Trifluoroacetic acid → 2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide

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A solution of crude 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide (70 mg, 0.134 mmol), 2 mL of dichloromethane and 2 mL of trifluoroacetic acid was stirred 1 h, then concentrated to a yellow solid. The solid was dissolved in 2 mL of dichloromethane and 1 mL of ethylenediamine, and the yellow solution was stirred 30 min. Water (20 mL) was added. The resultant precipitate was isolated by Buchner filtration, rinsing well with water then dichloromethane, and dried by air then in vacuo to afford 33 mg (56%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide as a pale yellow solid. MS: (M+Na)+=417; 1H NMR (300 MHz, DMSO-d6) δ ppm 9.10 (s, 1 H), 8.46 (d, J=8.69 Hz, 1H), 8.42 (s, 1H), 8.14 (d, J=7.93 Hz, 1H), 8.00 (d, J=1.51 Hz, 1H), 7.27 (dd, J=8.50, 1.70 Hz, 1H), 4.17 (s, 3H), 3.55-3.70 (m, 1H), 1.34 (d, J=6.80 Hz, 3H), 1.00-1.16 (m, 1H), 0.56 (td, J=8.31, 3.40 Hz, 1H), 0.42-0.50 (m, 1H), 0.26-0.41 (m, 2H).

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