Potassium Carbonate → HCID 86729516, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4aR,7aR)-hexahydro-2H-[1,4]dioxino[2,3-c]pyrrole (129.0 mg, 1.0 mmol), K2CO3 (217.0 mg, 1.56 mmol), tetrabutylammoniumiodide (44.0 mg, 0.12 mmol) and N-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine (475.0 mg, 1.20 mmol) in 15 mL of DMF was stirred for 9 h at 60° C., then poured into 10 mL of ice-water and extracted with CH2Cl2. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) DCM/MeOH) to give the title compound as a pale yellow solid (120 mg, 24.50%), HPLC: 94.43%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 489.9 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.04 (m, 2H), 2.6 (br, 1H), 2.72 (m, 2H), 2.82 (m, 2H), 3.04 (m, 2H), 3.64 (t, J=6.08 Hz, 2H), 3.80 (m, 4H), 3.98 (s, 3H), 4.16 (t, J=6.48 Hz, 2H), 7.14 (t, J=8.76 Hz, 1H), 7.23 (d, J=7.8 Hz, 1H), 7.58 (m, 2H), 7.90 (dd, J1=6.48 Hz, J2=2.56 Hz, 1H), 8.65 (s, 1H).

Provenance & Evidence