1-Hydroxybenzotriazole → [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Decahydroquinoline	HCID 92911	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid	HCID 86630058	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone	HCID 86630061	98.3%

Reaction Steps

To a solution of 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid (1 g, 0.00433 mol) in dry DMF (7.0 mL) was added with stirring HOBt (0.876 g, 0.00649 mol), DIPEA (2.25 mL, 0.0129 mol), decahydroquinoline (0.902 g, 0.00649 mol) at 0° C. To the resulting mixture was added EDCl (1.24 g, 0.00649 mol) and stirred for 15 h at an ambient temperature. The reaction mixture was diluted with ice water (100 mL) and extracted with EtOAc (3×50 mL). The combined organic phases were washed with water, dried (Na2SO4) and the solvent evaporated to give [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone (1.5 g, 98%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08053431B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-9b74c64754f34a08936a5501c2d14352
Source note	uspto-grants-2011_11