Dimethylformamide → (S)-tert-Butyl 3-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

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	(S)-tert-butyl 3-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate	HCID 66649434	—
Product	(S)-tert-Butyl 3-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate	HCID 66649399	—

Reaction Conditions

Temperature	45 °C

Reaction Steps

A reaction vial was charged with (S)-tert-butyl 3-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate (150.00 mg, 0.043678 mmol), 2-(3-fluoro-4-(trifluoromethyl)phenyl)acetic acid (116.4 mg, 0.05241 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (420 mg, 1.1 mmol), N,N-diisopropylethylamine (0.19 mL, 1.1 mmol) and N,N-dimethylformamide (2 mL, 20 mmol) and the reaction was stirred at 45° C. overnight. The solvent was removed under reduced pressure and the residue purified by flash chromatography to afford the product as light yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093265B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-ac73c5bfa2c94d85bf27df09fcf15ede
Source note	uspto-grants-2012_01