Aniline → HCID 58836884, compound

Participants

Reaction Steps

A solution of 48.5 mg (0.09 mmol) of tert-butyl 4-(2-(6-chloro-3-(2,6-dichlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)piperidine-1-carboxylate 93 in 5 mL 1,4-dioxane was treated sequentially with 17 μl (0.2 mmol) of aniline and 525 μl (7.1 mmol) of TFA. The resulting orange solution was heated at reflux for 22 h, and then was concentrated. The residue was purified by chromatography on silica gel (CH2Cl2:MeOH, 9:1) to give the title compound 94. 1H-NMR (CD3OD) δ 1.22-1.45 (m, 3H), 1.66-1.78 (m, 2H), 1.91-2.02 (m, 2H), 2.10 (s, 1H), 2.62-2.74 (m, 2H), 3.10-3.23 (m, 2H), 4.15 (t, J=6.3 Hz, 2H), 6.99 (t, J=8.0 Hz, 1H), 7.19 (t, J=8.1 Hz, 1H), 7.23-7.31 (m, 2H), 7.42 (t, J=8.5 Hz, 2H), 7.71 (d, J=8.5 Hz, 2H), 8.56 (s, 1H). Mass Spectrum (ESI) m/e=482.0 (M+1).

Provenance & Evidence