Ethyl Acetate → (3-Methoxy-4-phenoxy-phenyl)-(6-piperidin-4-ylethynyl-quinazolin-4-yl)-amine

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Reaction Steps

A solution of 4-(4-chloro-quinazolin-6-ylethynyl)-piperidine-1-carboxylic acid tert-butyl ester (131 mg, 0.304 mmol) and 3-methoxy-4-phenoxyaniline hydrochloride (77 mg, 0.306 mmol) in tBuOH/ClCH2CH2Cl (1.0 /1.0 mL) was heated in a tightly capped reaction vial at 90° C. for 30 minutes. After cooling, the yellow mixture was diluted with MeOH and HCl gas was passed through the mixture for 10 minutes. After stirring for 2 hours, EtOAc was added to precipitate more solid which was collected by suction filtration, rinsed with EtOAc, and further dried to give 105 mg (66%) of yellow solid: 1H NMR (CD3OD) δ 1.93 -2.02 (m, 2H), 2.18 -2.24 (m, 2H), 3.12 -3.21 (m, 2H), 3.41 -3.47 (m, 2H), 3.81 (s, 3H), 6.87 (d, 2H), 7.02 (t, 1H), 7.06 (d, 1H), 7.27 (t, 2H), 7.33 (dd, 1H), 7.56 (d, 1H), 7.80 (d, 1H), 8.06 (d, 1H), 8.79 (s, 1H), 8.83 (s, 1H); MS m/z (MH+) 451.3.

Provenance & Evidence