Water → 2-(6-chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide

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Reaction Steps

2-(6-Chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide (46 mg, 0.09 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 2 h. The reaction was evaporated and the residue was dissolved in dichloromethane (1 ml). Ethylenediamine (0.36 ml, 5.3 mmol) was added and the mixture was stirred for 18 h. Water and then ethyl acetate were added to the mixture. The resulting precipitate was filtered off, rinsed with water diethyl ether and ethyl acetate and set aside. The organic filtrate was separated, washed with sodium chloride solution and dried over sodium sulfate. After evaporation, the residue was combined with the precipitate collected above. The solids were dried under high vacuum to afford 34 mg (98%) of 2-(6-chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide. MS: (M+H)+=387; mp=347-349° C. 1H NMR (300 MHz, DMSO-d6) δ: 9.01 (s, 1H), 8.42 (s, 1H), 8.22-8.33 (m, 1H), 7.88 (s, 1H), 7.20-7.32 (m, 1H), 4.13-4.30 (m, 1H), 4.18 (s, 3H), 1.24 (d, J=6.4 Hz, 6H).

Provenance & Evidence