1-Hydroxybenzotriazole → N-(1H-benzimidazol-2-ylmethyl)-2-(5-chloro-2-oxo-1,3-benzothiazol-3 (2H)-yl)-N-methylacetamide

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	((1H-1,3-benzodiazol-2-yl)methyl)(methyl)amine dihydrochloride	HCID 13169407	—
Reactant	2-(5-chloro-2-oxobenzo[d]thiazol-3(2H)-yl)acetic acid	HCID 13174335	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(1H-benzimidazol-2-ylmethyl)-2-(5-chloro-2-oxo-1,3-benzothiazol-3 (2H)-yl)-N-methylacetamide	HCID 117652708	79.7%

Reaction Steps

To a mixture of (5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)acetic acid (731 mg), 1-(1H-benzimidazol-2-yl)-N-methylmethanamine dihydrochloride (736 mg), and dichloromethane (20 mL) were added HOBt (448 mg), WSC.HCl (633 mg), and TEA (1.05 mL), followed by stirring at room temperature overnight. The resulting solid was collected by filtration and then washed with chloroform to obtain N-(1H-benzimidazol-2-ylmethyl)-2-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-methylacetamide (925 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08937087B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-b694ecd8f6214ec4b413235f84cc687d
Source note	uspto-grants-2015_01