1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(3-Pyrid-4-ylpropionamido)-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

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Reaction Steps

EDAC (0.035 g, 0.18 mmol) was added to a solution of 3-amino-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole (Method 5; 0.03 g, 0.12 mmol), DMAP (0.007 g, 0.06 mmol) and 3-(pyridin-4-yl)propanoic acid (Method 6; 0.027 g, 0.18 mmol) in DMF (10 ml). The mixture was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane and a saturated solution of sodium bicarbonate. The organic layer was separated, washed with brine, dried over magnesium sulphate and then evaporated to dryness in vacuo. The crude product was purified by flash chromatography eluting over a gradient of 0-10% MeOH in DCM. NMR (CDCl3) 8.72 (s, 1H), 8.51 (m, 2H), 8.19 (d, 1H), 7.59 (d, 2H), 7.47 (s, 1H), 7.29 (m, 1H), 7.20 (m, 2H), 5.05 (m, 1H), 3.12 (m, 4H), 2.78 (m, 2H), 1.73 (d, 6H), 1.31 (t, 3H); m/z 388.

Provenance & Evidence