Potassium Iodide → HCID 67018589, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[7-(2-chloroethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide and 3-[7-(2-bromoethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide (4:1, 225 mg), potassium iodide (182 mg), and N-methylisopropylamine (0.34 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 initially 10% methanol/ethyl acetate and then a 99:1 mixture of 10% methanol/ethyl acetate and aqueous ammonia solution gave N-cyclopropyl-3-[7-{2-[isopropyl(methyl)amino]ethoxy}-4-methyl-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzamide (105 mg) as a pale yellow foam; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 0.97 (d, 6H), 2.10 (s, 3H), 2.24 (s, 3H), 2.27 (s, 3H), 2.76 (t, 2H), 2.80-2.89 (m, 2H), 4.14 (m, 2H), 7.09 (s, 1H), 7.45-7.51 (m, 2H), 7.70-7.75 (m, 3H), 7.86 (d, 1H), 8.45 (d, 1H); Mass Spectrum: M+H+ 448.

Provenance & Evidence