Potassium Iodide → N-cyclopropyl-4-methyl-3-[7-[2-(1,4-oxazepan-4-yl)ethoxy]-1-oxoisoquinolin-2(1H)-yl]benzamide

Participants

Reaction Conditions

Reaction Steps

3-[7-(2-Chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide (0.15 g), potassium iodide (0.13 g), 1,4-oxazepane hydrochloride (0.34 g), and N,N′-diisopropylethylamine (0.8 ml) were stirred in DMA (3 ml) and heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 150° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with water (×5), brine (×2), dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting using a gradient of ethyl acetate to 15% methanol/ethyl acetate gave N-cyclopropyl-4-methyl-3-[7-[2-(1,4-oxazepan-4-yl)ethoxy]-1-oxoisoquinolin-2(1H)-yl]benzamide (0.114 g) as a white solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 1.80 (m, 2H), 2.10 (s, 3H), 2.76 (m, 4H), 2.85 (m, 1H), 2.92 (t, 2H), 3.61 (m, 2H), 3.66 (t, 2H), 4.19 (m, 2H), 6.72 (d, 1H), 7.21 (d, 1H), 7.41 (d, 1H), 7.49 (d, 1H), 7.69 (s, 1H), 7.71 (d, 1H), 7.74 (s, 1H), 7.88 (d, 1H), 8.43 (d, 1H); Mass Spectrum: M+H+ 462.

Provenance & Evidence