Morpholine → 5-Methyl-7-morpholin-4-yl-2-(2-[1,2,4]triazolo[1,5-a]pyridin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

Participants

Role	Name	HCID	Charge
Reactant	Morpholine	HCID 8083	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	2-(2-([1,2,4]Triazolo[1,5-A]pyridin-2-YL)ethyl)-7-chloro-5-methyl-2,3-dihydro-1H-pyrrolo[3,4-C]pyridine-1,6(5H)-dione	HCID 73424721	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-Methyl-7-morpholin-4-yl-2-(2-[1,2,4]triazolo[1,5-a]pyridin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione	HCID 86296275	14.82%

Reaction Conditions

Temperature	120 °C

Reaction Steps

Palladium diacetate (65.3 mg, 0.291 mmol), Xantphos (168 mg, 0.291 mmol) and Cs2CO3 (284 mg, 0.873 mmol) were each rapidly added in sequence to a suspension of 7-chloro-5-methyl-2-(2-[1,2,4]triazolo[1,5-a]pyridin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (100 mg, 0.291 mmol, see Example c6)) and morpholine (25.3 mg, 0.291 mmol) in dioxane (5 ml). The reaction mixture was heated in a microwave at about 120° C. for about 40 min. The solvent was removed and the resulting mixture was purified by preparative HPLC (system: Waters 2767 PHW003, eluent: MeCN/ammonium acetate buffer (gradient: 7:93 to 30:70 over 15 min), column: Boston Analytics, C-18, 10 μm, 10×250 mm) to afford the title compound (17 mg, 0.043 mmol, 14.82% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09163019B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-2f7af32a9a084663bf0985f7d0dc1e35
Source note	uspto-grants-2015_10