 mol)), tert-butyl (S)-3-

Si

1600

1200

800

400

0


2.0


6.0


10.0


14.0


18.0


22.0


26.0


30.0


34.0


38.0


Page 03 of 3

((methylsulfonyl)oxy)piperidine-1-carboxylate [Compound B] (10.96 g, 0.04 mol), cesium carbonate (22.55 g, 0.07 mol) and DMF (81 m...