Reaction Steps
A solution of diethyl N-(4-((1,2,5,6-tetrahydro-3-methyl-1-oxo-benzo[f]quinazolin-9-yl)sulfonamido)benzoyl)-L-glutamate (0.50 g, 0.84 mmol) in diglyme (10 ml) was stirred with 10% palladium on carbon (0.25 g) (Aldrich) under nitrogen at reflux for 3 hours. The solution was diluted with diglyme (20 ml), filtered hot through celite, and concentrated under high vacuum. The resulting solid was suspended in hot methanol (50 ml), stirred overnight at room temperature, filtered, and dried under high vacuum to give diethyl N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)sulfonamido)benzoyl)-L-glutamate as a white solid (0.25 g). 1H NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, J=7 Hz, 3H, esterCH3), 1.12 (t, J=7 Hz, 3H, esterCH3), 1.78-2.15 (m, 2H, gluCH2), 2.35 (t, J=7 Hz, 2H, gluCH2), 2.4 3 (s, 3H, C3—CH3), 3.98 (q, J=7 Hz, 2H, esterCH2), 4.04 (q, J=7 Hz, 2H, esterCH2), 2.35-4.39 (m, 1H, gluCH), 7.21 (d, J=9 Hz, 2H, Ar), 7.69 (d, J=9 Hz, 2H, Ar), 7.76 (d, J=9 Hz, 1H, Ar), 7.91 (dd, J=9, 2 Hz, 1H, Ar), 8.19 (d, J=9 Hz, 1H, Ar), 8.29 (d, J=9 Hz, 1H, Ar), 8.51 (d, J=7 Hz, 1H, gluNH), 10.44 (d, J=2 Hz, 1H, Ar), 10.88 (br s, 1H, SO2NH), 12.75 (br s, 1H, N H). Mass spectrum (CI-CH4): 595 (M+1, 24.1%). Anal. Calculated for C29H30N4O8S: C, 58.58; H, 5.08; N, 9.42; S. 5.39. Found: C, 58.46; H, 5.10; N, 9.34; S. 5.41.
