Tetrahydrofuran → HCID 57737254, compound

Participants

Reaction Steps

4-[2-(3-Aminophenyl)-6-(methyloxy)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[2-(dimethylamino)ethyl]oxy}phenyl)-2-pyrimidinamine (97 mg, 0.20 mmol) and (2E)-3-phenyl-2-propenyl chloride (40 mg, 0.24 mmol) were combined in THF (2 mL) and stirred for 1 h. The mixture was diluted with DCM and TEA (2 drops), absorbed onto silica gel, and purified by silica gel chromatography to afford the title compound as a yellow solid (56 mg, 45%). 1H NMR (400 MHz, DMSO-d6) δ 10.34 (s, 1H), 9.55 (s, 1H), 8.57 (d, J=2.0 Hz, 1H), 8.45 (d, J=9.3 Hz, 1H), 8.23 (d, J=5.6 Hz, 1H), 7.97 (br s, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.62-7.59 (m, 3H), 7.55-7.53 (m, 1H), 7.47-7.39 (m, 4H), 7.30-7.26 (m, 3H), 7.14 (m, 1H), 6.81 (d, J=15.6 Hz, 1H), 6.52 (dd, J=8.2, 2.5 Hz, 1H), 6.48 (d, J=5.3 Hz, 1H), 3.99 (t, J=6.0 Hz, 3H), 3.87 (s, 3H), 2.68-2.64 (m, 2H), 2.23 (s, 6H). ES-LC/MS m/z=626 [M+H]+.

Provenance & Evidence