Piperidine → HCID 178428328, compound

Participants

Reaction Steps

A mixture of 2-bromo-1-(4-(5-isopropoxy-4-(4-(2-(isopropylsulfonyl)phenylamino)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylphenyl)piperidin-1-yl)ethanone from Example 8 (10 mg, 0.014 mmol), and piperidine (3 uL, 0.031 mmol) in DMF was stirred at rt overnight. The crude mixture was directly purified by reverse phase HPLC to give 1-(4-(5-isopropoxy-4-(4-(2-(isopropylsulfonyl)phenylamino)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylphenyl)piperidin-1-yl)-2-(piperidin-1-yl)ethanone. MS: m/z=703.4 (M+1), 352.2 (M/2+1). 1H-NMR (400 MHz, CD3OD): δ=8.39 (brs, 1H), 7.98 (dd, 1H, J=1.6, 8.0 Hz), 7.70 (t, 1H, J=7.6 Hz), 7.53-7.49 (m, 2H), 6.88 (s, 1H), 4.73-4.69 (m, 1H), 4.62 (sept, 1H, J=6.0 Hz), 4.31 (d, 1H, J=16.4 Hz), 4.22 (d, 1H, J=16.4 Hz), 3.85-3.82 (m, 1H), 3.60 (t, 2H, J=12.0 Hz), 3.41-3.25 (m, 2H), 3.11-3.00 (m, 3H), 2.90-2.84 (m, 1H), 2.79 (s, 3H), 2.22 (s, 3H), 1.99-1.85 (m, 7H), 1.80-1.54 (m, 3H), 1.27 (d, 6H, J=6.0 Hz), 1.24 (d, 6H, J=6.8 Hz).

Provenance & Evidence