N,N,N',N'-Tetramethylethylenediamine → 2-[(5S)-3-(6-Cyanopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide

Participants

Role	Name	HCID	Charge
Reactant	N,N,N',N'-Tetramethylethylenediamine	HCID 8037	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	HCID 86705191	HCID 86705191	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-[(5S)-3-(6-Cyanopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide	HCID 86705190	—

Reaction Steps

A solution of 2-[(5S)-3-(6-bromopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide (150 mg), zinc cyanide (91 mg), Pd2(dba)3 (8.5 mg), Xantphos (11 mg), and N,N,N′,N′-tetramethylethylenediamine (14 μL) in DMF (2 mL) was stirred under irradiation with microwave at 180° C. for 30 min. Additional zinc cyanide (91 mg) was added thereto, and the resulting mixture was stirred under the same condition for 30 min. NH silica gel was added thereto, the mixture was stirred, followed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC to afford the title compound (47 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08796272B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-6f2612134ae34eff86681ce0d3c70f23
Source note	uspto-grants-2014_08