Browse Prior Art Database

A crystalline form of intermediate of 6-(3-Chloro-2-fluorobenzyl)-1-[1(S)- (hydroxymethyl)-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

IP.com Disclosure Number: IPCOM000235529D
Publication Date: 2014-Mar-06
Document File: 3 page(s) / 103K

Publishing Venue

The IP.com Prior Art Database

This text was extracted from a PDF file.
This is the abbreviated version, containing approximately 54% of the total text.

Page 01 of 3

    A crystalline form of intermediate of 6-(3-Chloro-2-fluorobenzyl)-1-[1(S)- (hydroxymethyl)-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

 

     6-(3-Chloro-2-fluorobenzyl)-1-[1(S)-(hydroxymethyl)-2-methylpropyl]-7-methoxy-4- oxo-1,4-dihydroquinoline-3-carboxylic acid referred to as Compound I, has the following chemical structure:

 

 (S)-ethyl 6-bromo-1-(1-(tert-butyldimethylsilyloxy)-3-methylbutan-2-yl)-7-methoxy- 4-oxo-1,4-dihydroquinoline-3-carboxylate referred to as Compound II is an intermediate in the preparation of Compound I. Samples of Compound II were prepared by the process described in example 1, and were analyzed by X-ray powder diffraction ("XRPD") to provide a crystalline form. Figure 1 presents the XRPD of the obtained form.

Figure 1: XRPD of crystalline Compound II 

Intensity (counts)

20000

15000

10000

5000

0

5 10 15 20 25 30 35 2Theta (°)


Page 02 of 3

    According to figure 1, the crystalline form of Compound II is characterized by XRPD peaks at: 6.6, 8.6, 9.1, 9.8, 10.6, 11.5, 12.4, 13.2, 14.1, 15.2, 15.8, 16.2, 17.3, 17.5, 18.3, 18.8,


20.7, 21.5, 22.2, 23.0, 23.7, 24.7, 25.8, 26.6, 27.2, 28.5, 31.0, 33.0 and 35.9 °2theta ± 0.2 °2theta.

Figure 2: FTIR spectrum of crystalline Compound II 

85

80

75

70

65

60

%T

55

50

45

40

35

30

25

3000

2000

1500

1000

Wavenumbers (cm-1)

XRPD method:

    Gently grounded 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 (Ǻngströ...