Sodium Hydroxide → 2-[4-(4-Methylhexahydro-1,4-diazepin-1-yl)-benzylamino]-N-(5-chloropyridin-2-yl)pyridine-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	2-Chloro-N-(5-chloro-2-pyridinyl)-3-pyridinecarboxamide	HCID 3421109	—
Reactant	4-(4-Methyl-1,4-diazepan-1-yl)benzylamine	HCID 18525905	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Product	2-[4-(4-Methylhexahydro-1,4-diazepin-1-yl)-benzylamino]-N-(5-chloropyridin-2-yl)pyridine-3-carboxamide	HCID 21075305	8.5%

Reaction Steps

A mixture of 2-chloro-N-(5-chloropyridin-2-yl)pyridine-3-carboxamide (1.00 g, 3.7 mmol) and 4-(4-methylhexahydro-1,4-diazepin-1-yl)benzylamine (0.63 g, 2.9 mmol), in 5 mL of DMSO, was heated in a sealed tube at 70–75° C. for 35 h. This reaction mixture was diluted with 250 mL of water, basified with 2 N NaOH, and extracted with ethyl acetate and evaporated to give 0.83 g crude product. Flash chromatography purification with 10% MeOH—CHCl3, 1% NH4OH gave the title product (0.11 g, 8.5%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07163938B2
Source dataset	uspto-grants-2007_01
ORD ID	ord-bde3b6a3f003469ba749fb886bc0b557
Source note	uspto-grants-2007_01