Dimethylformamide → (S)-2-(5-(2-(3,4-Dichlorophenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propanamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	3,4-Dichlorophenylacetic acid	HCID 79874	—
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	(S)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propanamide	HCID 59515789	—
Product	(S)-2-(5-(2-(3,4-Dichlorophenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propanamide	HCID 59515801	—

Reaction Steps

To a stirred solution of 3,4-dichlorophenyl acetic acid (0.12 g, 0.00056 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.3 g, 0.0009 mol) and N,N-diisopropylethylamine (0.2 mL, 0.0009 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was added (S)-2-(5-amino-1-oxoisoquinolin-2(1H)-yl)propanamide (0.10 g, 0.00043 mol). The reaction was stirred for 16 h at room temperature. The reaction was quenched with water, extracted with dichloromethane, washed with 2N HCl, saturated sodium bicarbonate solution, brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (12 g, 0-10% MeOH/DCM) to yield the product as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07816371B2
Source dataset	uspto-grants-2010_10
ORD ID	ord-191b786f13184b5dbcc374cc276072ef
Source note	uspto-grants-2010_10