Potassium Iodide → N-ethyl-3-[7-{2-[isopropyl(methyl)amino]ethoxy}-4-methyl-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzamide

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Reaction Conditions

Reaction Steps

A mixture of 3-[7-(2-chloroethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide (90 mg), potassium iodide (75 mg), and N-methylisopropylamine (0.14 ml) were stirred in DMA (2 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 initially 10% methanol/ethyl acetate and then a 99:1 mixture of 110% methanol/ethyl acetate and aqueous ammonia solution gave N-ethyl-3-[7-{2-[isopropyl(methyl)amino]ethoxy}-4-methyl-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzamide (68 mg) as a cream solid; NMR Spectrum: (DMSOd6) 0.98 (d, 6H), 1.12 (t, 3H), 2.11 (s, 3H), 2.25 (s, 3H), 2.27 (s, 3H), 2.78 (t, 2H), 2.85 (m, 1H), 3.29 (m, 2H), 4.15 (m, 2H), 7.10 (s, 1H), 7.45-7.51 (m, 2H), 7.70-7.77 (m, 3H), 7.88 (d, 1H), 8.47 (t, 1H); Mass Spectrum: M+H+ 436.

Provenance & Evidence