5-tert-Butyl-2-(3-(5-(1,5-dimethyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(hydroxymethyl)phenyl)isoindolin-1-one → 5-tert-Butyl-2-(2-(hydroxymethyl)-3-(1-methyl-6-oxo-5-(pyridin-2-ylamino)-1,6-dihydropyridin-3-yl)phenyl)isoindolin-1-one

Participants

Role	Name	HCID	Charge
Reactant	5-tert-Butyl-2-(3-(5-(1,5-dimethyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(hydroxymethyl)phenyl)isoindolin-1-one	HCID 56928443	—
Reactant	5-Bromo-1-methyl-3-(pyridin-2-ylamino)-1h-pyridin-2-one	HCID 66598773	—
Reactant	2-(5-tert-Butyl-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate	HCID 86697936	—
Product	5-tert-Butyl-2-(2-(hydroxymethyl)-3-(1-methyl-6-oxo-5-(pyridin-2-ylamino)-1,6-dihydropyridin-3-yl)phenyl)isoindolin-1-one	HCID 56928552	34%

Reaction Steps

Using the same general procedure as described for the preparation of 105, reaction 103f (298 mg, 0.643 mmol) with 113a (150 mg, 0.536 mmol) gave a 34% yield (90 mg) of 113 as a white solid: mp 138-139° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.68 (d, 1H, J=2.0 Hz), 8.58 (s, 1H), 8.17 (m, 1H), 7.73-7.71 (m, 2H), 7.62-7.56 (m, 2H), 7.50 (t, 1H, J=7.5 Hz), 7.44 (d, 1H, J=7.5 Hz), 7.39-7.37 (m, 2H), 7.28 (d, 1H, J=7.5 Hz), 6.78 (dd, 1H, J=6.5, 5.0 Hz), 4.94 (s, 2H), 4.89 (t, 1H, J=4.5 Hz), 4.34 (d, 2H, J=4.5 Hz), 3.60 (s, 3H), 1.65 (s, 9H); MS (ESI+) m/z 495.2 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249123B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-41f5a2facb9743bbacfefa9307a069a1
Source note	uspto-grants-2016_02