Diisopropylethylamine → 2-(4-Chloro-3-(trifluoromethyl)phenyl)-N-(1-oxo-2-(pyridin-2-ylmethyl)-1,2-dihydroisoquinolin-5-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-amino-2-(pyridin-2-ylmethyl)isoquinolin-1(2H)-one (100.00 mg, 0.4 mmol) in N,N-dimethylformamide (0.7 mL, 0.009 mol) was added 2-(4-chloro-3-(trifluoromethyl)phenyl)acetic acid (190 mg, 0.000796 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (303 mg, 0.000796 mol) and N,N-diisopropylethylamine (277 uL, 0.00159 mol). The reaction mixture was stirred for 16 hours at 50° C. Checked LC/MS, the reaction was completed. The DMF reaction solution was directly applied to prep. HPLC to obtain the pure product (134.2 mg). MS m/z=472.3 (M+1). 1H NMR (DMSO) δ 10.13 (s, 1 H), 8.48 (d, J=4.8 Hz, 1 H), 8.06 (d, J=7/9 Hz, 1 H), 7.90 (s, 1 H), 7.84 (d, J=7.1 Hz, 1 H), 7.76 (td, J=7.7, 1.8 Hz, 1 H), 7.75-7.68 (m, 2 H), 7.63 (d, J=7.7 Hz, 1 H), 7.47 (t, J=7.9 Hz, 1 H), 7.32-7.22 (m, 2 H), 6.73 (d, J=7.6 Hz, 1 H), 5.28 (s, 2 H), 3.93 (s, 2 H).

Provenance & Evidence