2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 59799758, compound

Participants

Reaction Conditions

Reaction Steps

N1-[2-(1-Methyl-pyrrolidin-2-yl)-ethyl]-4-nitro-benzene-1,2-diamine 32 (0.396 g, 1.498 mmol) was dissolved in anhydrous chloroform (20 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (0.284 g, 1.573 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.455 g, 1.841 mmol) are added quickly as solids and resulting solution heated in an oil bath at 35° C. for 18 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and chloroform and 2M ammonium hydroxide solution added to adjust pH to 10. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with chloroform and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated to afford crude solid. The product was purified using silica gel dry column chromatography with a solvent system of (5% 2M NH3 in methanol/95% dichloromethane) to afford a yellow powder 33 2-(4-Ethoxy-phenyl)-N-{2-[2-(1-methyl-pyrrolidin-2-yl)-ethylamino]-5-nitro-phenyl}-acetamide Yield: 0.115 grams (18.0%). 1H NMR (DMSO) δ: 1.31 (t, 3H, J=7.0), 1.43-1.68 (2×m, 4-5H), 1.78-1.91 (m, 2H), 2.01-2.10 (m, 1H), 2.12-2.19 (m, 1H), 2.22 (s, 3H), 2.89-2.99 (m, 1H), 3.19-3.30 (m, 2H), 3.61 (s, 2H), 4.00 (q, 2H, J=6.9), 6.57 (br, 1H), 6.70 (d, 1H, J=9.1), 6.88 (d, 2H, J=8.4), 7.24 (d, 2H, J=8.6), 7.94 (dd, 1H, J=9.1, 2.6), 7.99 (d, 1H, J=2.5), 9.43 (br s, 1H); MS (ESI): 427 (MH+, 100%).

Provenance & Evidence