Ammonia → HCID 178513513, compound

Participants

Reaction Conditions

Reaction Steps

54 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 0.5 ml of toluene. After cooling to 0° C. using an ice bath, 90 μl of 95% sulphuric acid are added and the mixture is stirred at RT for 24 h. It is cooled to 0° C. and neutralized with 9 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 mixture (95/05 by volume). This gives 7 mg of 5-(2,6-difluorophenyl)-3-[(1-sulphamoylpiperidin-4-yl)amino]-2H-pyrazolo[4,3-c]isoquinoline-7-carboxamide (yellow solid). 1H NMR: 1.67 (m, 2 H) 2.11 (m, 2 H) 2.67 (m, 2 H) 3.47 (m, 2 H) 3.71 (m, 1 H) 6.01 (d, J=8.2 Hz, 1 H) 6.70 (broad s, 2 H) 7.33 (t, J=7.7 Hz, 2 H) 7.55 (broad s, 1 H) 7.68 (m, 1 H) 8.17 (broad s, 1 H) 8.22 (broad s, 1 H) 8.35 (broad d, J=8.5 Hz, 1 H) 8.45 (d, J=8.5 Hz, 1 H) 12.84 (s, 1 H).

Provenance & Evidence