Hydrochloric Acid → 6-Chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2-pyridinamine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C)[CH:5]=[C:4]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14](S(C3C=CC=CC=3)(=O)=O)[CH:13]=2)[CH:3]=1.Cl>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:3]=1Participants
4
Procedure
A mixture of Example 91a (186.0 mg, 0.436 mmol) and HCl (0.20 mL, 6.6 mmol) in ethanol (6 mL) was heated at 95° C. for 3 hours and cooled. Half of the solvent was evaporated; the resulting suspension was filtered and washed with EtOH. The solids were stirred in saturated NaHCO3 for 30 minutes, filtered, washed with water, and oven-dried to give 72.2 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 6.30 (s, 2H), 6.85 (s, 1H), 6.91 (s, 1H), 7.15 (m, 1H), 8.12 (s, 1H), 8.21-8.36 (m, 2H), 12.15 (s, brd, 1H). MS (ESI+) m/z 244.8 (M+H)+.