Diisopropylethylamine → HCID 66832275, compound

https://huagongshe.com/reaction/1918764

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	5-(2,5-Difluorobenzyl)isoxazole-3-carboxylic acid	HCID 66832039	—
Reactant	2-(5-chloro-1H-pyrrolo(2,3-b)pyridin-3-yl)ethan-1-amine hydrochloride	HCID 66832061	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 66832275	HCID 66832275	41.5%

Reaction Steps

The mixture of 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine hydrochloride (0.070 g; 0.301 mmol), 5-(2,5-difluorobenzyl)isoxazole-3-carboxylic acid (0.073 g; 0.304 mmol), HATU (N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate) (0.116 g: 0.304 mmol) and N,N-diisopropylethylamine (0.132 mL; 0.754 mmol) in DMF (3 mL) was stirred for 72 hours at room temperature and was concentrated under reduced pressure. The residue was dissolved in dichloromethane and the organic layer was washed with water and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent: 0 to 35% of ethyl acetate in dichloromethane) to give 0.051 g (40%) of N-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08618138B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-aa4f474af9454b7195e3907bb9efbe88
Source note	uspto-grants-2013_12