Trifluoroacetic acid → 2-(6-chloro-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

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To a stirred solution of N-tert-butyl-2-(6-chloro-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (120 mg, 240 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL). After 15 h, the mixture was concentrated in vacuo then 25 mL of a Jan. 10, 1960 mixture of ammonium hydroxide/methanol/dichloromethane added. After 1 h the mixture was concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0 to 5% of a solution of methanol containing 10% ammonium hydroxide in dichloromethane) gave 2-(6-chloro-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (50.4 mg, 57%). MS: (M+H)+=369; 1H NMR (DMSO-d6) δ: 8.97 (s, 1H), 8.57 (s, 2H), 8.43 (s, 1H), 8.00 (dd, J=8.5, 0.5 Hz, 1H), 7.61 (s, 1H), 7.41 (dd, J=8.5, 1.8 Hz, 1H), 1.50 (s, 9H).

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