Phosgene → HCID 59239532, compound

Participants

Reaction Conditions

Reaction Steps

Step 3—Synthesis of compound ux: (S)-1-(2-(4-aminophenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethanone (0.100 g, 0.000272 mol) in dry 1,4-Dioxane (2.00 mL, 0.0256 mol) was added Triethylamine (0.0416 mL, 0.000299 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.160 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added 2,2,2-trifluoroethylamine (0.1280 mL, 0.001627 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 9.01 (d, J=5.1, 1H), 8.21 (dd, J=8.8, 2.7, 2H), 7.52 (d, J=8.4, 2H), 6.82 (t, J=6.4, 1H), 4.74-4.43 (m, 2H), 4.16 (s, 1H), 4.00-3.85 (m, 3H), 3.64 (ddd, J=19.4, 16.7, 9.4, 6H), 3.43 (d, J=21.0, 2H), 2.76 (s, 1H), 2.63 (s, 1H), 2.12 (s, 3H), 1.33-1.22 (m, 3H). LC/MS-m/z+493.2 (M+H)+

Provenance & Evidence