Potassium Carbonate → 4-(3-Chloro-2-fluoroanilino)-7-methoxy-6-[1-(N,N-dimethylcarbamoylmethyl)piperidin-3-yloxy]quinazoline

Participants

Reaction Steps

2-Chloro-N,N-dimethylacetamide (105 mg) was added to a mixture of 4-(3-Chloro-2-fluoroanilino)-7-methoxy-6-(piperidin-3-yloxy)quinazoline dihydrochloride (250 mg) and potassium carbonate (1.19 g) in DMF (5 ml). The mixture was stirred at room temperature for 30 mins, filtered and the solvent evaporated. Purification by flash column chromatography eluting with methylene chloride/methanol (96/4) gave a foam. This was triturated with diethyl ether and isohexane to give the title product as a white solid (105 mg); 1H NMR. Spectrum: (DMSO d6) 1.45 (m, 1H), 1.61 (m, 1H), 1.78 (m, 1H), 2.10 (m, 1H), 2.26 (m, 1H), 2.38 (m, 1H), 2.65-2.77 (m, 1H), 2.75 (s, 3H), 2.99 (s, 3H), 3.04 (m, 1H), 3.22 (s, 2H), 3.94 (s, 3H), 4.62 (m, 1H), 7.21 (s, 1H), 7.29 (m, 1H), 7.47-7.55 (m, 2H), 7.88 (s, 1H), 8.38 (s, 1H), 9.59 (s, 1H); Mass Spectrum: (M+H)+ 488.

Provenance & Evidence