Dimethylformamide → N-{4-[(Pyridin-3-yl)oxy]phenyl}-1H-benzimidazole-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Benzimidazolecarboxylic acid	HCID 233240	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Solvent	Water	HCID 962	—
Product	N-{4-[(Pyridin-3-yl)oxy]phenyl}-1H-benzimidazole-2-carboxamide	HCID 58858400	—

Reaction Steps

0.064 mmol of benzimidazolecarboxylic acid 4l was dissolved in DMF together with 0.064 mmol of the amine 5b, a solution of TBTU (0.096 mmol) in DMF, HOBT (0.026 mmol) in DMF and 0.32 mmol of DIPEA were added successively, and the mixture was stirred at room temperature. After 2.5 hours, 0.2 eq. of acid was added, and the mixture was stirred overnight. The reaction mixture was diluted with water and extracted a number of times with ethyl acetate. The combined organic phases were washed 2× with water, dried, filtered and evaporated.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07691870B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-69307ef932164e5c93bcd40d0d69f99a
Source note	uspto-grants-2010_04