Potassium Carbonate → HCID 71572225, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (1.20 g), K2CO3 (2.60 g) and 5-(3-chloropropyl)-3-methyl-4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine (0.97 g) in 10 mL of DMF was stirred at 80° C. for 7 h, and treated with 250 mL of ice-water. Then the mixture was extracted with CH2Cl2 (50 mL×2). The combined organic phases were dried over 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 give the title compound as a pale yellow solid (0.80 g, 45.00%), HPLC: 95.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 498.1 (M+1); 1H NMR (400 MHz, d6-DMSO) δ: 2.08 (m, J=4.0 Hz 2H), 2.51 (s, 3H), 2.70 (m, J=4.0 Hz, 6H), 2.37 (m, J=4.0 Hz, 2H), 3.94 (s, 3H), 4.20 (m, J=8.0 Hz, 2H), 7.21 (s, 1H), 7.42 (t, J=8.0 Hz, 1H), 7.44 (s, 2H), 8.11 (t, J=4.0 Hz, 1H), 8.50 (s, 1H) ppm.

Provenance & Evidence