Hydrochloric Acid → 5-(2,6-difluorophenyl)-3-{[1-(ethylsulphonyl)piperidin-4-yl]amino}-1H-pyrazolo[4,3-c]isoquinoline-7-carbaldehyde oxime

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Reaction Steps

A 25 ml round-bottomed flask is charged with 30 mg of 5-(2,6-difluorophenyl)-3-{[1-(ethylsulphonyl)piperidin-4-yl]amino}-1H-pyrazolo[4,3-c]isoquinoline-7-carbaldehyde, prepared in example 19, in 2 ml of pyridine. 7 mg of hydroxylamine as the hydrochloride are added. After 1 h at RT, the mixture is evaporated under RP. The product is purified by flash chromatography on silica gel (15-40 μm), eluting with a DCM/methanol mixture (95/5 by vol.), to give 22 mg of 5-(2,6-difluorophenyl)-3-{[1-(ethylsulphonyl)piperidin-4-yl]amino}-1H-pyrazolo[4,3-c]isoquinoline-7-carbaldehyde oxime (yellow solid). 1H NMR (500 MHz, DMSO-d6) δ ppm with the E or Z isomerism: 1.23 (t, J=7.4 Hz, 3 H) 1.63 (m, 2 H) 2.09 (m, 2 H) 2.97 (m, 2 H) 3.05 (q, J=7.4 Hz, 2 H) 3.61 (m, 2 H) 3.80 (m, 1 H) 6.08 (broad m, 1 H) 7.33 (m, 2 H) 7.66 (m, 1 H) 7.86 (broad s, 1 H) 8.14 (broad d, J=8.3 Hz, 1 H) 8.30 (5, 1 H) 8.41 (d, J=8.3 Hz, 1 H) 11.45 (broad m, 1 H) 12.82 (broad m, 1 H). [M+H]+m/z=515.

Provenance & Evidence