Dimethylformamide → 2-(4-chloro-3-(trifluoromethyl)phenyl)-N-(2-(2-(methylsulfonyl)ethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Chloro-3-(trifluoromethyl)phenylacetic acid	HCID 3519882	—
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-Amino-2-(2-(methylsulfonyl)ethyl)isoquinolin-1(2H)-one	HCID 59579607	—
Product	2-(4-chloro-3-(trifluoromethyl)phenyl)-N-(2-(2-(methylsulfonyl)ethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide	HCID 59579468	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of 5-amino-2-(2-(methylsulfonyl)ethyl)isoquinolin-1(2H)-one (30 mg, 0.0001 mol) in N,N-dimethylformamide (700 μL, 0.009 mol) was added 2-(4-chloro-3-(trifluoromethyl)phenyl)acetic acid (51 mg, 0.00021 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (102 mg, 0.000268 mol) and N,N-diisopropylethylamine (93 μL, 0.00054 mol). The reaction mixture was stirred for 16 hours at 50° C. LC-MS analysis showed the formation of the desired product. The mixture was taken up in saturated NaHCO3 solution and washed twice with ethyl acetate. The organic layer was dried with sodium sulfate, reduced in vacuo and purified via HPLC to afford the title compound as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546579B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-4390da3f3d804cb58712a96954872e58
Source note	uspto-grants-2013_10