Water → HCID 9821385, compound

Participants

Reaction Conditions

Reaction Steps

3-Azidomethyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-carboxylic acid ethyl ester (49 mg) and triphenylphosphine (50 mg) were dissolved in THF (2.5 ml). To the solution was added water (0.3 ml) and the mixture was heated to 70° C. overnight. The reaction mixture was diluted with ethyl acetate (5 ml) and washed with brine (5 ml), then dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography developed by dichloromethane-methanol giving 3-aminomethyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-carboxylic acid ethyl ester as a colorless oil (15 mg). FAB-MS: m/z 384 (MH+); 1H-NMR (CDCl3): δ 1.45 (3H, t, J=7.3 Hz), 2.12 (2H, quintet, J=6.3 Hz), 2.90 (2H, t, J=6.6 Hz),3.85 (2H, s), 4.24 (2H, t, J=6.3 Hz), 4.31 (2H, s), 4.45 (2H, q, J=7.3 Hz), 6.68 (1H, d, J=8.3 Hz), 7.16 (1H, d, J=8.3 Hz), 7.21 (1H, dd, J=4.9 Hz, 7.9 Hz), 7.35 (1H, t, J=8.3 Hz), 7.68 (1H, d, J=7.9 Hz), 8.48 (1H, dd, J=1.7 Hz, 4.9 Hz), 8.56 (1H, d, J=1.7 Hz).

Provenance & Evidence