Potassium Carbonate → HCID 71572332, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (0.50 g, 0.16 mmol, 1.0 eq) and K2CO3 (0.05 g, 0.32 mmol, 2.0 eq) in 20 mL of DMF was added 5-(3-chloropropyl)-1,3-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (0.05 g, 0.19 mmol, 1.2 eq) at room temperature. The reaction mixture was heated at 80° C. for 8.0 h and concentrated in vacuo. The residue was poured into a mixture of water (100 mL) and CH2Cl2 (150 mL). 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 yellow solid (0.20 g, 24.98%), HPLC: 95.21%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 513.02 (M+1); 1H NMR (400 MHz, d6-DMSO) δ: 1.91-2.08 (m, J=4.0 Hz 2H), 2.51 (s, 3H), 2.78 (s, 3H), 2.79-2.89 (m, 6H), 2.90-2.96 (m, 2H), 3.95 (s, 3H), 4.19 (m, 2H), 7.25 (s, 1H), 7.47 (t, J=8.12 Hz, 1H), 7.54 (s, 2H), 8.11 (t, J=5.16 Hz, 1H), 8.50 (s, 1H) ppm.

Provenance & Evidence