HCID 86659827, compound → HCID 46840314, compound

Participants

Reaction Steps

A solution of (E)-3-(4-sec-butylphenyl)-2-(4-(2-(dimethylamino)vinyl)-3-nitrophenyl)quinazolin-4(3H)-one (0.565 g, 1.20 mmol) in a 3:1 mixture of EtOH/DMF (25 mL) was flushed with N2. Pd/C (0.060 g, 10 wt %) was added and flushed with H2 for 2.5 hours. After filtering through diatomaceous earth, the filtrate was concentrated. Purification was effected by flash chromatography on silica gel, eluting with 5% to 75% EtOAc in heptane, Further purification was effected by reverse-phase chromatography, eluting with 10% to 90% CH3CN in H2O with 0.1% TFA. The desired fractions were collected, basified, and extracted with CH2Cl2, to afford the title compound as a white solid (0.040 g, 8%). 1H-NMR (300 MHz, DMSO-d6): δ11.27 (s, 1H), 8.18 (d, J=8.0 Hz, 1H), 7.87-7.90 (m 1H), 7.75 (d, J=7.8 Hz, 1H), 7.56-7.59 (m, 1H), 7.50 (s, 1H), 7.37 (d, J=2.6 Hz, 1H), 7.27 (d, J=8.3 Hz, 1H), 7.19-7.22 (m, 2H), 7.08-7.10 (m, 2H), 6.89-6.92 (m, 1H), 6.34 (s, 1H), 2.51-2.61 (m, 1H), 1.33-1.20 (m, 2H), 1.11 (d, J=6.9 Hz, 3H), 0.59 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 394 (M+H)+.

Provenance & Evidence