1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-Cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (1-hydroxymethyicyclopentylmethyl)amide

Participants

Reaction Steps

5-Cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (200 mg, 0.56 mmol), 1-hydroxymethyl-cyclopentanecarbonitrile (145 mg, 1.12 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (117 mg, 0.61 mmol) and 1-hydroxybenzotriazole hydrate (83 mg, 0.61 mmol) were stirred in DCM (20 ml) for 66 h at room temperature. The reaction was poured into water (25 ml) and diluted with DCM (25 ml). The organic layer was isolated using a hydrophobic filter tube and the DCM removed under reduced pressure and purified by semi-preparative HPLC followed by purification on neutral alumina giving the title compound (75 mg, 28%) as a glassy solid.

Provenance & Evidence