5-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one → 5-tert-Butyl-2-(3-(6-(1-cyclopropyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-(hydroxymethyl)phenyl)isoindolin-1-one

Participants

Role	Name	HCID	Charge
Reactant	5-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one	HCID 58044218	—
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-(3-(6-(1-cyclopropyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-(hydroxymethyl)phenyl)isoindolin-1-one	HCID 86699862	35.1%

Reaction Steps

Using the same general procedure as Example 105, reaction of 109c (310 mg, 1.00 mmol) and 103f (536 mg, 1.20 mmol) afforded a 35% yield (184 mg) of 109 as an off-white solid: mp 218-219° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.58 (s, 1H), 8.20 (s, 1H), 7.73 (m, 3H), 7.61 (m, 2H), 7.51 (t, 1H, J=7.9 Hz), 7.43 (m, 1H), 7.31 (s, 1H), 4.95 (s, 2H), 4.90 (t, 1H, J=5.0 Hz), 4.48 (d, 2H, J=5.0 Hz), 3.64 (m, 1H), 3.52 (s, 3H), 1.37 (s, 9H), 0.93 (m, 4H); MS (ESI+) m/z 525.2 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249123B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-f9eafbfaa8544883acc5dd891ac6bf4f
Source note	uspto-grants-2016_02