Potassium Carbonate → HCID 71571660, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyl-6-(3-chloropropyl)octahydropyrrolo[3,4-b][1,4]oxazine (0.30 g) in DMF (5 mL) was added K2CO3 (0.59 g), 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (0.27 g) and tetrabutylammonium iodide (20 mg). The reaction mixture was heated at 90° C. for 18 h, cooled to room temperature. The mixture was diluted with CH2Cl2 (100 mL), washed with water (100 mL×3) and brine (100 mL), and dried over anhydrous Na2SO4. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) CH2Cl2/CH3OH) to afford the title compound (390 mg, 79.59%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 579.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.07-2.09 (t, J=13.36 Hz, 2H), 2.09-2.10 (m, 1H), 2.40-2.43 (m, 1H), 2.66-2.68 (m, 2H), 2.70-2.78 (m, 2H), 3.00-3.02 (m, 1H), 3.08-3.13 (m, 1H), 3.65 (s, 3H), 3.77 (s, 1H), 3.99 (s, 3H), 4.02-4.04 (m, 1H), 4.20-4.22 (m, 2H), 5.30 (s, 1H), 7.13 (m, 1H), 7.26 (d, J=2.04 Hz, 1H), 7.30-7.31 (m, 1H), 7.56 (d, J=1.20 Hz, 5H), 7.81 (s, 1H), 7.90 (s, 1H), 7.92 (d, J=2.60 Hz, 1H), 8.64 (s, 1H) ppm.

Provenance & Evidence