Trifluoroacetic acid → HCID 49764270, compound

Participants

Reaction Conditions

Reaction Steps

A 10 ml round-bottomed flask equipped with a magnetic stirrer is charged with 50 mg of 5-(2,6-difluorophenyl)-3-{[1-(ethylsulphonyl)piperidin-4-yl]amino}-1-([2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazolo[4,3-c]isoquinoline-7-carbonitrile in 5 ml of DCM. After cooling to 0° C. using an ice bath, 0.1 ml of TFA is added and the mixture is stirred at RT for 3 h. It is concentrated under RP and the solid obtained is taken up in 20 ml of water and extracted with three times 20 ml of AcOEt. The combined organic phases are dried over MgSO4, filtered and concentrated under RP. The product is purified by flash chromatography on silica gel (15-40 μm), eluting with DCM and with a mixture of DCM and methanol (90/10 by vol.), to give 27 mg of 5-(2,6-difluorophenyl)-3-{[1-(ethylsulphonyl)piperidin-4-yl]amino}-1H-pyrazolo[4,3-c]isoquinoline-7-carbonitrile (yellow solid). 1H NMR (400 MHz, DMSO-d6) 1.23 (t, J=7.3 Hz, 3 H) 1.63 (m, 2 H) 2.09 (m, 2 H) 2.97 (m, 2 H) 3.05 (q, J=7.3 Hz, 2 H) 3.61 (m, 2 H) 3.81 (m, 1 H) 6.23 (broad m, 1 H) 7.34 (t, J=7.8 Hz, 2 H) 7.70 (m, 1 H) 8.18 (broad s, 1 H) 8.27 (broad d, J=8.5 Hz, 1 H) 8.56 (d, J=8.5 Hz, 1 H) 13.07 (broad s, 1 H) LC-MS-DAD-ELSD: 497 (+)=(M+H)(+).

Provenance & Evidence