Potassium Carbonate → HCID 71572792, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(3-chloropropyl)octahydro-2H-pyrano[3,2-b]pyridine (0.23 g), K2CO3 (0.26 g) and 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (0.30 g) in 20 mL of DMF was stirred at 80° C. for 7 h and cooled to rt. To this, 50 mL of ice-water was added and the mixture was extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column eluting agent: 20:1 (v/v) DCM/MeOH) to afford the title compound as a pale yellow solid (0.11 g, 25.00%), HPLC: 96.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 501.3 (M+1); 1H NMR (400 MHz, d6-DMSO) δ: 9.54 (s, 1H), 7.78 (d, J=4.0 Hz, 1H), 7.70 (t, J=8.0 Hz, 1H), 7.64 (s, 2H), 7.24 (d, J=4.2 Hz, 1H), 7.09 (t, J=8.0 Hz, 1H), 4.19 (m, 2H), 3.93 (s, 3H), 3.33-3.30 (m, 2H), 2.51-2.49 (m, 4H), 2.14-1.93 (m, 6H), 1.74-1.71 (m, 3H), 1.36-1.23 (m, 3H) ppm.

Provenance & Evidence