Potassium Carbonate → N-(3-chloro-4-fluorophenyl)-6-(3-(6-ethyloctahydro-1H-pyrrolo[3,4-b]pyridin-1-yl)propoxy)-7-methoxyquinazolin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine (0.80 g), K2CO3 (3.00 g) and 6-ethyloctahydro-1H-pyrrolo[3,4-b]pyridine (0.40 g) in 25 mL of DMF was stirred at 80° C. for 7 h, then cooled to rt, poured into 50 mL of ice-water and 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 give the title compound as a pale yellow solid (0.36 g, 35.00%), HPLC: 95.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 515.4 (M+1); 1H NMR (400 MHz, d6-DMSO) δ: 1.93 (t, J=4.6 Hz, 3H), 2.21-2.33 (m, 4H), 2.43-2.50 (m, 5H), 2.54-2.60 (m, 2H), 2.98-3.02 (m, 2H), 3.17-3.20 (m, 3H), 3.35-3.41 (m, 1H), 3.48-3.52 (m, 1H), 4.29 (s, 3H), 4.34 (t, J=8.6 Hz, 2H), 7.20 (s, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.43 (s, 2H), 7.91 (t, J=4.2 Hz, 1H), 8.47 (s, 1H) ppm.

Provenance & Evidence