Diisopropylethylamine → HCID 16041239, compound

Participants

Reaction Steps

Triphosgene (209.2, 0.47 mmol) was added to a solution of 1-(4-fluorophenyl)imidazolidin-2-one (209.2 mg, 0.71 mmol) in THF (4.7 mL) and the mixture was heated to reflux for 6 h. 1-(4-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone 270 (120.0 mg, 0.31 mmol) and DIPEA (0.1 mL, 0.5 mmol) were added and the mixture was stirred for 1 h at room temperature. The reaction mixture was transferred to a silica gel flash chromatography column and eluted with 3% MeOH in DCM affording 264 (97.6 mg, 0.16 mmol, 52% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.55 (s, 1H), 8.47 (d, 5.5 Hz, 1H), 7.84 (dd, J=2.4 Hz, 13.1 Hz, 1H), 7.71-7.63 (m, 2H), 7.54 (m, 1H), 7.48-7.42 (m, 2H), 7.31-7.27 (m, 2H), 6.63 (m, 1H), 6.42 (m, 1H), 4.21 (br, 1H), 4.15 (br, 1H), 3.96-3.93 (m, 4H), 3.71-3.65 (m, 2H), 2.70 (br, 1H), 2.59 (br, 1H), 2.09 (s, 1.5H), 2.05 (s, 1.5H). MS (m/z): (M+1) 590.2 (100%).

Provenance & Evidence