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

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Reaction Steps

To a stirred solution of N-tert-butyl-2-(3-chloro-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.1 g, 200 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, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane) gave 2-(3-Chloro-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (28 mg, 38%). MS (M−H)−=367; 1H NMR (DMSO-d6) δ: 8.96 (s, 1H), 8.62 (d, J=8.8 Hz, 1H), 8.44 (s, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.70 (ddd, J=8.4, 7.2, 1.0 Hz, 1H), 7.61 (s, 1H), 7.47-7.54 (m, 1H), 1.50 (s, 9H).

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