Trifluoroacetic acid → HCID 71288434, compound

Participants

Reaction Steps

To a stirred solution of N-(1-hydroxy-2-methylpropan-2-yl)-2-(3-(1-methylpiperidin-4-yl)-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (57 m g, 98.7 μmol) in dichloromethane (3 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 added. After 1 h the mixture was concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-6% methanol containing 10% ammonium hydroxide in dichloromethane) gave 2-[3-(1-methyl-piperidin-4-yl)indazol-1-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)amide (10 mg, 23%). MS (M+H)+=447; 1H NMR (DMSO-d6) δ: 9.00 (s, 1H), 8.64 (d, J=8.5 Hz, 1H), 8.37 (s, 1H), 7.99 (d, J=7.9 Hz, 1H), 7.65 (s, 1H), 7.57 (t, J=7.3 Hz, 1H), 7.35 (t, J=7.5 Hz, 1H), 5.06 (t, J=5.7 Hz, 2H), 3.62 (d, J=5.7 Hz, 2H), 2.98 (d, J=11.5 Hz, 2H), 2.30 (s, 3H), 1.94-2.24 (m, 5H), 1.44 (s, 6H)

Provenance & Evidence