Lithium Hydroxide → 2,6-Difluoro-N-(2-(methyloxy)-5-{3-[2-(1,2,3,4-tetrahydro-7-isoquinolinylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-difluoro-N-{2-fluoro-5-[3-(2-{[2-(trifluoroacetyl)-1,2,3,4-tetrahydro-7-isoquinolinyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}benzamide (55 mg, 0.08 mmol) in 10:1 THF:H2O (10 mL) was added 1M LiOH (0.48 mL, 0.48 mmol) and the reaction mixture was heated at 50° C. overnight. The reaction was washed with brine (10 mL) and the organic layer removed, adsorbed to silica gel and purified by column chromatography (0-10% MeOH/DCM+1% NH4OH) to afford the title compound (39 mg, 82%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.72 (t, 2H, J=5.86 Hz), 3.04 (t, 2H, J=5.86 Hz), 3.86 (s, 2H), 6.55 (d, 1H, J=5.30 Hz), 6.88-6.97 (m, 4H), 7.11-7.16 (m, 1H), 7.23-7.39 (m, 5H), 8.09 (t, 1H, J=5.31 Hz), 8.28-8.29 (d, 1H, J=8.78 Hz), 8.45 (d, 1H, J=6.95 Hz), 8.61-8.63 (m, 1H); ESIMS (M+H)+=592.

Provenance & Evidence