Hydrazine hydrate (1:1) → HCID 10006598, compound

Participants

Reaction Steps

To N-{1-[(R)-1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-ylmethyl}-phthalimide (3.50 g, 5.5 mMol) in EtOH (100 mL) was added hydrazine monohydrate (1.1 mL, 22.7 mMol). The reaction was stirred at RT for 72 h, filtered through a pad of Celite® to remove the insoluble precipitate, rinsed with EtOH and evaporated to dryness. Purification by flash chromatography on silica gel [5–10% (5% NH4OH in MeOH)/CH2Cl2] gave the title compound (2.71 g, 96%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.24 (d, J=8.6 Hz, 1H), 7.80 (d, J=2.0 Hz, 1H), 7.40–7.51 (m, 6H), 7.15–7.22 (m, 3H), 6.43 (d, J=7.1 Hz, 2H), 5.78 (d, J=16.3 Hz, 1H), 4.84 (d, J=10.5 Hz, 1H), 3.87 (d, J=16.3 Hz, 1H), 3.83 (2d, 2H), 3.00 (m, 1H), 2.60 (br s, 2H), 2.54 (s, 3H), 0.90 (d, J=6.7 Hz, 3H), 0.31 (d, J=6.7 Hz, 3H); MS (ES) m/e 512.2 (M+H)+.

Provenance & Evidence