Water → 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (S)-N-(tetrahydro-pyran-3-yl)-amide

Participants

Reaction Steps

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (S)—N-(tetrahydro-pyran-3-yl)-amide (55 mg, 0.10 mmol) was dissolved in dichloromethane (1.2 ml) and cooled in ice bath. Trifluoroacetic acid (0.6 ml) was slowly added and the reaction was stirred at room temperature for 3 h. The reaction was evaporated and the residue was dissolved in dichloromethane (1 ml). Ethylenediamine (0.41 ml, 6.1 mmol) was added and the mixture was stirred for 18 h. Water and then ethyl acetate were added to the mixture. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with sodium chloride solution, dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography (methanol/dichloromethane) to give 30 mg (71%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (S)—N-(tetrahydro-pyran-3-yl)-amide. MS: (M+H)+=411; mp=320-323° C. 1H NMR (300 MHz, DMSO-d6) δ: 9.10 (s, 1H), 8.50 (d, J=8.7 Hz, 1H), 8.44 (s, 1H), 8.16 (d, J=7.6 Hz, 1H), 7.96 (d, J=1.9 Hz, 1H), 7.24 (dd, J=8.5, 1.7 Hz, 1H), 4.16 (s, 3H), 4.04-4.14 (m, 1H), 3.86-3.94 (m, 1H), 3.62-3.73 (m, 2H), 3.46-3.55 (m, 1H), 1.93-2.08 (m, 1H), 1.69-1.89 (m, 2H), 1.50-1.68 (m, 1H).

Provenance & Evidence