Trifluoroacetic acid → 2-(5-chloro-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)amide

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Reaction Steps

2-(5-Chloro-1H-indazol-1-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (124 mg, 241 μmol) was dissolved in dichloromethane (3 mL) then trifluoroacetic acid (1 mL) added. After 15 h the mixture was concentrated in vacuo and Jan. 10, 1960 ammonium hydroxide/methanol/dichloromethane solution (25 mL) added. After 1 h the mixture was concentrated in vacuo and purified by chromatography (silica, 24 g Analogix column, 0-4% of methanol containing 10% ammonium hydroxide in dichloromethane) to give 2-(5-chloro-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)amide (57.7 mg, 62%) as a solid. MS (M+H)+=385; 1H NMR (DMSO-d6) δ: 9.04 (s, 1H), 8.70 (d, J=9.0 Hz, 1H), 8.53 (s, 1H), 8.43 (s, 1H), 8.07 (d, J=1.5 Hz, 1H), 7.63 (s, 1H), 7.60 (d, J=2.1 Hz, 1H), 3.59 (d, J=5.7 Hz, 2H), 1.44 (s, 6H).

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