Trifluoroacetic acid → HCID 18367784, compound

Participants

Reaction Steps

2-[4-(tert-Butoxycarbonyl)aminopyridine-2-carbonyl]-6-chloro-3-(propionylamino)indole (step 4, 118 mg, 0.266 mmol) was treated with trifluoroacetic acid (4 ml) at room temperature for 1 h. The mixture was concentrated and azeotroped with toluene to give an oily residue. The residue was basified with saturated aqueous sodium bicarbonate (30 ml) and extracted with dichloromethane (30 ml×3). The organic phase was dried (K2CO3), and concentrated to afford the free base of title compound. The free base was dissolved in 10% HCl—MeOH (4 ml) and then evaporated. The residue obtained was crystallized from ethanol-diethyl ether to give the title compound. m.p.: 199-204° C. (decomposition) 1H-NMR (DMSO-d6) δ: 12.03 (1 H, br s), 10.41 (1 H, br s), 8.17 (1 H, d, J=7.3 Hz), 7.93 (1 H, d, J=8.9 Hz), 7.48 (1 H, d, J=1.6 Hz), 7.18 (1 H, dd, J=1.6, 8.7 Hz), 7.12 (1 H, d, J=1.8 Hz), 6.88 (1H, dd, J=7.4, 2.0 Hz), 2.18 (1 H, q, J=7.4 Hz), 0.82 (3 H, t, J=7.4 Hz).

Provenance & Evidence