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

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To a stirred solution of N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.13 g, 219 μmol) in dichloromethane (2 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 4% of a solution of methanol containing 10% ammonium hydroxide in dichloromethane) gave 2-(1H-pyrrolo[2,3-c]pyridin-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (11 mg, 15%). MS: (M+H)+=335; 1H NMR (DMSO-d6) δ: 9.25 (s, 1H), 8.43 (d, J=3.0 Hz, 1H), 8.28 (d, J=5.3 Hz, 1H), 7.96 (s, 1H), 7.65-7.69 (m, 2H), 6.65 (dd, J=2.9, 1.9 Hz, 1H), 1.46 (s, 8H).

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