Ammonia → HCID 49764525, compound

Participants

Reaction Conditions

Reaction Steps

116 mg of 5-(2,6-difluorophenyl)-N-[1-(methylsulphonyl)piperidin-4-yl]-7-(2H-1,2,3-triazol-4-yl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-pyrazolo[4,3-c]isoquinolin-3-amine are introduced into 10 ml of DCM. After cooling to 0° C. using an ice bath, 1.1 ml of TFA are added and the mixture is stirred at RT for 5 h. It is concentrated under RP and the solid obtained is taken up in 60 ml of water, neutralized with 7.5M aqueous ammonia solution. It is extracted with ethyl acetate, dried over MgSO4, filtered and concentrated under RP. The product is purified by flash chromatography on silica gel (15-40 μm), eluting with a DCM/methanol mixture (92.5/7.5 by vol.), to give 10 mg of 5-(2,6-difluorophenyl)-N-[1-(methylsulphonyl)piperidin-4-yl]-7-(2H-1,2,3-triazol-4-yl)-1H-pyrazolo[4,3-c]isoquinolin-3-amine (yellow solid). 1H NMR: 1.62-1.75 (m, 2 H) 2.10 (m, 2 H) 2.82-2.97 (m, 5 H) 3.57 (m, 2 H) 3.74-3.86 (m, 1 H) 6.04 (d, J=8.0 Hz, 1 H) 7.35 (t, J=8.0 Hz, 2 H) 7.63-7.75 (m, 1H) 8.13 (broad s, 1 H) 8.39 (broad d, J=8.6 Hz, 1 H) 8.45 (broad m, 1 H) 8.49 (d, J=8.6 Hz, 1 H) 12.77 (s, 1 H) 15.23 (broad m, 1 H).

Provenance & Evidence