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 (61 mg, 0.12 mmol) and [(1R)-1-isocyanatoethyl]benzene (34 mg, 0.23 mmol) were combined in THF (2 mL) and stirred for 2 h, after which time additional [(1R)-1-isocyanatoethyl]benzene (10 mg, 0.068 mmol) was added in portions until the reaction was complete by LC/MS. The mixture was absorbed onto silica get and purified by silica gel chromatography to afford the title compound as a yellow solid (34 mg, 44%). 1H NMR (400 MHz, DMSO-d6) δ 9.50 (s, 1H), 8.53 (d, J=5.9 Hz, 2H), 8.45 (d, J=9.9 Hz, 1H), 8.20 (d, J=5.5 Hz, 1H), 7.64 (s, 1H), 7.51 (s, 1H), 7.44 (d, J=7.4 Hz, 1H), 7.32-7.19 (m, 7H), 7.15-7.04 (m, 3H), 6.61 (d, J=8.5 Hz, 1H), 6.51 (d, J=8.1 Hz, 1H), 6.44 (d, J=5.2 Hz, 1H), 4.78 (t, J=7.4 Hz, 1H), 3.96 (t, J=5.5 Hz, 2H), 3.85 (s, 3H), 2.56 (t, J=5.7 Hz, 2H), 2.16 (s, 6H), 1.36 (d, J=7.1 Hz, 3H). ES-LC/MS m/z 643 [M+H]+.

Provenance & Evidence