TABLE 5

NMR data of deferasirox The C atoms are listed in descending order of the 13C shifts. For NMR, the carbon atoms were numbered systematically from C-1 to C-24, as shown in Fig. 7.

C Atom
Atom
13C Shifta
Carbon Multiplicity from 13C- and 2D 1H, 13C-COSY (HSQC) Spectrum
1H Shifta and 1H, 13C-COSY (HSQC)b Correlations
1H Multiplicity
1H-1H COSY Correlationsc
1H, 13C Long-Range Correlations from HMBC Spectrum, 1H Shifts,d
ppm ppm
24 C 166.4 Cq 7.98
3 C 159.9 Cq 8.04
13 C 156.3 Cq 10.78/8.04/7.37
19 C 155.2 Cq 7.39
5 C 152.0 Cq 7.54
6 C 141.1 Cq 7.98
21 C 132.5 CH 7.39 t 6.98/6.86
15 C 131.4 CH 7.37 td 7.00/7.02
23 C 131.0 CH 7.54 dd 6.98
9 C 130.6 Cq 7.55
8/10 C 130.3 CH 7.98 dm 7.55
17 C 126.7 CH 8.04 dd 7.00
7/11 C 123.3 CH 7.55 dm 7.98
16 C 119.7 CH 7.00 t 8.04/7.37
22 C 119.4 CH 6.98 t 7.54/7.39
14 C 117.0 CH 7.02 d 7.37 10.78
20 C 116.1 CH 6.86 d 7.39
18 C 114.4 Cq 6.86
12 C 113.6 Cq 10.78
13-OH 10.78 s
19-OH 10.04 sbr
COOH
13.19
sbr

  • s, singlet; d, doublet; t, triplet; q, quartet; br, broad

  • ↵ a Chemical shift reference; internal to the middle line of the DMSO-d6 NMR solvent signal: 1H: δ = 2.500 ppm; 13C: δ = 39.52 ppm; concentration: 30 mg in 0.7 ml of DMSO-δ6

  • ↵ b 1H, 13C-COSY HSQC experiment: heteronuclear correlated spectroscopy. Heteronuclear single quantum coherence experiment with 1H detection, z-gradient, and echo-antiecho sensitivity enhancement (Palmer et al., 1991; Kay et al., 1992; Schleucher et al., 1994)

  • ↵ c 1H, 1H-COSY: homonuclear correlated spectroscopy. Magnitude experiment with z-gradient (Hurd, 1990); von Kienlin et al., 1991)

  • ↵ d Long-range 1H, 13C-COSY, HMBC experiment: heteronuclear correlated spectroscopy. Heteronuclear multiple bond correlation experiment with 1H detection and z-gradient (Bax et al., 1986; Willker et al., 1993)