Isovaleryl chloride → HCID 52913022, compound

Participants

Reaction Steps

2-(2-Aminophenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 626, 30 mg, 0.069 mmol) and diisopropylethylamine (30 μL, 0.17 mmol, 2.5 equiv) were combined in dichloromethane (1 mL) and treated with 3-methylbutanoyl chloride (9.2 mg, 0.076 mmol, 1.1 equiv). After 15 minutes at ambient temperature, the mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (eluting 80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the title compound; 1H-NMR (400 MHz, d6-DMSO) δ 9.72 (1H, br s), 9.33 (1H, s), 8.47 (1H, d, J=2.3 Hz), 8.28 (1H, d, J=7.7 Hz), 7.93 (1H, d, 8.0 Hz), 7.84 (1H, d, J=8.9 Hz), 7.83 (2H, d, J=8.5 Hz), 7.72 (1H, br s), 7.69-7.64 (2H, m), 7.59 (1H, t, J=7.3 Hz), 7.47 (2H, d, J=8.4 Hz), 7.37 (1H, t, J=7.5 Hz), 7.27 (1H, t, J=7.5 Hz), 6.53 (1H, m), 5.83 (2H, s), 2.15 (2H, d, J=7.3 Hz), 2.09-1.94 (1H, m), 0.86 (6H, d, J=6.6 Hz) ppm; high resolution mass spectrometry (ES+) m/z 517.2391 [(M+H)+; calculated for C31H29N6O2: 517.2347].

Provenance & Evidence