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0 °C

A suspension of 3-[7-(2-chloroethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid (425 mg) in methylene chloride (8 ml) was cooled to 0° C. and oxalyl chloride (0.2 ml) was added followed by DMF (10 μL) and the reaction mixture was left to stir at room temperature for 1 hour when N,N′-diisopropylethylamine (0.8 ml) and ethylamine (2.28 ml of a 2.0M in THF) were added. The reaction mixture was stirred at room temperature for 17 hours and concentrated. The residue was diluted with ethyl acetate and washed with water (×3), brine, dried (magnesium sulfate) and concentrated to a brown foam which was purified by column chromatography on a silica column eluting using a gradient of iso-hexane to ethyl acetate to give 3-[7-(2-chloroethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide as a pale yellow solid (323 mg); NMR Spectrum: (DMSOd6) 1.11 (t, 3H), 2.11 (s, 3H), 2.27 (s, 3H), 3.28 (m, 2H), 4.01 (t, 2H), 4.41 (m, 2H), 7.13 (s, 1H), 7.52 (m, 2H), 7.73-7.78 (m, 3H), 7.89 (d, 1H), 8.50 (t, 1H); Mass Spectrum: M+H+ 399.

1. waitthe reaction mixture was left
2. additionwere added
3. concentrationconcentrated
4. additionThe residue was diluted with ethyl acetate
5. washwashed with water (×3), brine
6. dry with materialdried (magnesium sulfate)
7. concentrationconcentrated to a brown foam which
8. customwas purified by column chromatography on a silica column
9. washeluting