Triethylamine → HCID 178502905, compound

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Hydroxyazetidine	HCID 1514290	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 178524455	HCID 178524455	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 178502905	HCID 178502905	30%

Reaction Steps

A mixture of 2-[3-(5-chloro-1H-benzoimidazol-2-yl)-azetidin-1-yl]-nicotinic acid (100 mg, 0.30 mmol), azetidin-3-ol (200 mg, 2.73 mmol), HATU (347 mg, 0.9 mmol), and Et3N (101 mg, 1 mmol) in dry DCM (10 mL) was stirred at RT overnight. The mixture was then poured into saturated aqueous Na2CO3. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude compound which was purified by column chromatography and followed by preparative HPLC to afford pure product {2-[3-(5-chloro-1H-benzoimidazol-2-yl]-pyridin-3-yl}-(3-hydroxy-azetidin)-methanone (30 mg, yield 30%). [M+1] 384. IC50 (uM) 0.549.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946230B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-905fbf55526d4989a5d35e9fadfaa013
Source note	uspto-grants-2015_02