Ammonia → HCID 49764647, compound

Participants

Reaction Conditions

Reaction Steps

306 mg of 4-{[7-cyano-5-(2,6-difluorophenyl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-pyrazolo[4,3-c]isoquinolin-3-yl]amino}piperidine-1-sulphonamide are introduced into 20 ml of DCM. After cooling to 0° C. using an ice bath, 1.5 ml of TFA are added and the mixture is stirred at RT for 16 h. It is concentrated under RP and the solid obtained is taken up in 30 ml of water, neutralized with 2 ml of 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/NH4OH mixture (92.5/7.5/0.75 by volume). This gives 8 mg of 4-{[7-cyano-5-(2,6-difluorophenyl)-1H-pyrazolo[4,3-c]isoquinolin-3-yl]amino}piperidine-1-sulphonamide. 1H NMR: 1.61-1.73 (m, 2 H) 2.09 (m, 2 H) 2.63-2.72 (m, 2 H) 3.47 (m, 2 H) 3.67-3.76 (m, 1 H) 6.13 (d, J=7.0 Hz, 1 H) 6.70 (s, 2 H) 7.34 (t, J=7.8 Hz, 2 H) 7.65-7.74 (m, 1 H) 8.18 (broad s, 1 H) 8.28 (broad d, J=8.6 Hz, 1 H) 8.56 (d, J=8.6 Hz, 1 H) 13.05 (s, 1 H).

Provenance & Evidence