Dimethylformamide → (R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Fluoro-4-(trifluoromethyl)phenylacetic acid	HCID 2737591	—
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	(R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate	HCID 59515683	—
Product	(R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate	HCID 59515877	—

Reaction Conditions

Temperature	45 °C

Reaction Steps

A round bottom flask was charged with (R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (175 mg, 0.000638 mol), 2-(3-fluoro-4-(trifluoromethyl)phenyl)acetic acid (210 mg, 0.00096 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (610 mg, 0.0016 mol), N,N-diisopropylethylamine (0.28 mL, 0.0016 mol) and N,N-dimethylformamide (8 mL, 0.1 mol) and the reaction stirred at 45° C. for 24 hours. The reaction did not go to completion. The reaction was then quenched with water and extracted with ethyl acetate, washed with NaHCO3, brine and dried. The solvent was removed under reduced pressure and the residue purified by flash chromatography to obtain the product as a light yellow oil. MS m/z=479.3 (M+H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07816371B2
Source dataset	uspto-grants-2010_10
ORD ID	ord-94f206ab961e4581854ce3f3bcfc28e7
Source note	uspto-grants-2010_10