1H NMR assignments for delavirdine, its metabolite MET-10, and synthetic standard4-a
| Proton | MET-104-b | U-963644-b | U-96364 + TEA4-b | [13C3]Delavirdine4-c |
|---|---|---|---|---|
| Indole Ring | ||||
| H-3 | 6.914-d(dd, 0.4H, 2JC2-H3 = 7.5 Hz,1JC3-H3 = 175 Hz) | 7.12 (s, 1H) | 6.94 (s, 1H) | 6.86 (dd, 1H, 2JC2-H3 = 8 Hz,1JC3-H3 = 176 Hz) |
| 6.91 (s, 0.6H) | ||||
| H-4 | 7.47 (d, 1H, J4-6 = 2.0 Hz) | 7.55 (d, 1H, J4-6 = 2.1 Hz) | 7.49 (d, 1H, J4-6 = 2.1 Hz) | 7.49 (d, 1H, J4-6 = 1.9 Hz) |
| H-6 | 7.10 (dd, 1H, J6-4 = 2.0 Hz, J6-7 = 8.6 Hz) | 7.20 (dd, 1H, J6-4 = 2.1 Hz, J6-7 = 8.8 Hz) | 7.10 (dd, 1H, J6-4 = 2.1 Hz, J6-7 = 8.8 Hz) | 7.11 (dd, 1H, J6-4 = 2.0 Hz, J6-7 = 8.7 Hz) |
| H-7 | 7.37 (d, 1H, J7-6 = 8.6 Hz) | 7.42 (d, 1H, J7-6 = 8.8 Hz) | 7.39 (d, 1H, J7-6 = 8.8 Hz) | 7.40 (d, 1H, J7-6 = 8.7 Hz) |
| Pyridine Ring | ||||
| H-4′ | 7.37 (d, 1H, J4′-5′ = 8.0 Hz) | |||
| H-5′ | 7.27 (dd, 1H, J5′-4′ = 8.0 Hz, J5′-6′ = 5.5 Hz) | |||
| H-6′ | 7.64 (dd, 1H, J6′-4′ = 1.2 Hz, J6′-5′ = 5.5 Hz) | |||
| Piperazine Ring | ||||
| CH2N | 4.02 (br s, 4H) | |||
| CH2N | 3.30 (br s, 4H) | |||
| Isopropyl Chain | ||||
| CH | 3.70 (m, 1H) | |||
| CH3 | 1.20 (d, 6H) | |||
| Methylsulfonamido | ||||
| CH3SO2NH | 2.88 (s, 3H) | 2.90 (s, 3H) | 2.88 (s, 3H) | 2.87 (s, 3H) |
↵4-a Abbreviations: br s, broad singlet; d, doublet, dd, doublet of doublets; J, coupling constant in Hz;1J, one-bond coupling constant; 2J, 2-bond coupling constant; m, multiplet; s, singlet, t, triplet; TEA, triethylamine.
↵4-b In methanol-d4, chemical shift δ in ppm relative to methanol.
↵4-c In DMSO-d6, chemical shift δ in ppm relative to DMSO.
↵4-d Resonance consisted of a doublet at 7.09 ppm integrating for 0.2 protons and another doublet at 6.74 ppm integrating for 0.2 protons.