Toluene → 3-[5-amino-4-(3-formylbenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

Participants

Reaction Steps

A mixture of 3-[5-amino-4-(3-[1,3]dioxolan-2-yl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide 5 (Example 8, 1.14 g, 2.6 mmol) was suspended in aqueous AcOH (10 mL, 1.5 M in H2O). Glacial AcOH was added dropwise until a clear solution was obtained. The reaction mixture was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure to give a residue. Toluene and EtOAc were added and the mixture was concentrated again to give the crude product that could be purified by silica gel chromatography (hexanes/EtOAc: 1/4). The desired 3-[5-amino-4-(3-formyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide 6 was obtained as a yellow foamy solid (0.91 g, 89%). MS m/z 389.1 [M+H]+; 1H NMR (300 MHz, CDCl3) 0.61 (m, 2H), 0.85 (dd, J1=6.9 Hz, J2=12.4 Hz, 2H), 2.25 (s, 3H), 2.87 (m, 1H), 5.95 (brs, 2H), 6.57 (brs, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.67-7.78 (m, 4H), 8.07 (s, 1H), 8.09 (d, J=1.3 Hz, 1H), 8.31 (s, 1H), 10.12 (s, 1H) ppm.

Provenance & Evidence