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Crystalline forms of 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

IP.com Disclosure Number: IPCOM000195722D
Publication Date: 2010-May-13
Document File: 6 page(s) / 96K

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Crystalline forms of 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline (CMEQ) of the following formula

Cl

O O

O

N

O

N

is an intermediate for the production of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4- quinazolinamine hydrochloride (referred as "ERL HCl") of the following formula

HCl

N

H

O O

O

O N

N

Crystalline forms of CMEQ were found and are described herein below.

    A crystalline form of CMEQ obtained according to example 1 is characterized by a powder XRD pattern with peaks at 6.5, 9.6, 14.4, 15.2, 15.6, 16.0, 16.9, 18.4, 19.2, 19.8 and
25.2 ± 0.2 degrees two-theta. In addition, the above crystalline form can be further characterized by XRPD pattern and peak list described on Figure 1 and table 1. Figure 1

Page 2 of 6

Intensity (cps)

2500

2000

1500

1000

500

0

5 10 15 20 25 30 35 40 45 50

2Theta (°)

Table 1

Pos. [°2Th.]

d-spacing
[A]

Rel. Int. [%]

6.5 13.5325 100.0
8.3 10.6077 0.3
9.6 9.2548 7.1
10.5 8.3892 0.3
11.3 7.7985 1.1
13.1 6.7536 3.2
14.4 6.1588 6.6
14.8 5.9957 2.3
15.2 5.8462 29.7
15.6 5.6689 7.7
16.0 5.5397 12.3
16.9 5.2418 6.0
18.4 4.8193 3.7
19.2 4.6174 15.7
19.8 4.4835 26.3
20.0 4.4439 8.0
20.8 4.2674 18.3
21.2 4.1905 10.0
21.9 4.0635 3.3
22.4 3.9605 0.7
22.8 3.8934 5.0
23.2 3.8276 9.1

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Rel. Int. [%]

23.5 3.7925 5.6
24.1 3.6863 2.3
24.4 3.6450 6.5
24.7 3.6100 3.3
24.9 3.5783 2.7
25.2 3.5347 14.4
25.8 3.4590 2.5
26.4 3.3745 2.8
26.9 3.3143 1.0
27.2 3.2777 0.8
27.6 3.2304 9.4
28.0 3.1838 1.0
29.0 3.0773 2.3
29.5 3.0273 3.7
30.0 2.9824 3.0

Pos. [°2Th.]

d-spacing
[A]

    Another crystalline form of CMEQ obtained according to example 2 is characterized by a powder XRD pattern with peaks at 4.1, 6.5, 8.2, 12.0, 13.1, 15.2, 16.0, 16.7, 19.8 and
27.6 ± 0.2 degrees two-theta. In addition, the above crystalline form can be further characterized by XRPD pattern and peak list described on Figure 2 and table 2. Figure 2

Page 4 of 6

Intensity (cps)

2500

2000

1500

1000

500

0

5 10 15 20 25 30 35 40 45 50

2Theta (°)

Table 2

Pos. [°2Th.]

d-spacing
[A]

Rel. Int. [%]

4.1 21.7535 1.0
6.5 13.5149 100.0
8.2 10.8292 1.7
9.6 9.2298 2.1
10.6 8.3851 0.5
11.4 7.7370 0.4
12.0 7.3510 1.6
13.1 6.7478 3.6
14.4 6.1506 1.8
14.8 5.9780 1.5
15.2 5.8427 54.9
15.7 5.6572 2.5
16.0 5.5357 5.5
16....