Trifluoroacetic acid → 2-(6-chloro-1-((5-methylisoxazol-3-yl)methyl)-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-(6-Chloro-1-((5-methylisoxazol-3-yl)methyl)-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (89 mg, 153 μmol) was dissolved in 1,2-dichloroethane (3 mL) and placed in a sealed tube. To this was added trifluoroacetic acid (1.75 g, 1.18 mL, 15.3 mmol). The tube was sealed and the mixture heated at to 80° C. After 15 h, the mixture was cooled and concentrated in vacuo. The residue was purified by chromatography (silica, 24 g Analogix column, 95:5 dichloromethane:methanol) then preparative TLC (95:5 dichloromethane/methanol) to give 2-(6-chloro-1-((5-methylisoxazol-3-yl)methyl)-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (15 mg, 33.3 μmol, 22%). MS (M+Na)+=472; 1H NMR (CDCl3) δ: 9.37 (s, 1H), 9.22-9.32 (m, 1H), 8.42-8.51 (m, 1H), 8.34-8.40 (m, 1H), 8.11-8.21 (m, 1H), 7.56-7.63 (m, 1H), 7.19-7.36 (m, 1H), 5.90-5.97 (m, 1H), 5.63-5.75 (m, 2H), 4.38-4.56 (m, 1H), 2.38 (s, 3H), 1.41 (d, J=6.4 Hz, 6H).

Provenance & Evidence