Dichloromethane → HCID 71572791, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(3-chloropropyl)octahydro-[1,4]dioxino[2,3-c]pyridine (100 mg, 0.46 mmol, 1 eq), 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (145 mg, 0.46 mmol, 1 eq) and K2CO3 (128 mg, 0.92 mmol, 2 eq) in DMF (10 mL) was heated at 80° C. overnight under N2, and cooled to room temperature. To this, 100 mL of CH2Cl2 was added. The mixture was washed with brine (20 mL×3) and water (20 mL×2). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (20:1 (v/v) CH2Cl2/MeOH) to afford the title compound as a yellow solid (60 mg, 28.00%), HPLC: 95.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 503.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.04-2.10 (2H, m), 2.21-2.48 (3H, m), 2.60-2.63 (2H, m), 2.92-3.08 (2H, m), 3.56-3.62 (2H, m), 3.67-3.72 (1H, m), 3.76-3.82 (2H, m), 3.52-3.53 (1H, m), 3.97 (2H, s), 4.08-4.15 (2H, m), 7.10-7.15 (1H, m), 7.21 (1H, s), 7.31 (1H, s), 7.62-7.65 (1H, m), 7.93-7.94 (1H, m), 8.62 (1H, s) ppm.

Provenance & Evidence