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-(methyloxy)-5-[3-(2-{[2-(trifluoroacetyl)-1,2,3,4-tetrahydro-7-isoquinolinyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}benzamide (50 mg, 0.072 mmol) in 10:1 THF:H2O (10 mL) was added 1M LiOH (0.43 ml, 0.43 mmol) and the reaction mixture was heated at 50° C. overnight. The reaction was washed with brine (10 mL), organic layer removed, adsorbed to silica gel and purified by column chromatography (0-10% MeOH/DCM+1% NH4OH) to afford the title compound (32 mg, 74%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 2.75 (t, 2H, J=5.86 Hz), 3.13 (t, 2H, J=5.86 Hz), 3.93 (s, 3H), 3.97 (s, 2H), 6.64 (d, 1H, J=5.31 Hz), 6.86-6.89 (m, 1H), 6.94-7.03 (m, 4H), 7.24-7.44 (m, 5H), 8.16 (d, 1H, J=5.31 Hz), 8.32-8.38 (m, 2H), 8.50 (d, 1H, J=6.96 Hz), 8.98 (m, 1H); ESIMS (M+H)+=604.

Provenance & Evidence