Diisopropylethylamine → N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-oxo-3-(piperidin-1-yl)imidazolidine-1-carboxamide

Participants

Reaction Steps

Triphosgene (107 mg, 0.36 mmol) was added to a solution of 1-(piperidin-1-yl)imidazolidin-2-one (278) (120 mg, 0.71 mmol) in THF (7.1 mL) and the mixture was refluxed 6 h the solution was cooled down. 3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline (12) (150.0 mg, 0.44 mmol) and DIPEA (0.186 mL, 1.07 mmol) were added and the mixture stirred 1 h at room temperature. The reaction mixture was filtered, the solution transferred to a flash chromatography column and eluted with 2% to 5% MeOH in DCM affording title compound 276 (176.4 mg, 0.33 mmol, 75% yield) as a creamy solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.57 (s, 1H), 8.4 (d, J=5.4 Hz, 1H), 7.86 (s, 1H), 7.79 (dd, J=2 Hz, J=12.9 Hz, 1H), 7.72 (s, 1H), 7.68 (s, 1H), 7.46 (t, J=8.9 Hz, 1H), 7.36 (m, 1H), 6.58 (d, 5.4 Hz, 1H), 3.76 (dd, J=7.7 Hz, J=8.2 Hz, 2H), 3.73 (s, 3H), 3.54 (dd, J=8.2 Hz, J=7.7 Hz, 2H), 2.9-2.87 (m, 4H), 1.59 (m, 4H), 1.35 (m, 2H). MS (m/z): (M+1) 536.2 (100%)

Provenance & Evidence