5-tert-Butyl-2-(2-(hydroxymethyl)-3-(1-methyl-5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)isoindolin-1-one → 5-(Dimethylamino)-2-(2-(hydroxymethyl)-3-(1-methyl-5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)isoindolin-1-one

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Reaction Steps

Using the same general procedure as described for the preparation of 103 reaction of 123e (450 mg, 1.00 mmol) with 103l (260 mg, 0.800 mmol) followed by a hydrolysis gave a 24% yield (130 mg) of 123 as a white solid: mp 148-150° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.09 (s, 1H), 7.98 (d, 1H, J=2.0 Hz), 7.56 (d, 1H, J=8.0 Hz), 7.47 (t, 1H, J=8.0 Hz), 7.39 (dd, 1H, J=8.0, 1.5 Hz), 7.33 (dd, 1H, J=8.0, 1.5 Hz), 7.24 (d, 1H, J=2.0 Hz), 6.88-6.85 (m, 2H), 5.88 (s, 1H), 4.89 (t, 1H, J=5.0 Hz), 4.85 (s, 2H), 4.31 (d, 2H, J=5.0 Hz), 3.91 (t, 2H, J=5.5 Hz), 3.59 (s, 3H), 3.48 (s, 2H), 3.04 (s, 6H), 2.77 (t, 2H, J=5.5 Hz), 2.34 (s, 3H); MS (ESI+) m/z 540.3 (M+H).

Provenance & Evidence