Potassium Hydroxide → HCID 178493016, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-({2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-2,3-dihydro-1H-isoindol-1-one (140 mg, 0.210 mmol) in 1,4-dioxane (8 mL) was added 1.0M potassium hydroxide (6.30 mL, 6.30 mmol) and the resulting reaction was heated in a microwave reactor at 120° C. for 20 min. The reaction was washed with brine (5 ml), organic layer diluted with ethyl acetate (10 mL), adsorded onto silica gel and purified by silica gel chromatography (DCM to 10% MeOH/DCM) to produce 7-[(2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2,3-dihydro-1H-isoindol-1-one (0.070 g, 75%). ESIMS (M+H)+=513. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02 (d, J=6.42 Hz, 6 H) 2.61 (d, J=9.23 Hz, 4 H) 3.08-3.16 (m, 4 H) 3.81 (s, 3 H) 4.39 (s, 2 H) 6.27 (dd, J=3.41, 1.81 Hz, 1 H) 6.51 (dd, J=8.73, 2.51 Hz, 1 H) 6.64 (d, J=2.61 Hz, 1 H) 6.97 (dd, J=3.41, 2.21 Hz, 1 H) 7.10 (d, J=7.62 Hz, 1 H) 7.43-7.50 (m, 1 H) 7.53 (s, 1 H) 7.83 (d, J=8.83 Hz, 1 H) 8.69 (d, J=8.23 Hz, 2 H) 8.79 (s, 1 H) 10.45 (s, 1 H) 11.33 (s, 1 H).

Provenance & Evidence