Water → HCID 71285879, compound

Participants

Reaction Steps

2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-hydroxy-2,2-dimethyl-propyl)-amide (82 mg, 0.156 mmol) was suspended in dichloromethane (1.1 ml) and cooled in ice bath. Trifluoroacetic acid (0.5 ml) was added slowly and the reaction was stirred at room temperature for 3.5 h. The reaction was evaporated and the residue was dissolved in dichloromethane (1.6 ml). Ethylenediamine (0.63 ml, 9.3 mmol) was added and the mixture was stirred at room temperature for 18 h. Water and then ethyl acetate were added to the mixture, the layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (methanol/dichloromethane) to give 39 mg (63%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-hydroxy-2,2-dimethyl-propyl)-amide as an off-white solid. (M+Na)+=419; mp=291-293° C. 1H NMR (300 MHz, DMSO-d6) δ: 9.10 (s, 1H), 8.45 (s, 1H), 8.41-8.49 (m, 1H), 8.19-8.27 (m, 1H), 7.67 (dd, J=9.8, 2.3 Hz, 1H), 7.14-7.23 (m, 1H), 4.63-4.72 (m, 1H), 4.14 (s, 3H), 3.37-3.43 (m, 2H), 3.16-3.24 (m, 2H), 0.90 (s, 6H).

Provenance & Evidence