4-[1-(6,7-Dimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acid tert-butyl ester → 4-[1-(6,7-Dimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of (13) (0.014 g, 0.029 mmol) in trifluoroacetic acid (3 mL) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was evaporated to a yellow solid residue (0.020 g, quantitative yield); 1H NMR (DMSO) δ 8.95 (s, 1H), 7.66 (d, 2H, J=8.7), 7.23 (s, 1H), 6.94 (s, 1H), 6.62 (d, 2H, J=8.8), 4.67 (d, 2H, J=13.6), 3.90 (s, 3H), 3.83 (s, 3H), 3.64 (m, 1H), 3.19 (t, 2H, J=11.5), 2.00 (d, 2H, J=12.8), 1.38 (m, 2H); 13C NMR (DMSO) δ 167.5, 157.9, 156.3, 151.6, 146.6, 131.2, 129.6, 123.9, 116.7, 113.8, 111.2, 105.6, 104.0, 55.9, 55.6, 48.8, 42.7, 31.2; HRMS (FAB) m/z 409.1878 (M+H)+ (C22H24N4O4 requires 409.1876); Anal. (C22H24N4O4 ·3CF3COOH·11/4H2O·1CH3OH) C, H, N.

Provenance & Evidence