Trifluoroacetic acid → HCID 71279740, compound

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Reaction Steps

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-(N-methylacetamido)propyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (72 mg, 112 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 was added. After 1 h the mixture was concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0 to 5% methanol containing 10% ammonium hydroxide in dichloromethane) gave 2-{1-[3-(acetyl-methyl-amino)-propyl]-5-difluoromethoxy-1H-indazol-3-yl}-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (32 mg, 56%). MS (M+H)+=514; 1H NMR (DMSO-d6) δ: 9.09 (s, 1H), 8.39 (s, 1H), 8.22 (br. s., 1H), 7.84-7.98 (m, 2H), 7.40 (d, J=9.8 Hz, 1H), 6.93-7.47 (m, 1H), 4.48-4.60 (m, 1H), 3.36-3.42 (m, 2H), 2.95 (s, 3H), 2.79 (s, 3H), 1.93 (d, J=7.5 Hz, 2H), 1.51 (s, 9H).

Provenance & Evidence