Methylamine → 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide

Participants

Role	Name	HCID	Charge
Reactant	Methylamine	HCID 6329	—
Reactant	Methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate	HCID 67114669	—
Solvent	Methanol	HCID 887	—
Product	2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide	HCID 67114970	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

Methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate (Intermediate 27A) (0.1 g, 0.46 mmol) and 2M methylamine in methanol (5 mL) were sealed in a tube and heated at 90° C. overnight. The reaction mixture was concentrated and purified by a 10 g silica column eluting with 0-10% methanol in DCM to afford 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide (96 mg, 0.31 mmol).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841289B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-3e59eb3b3eb9406283bfe5156658b028
Source note	uspto-grants-2014_09