HCID 68153991, compound → HCID 69935372, compound

Participants

Reaction Steps

2-(2-Methylphenyl)-5-(4-nitrobenzyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 755, 50 mg, 0.12 mmol) was suspended in methanol (5 mL) and the mixture was sparged under an atmosphere of nitrogen. The mixture was treated with Raney Ni (˜20 mg, spatula tip) and sparged under an atmosphere of hydrogen (1 atm). The mixture was, stirred vigorously for 6 hours at ambient temperature, sparged under an atmosphere of nitrogen, filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, CD3OD) δ 8.96 (1H, s), 8.34 (1H, d, J=6.4 Hz), 7.82 (1H, d, J=8.6 Hz), 7.67-7.58 (2H, m), 7.44-7.36 (6H, m), 7.29 (2H, d, J=8.2 Hz), 5.82 (2H, s), 2.27 (3H, s), ppm; low resolution mass spectrometry (ES+) m/z 381.0 (M+H)+; calculated for C24H20N4O: 381.2].

Provenance & Evidence