Acetic Acid → HCID 67575036, compound

Participants

Reaction Steps

To a solution of 2-[(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)amino]ethyl carbamic acid tert-butyl ester (0.42 g, 1.2 mmol) in methanol (10 ml) at 0° C. was added benzaldehyde (133 μl, 1.3 mmol), acetic acid (189 μl, 3.3 mmol) and sodium cyanoborohydride (137 mg, 2.2 mmol). After addition the cooling bath was removed and the mixture stirred for 4 h. After this time more benzaldehyde (110 μl, 1.1 mmol) was added and the mixture stirred for 18 h. More benzaldehyde (110 μl, 1.1 mmol) was added and the mixture stirred for a further 10 min. The solvents were evaporated and the residue partitioned between EtOAc (2×50 ml) and water (50 ml). The combined organic layers were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH:NH3 (95:5:1), to give the desired product (0.44 g, 85%) as a pale yellow foam. 1H NMR (360 MHz, CDCl3) δ1.41 (9H, s), 1.84-1.96 (2H, m), 2.52-2.58 (4H, m), 2.75 (2H, t, J=7.5 Hz), 3.12-3.20 (2H, m), 3.58 (2H, s), 4.78 (1H, br s), 7.03 (1H, s), 7.14 (1H, dd, J=8.5 and 2.0 Hz), 7.21-7.36 (5H, m), 7.45 (1H, d, J=8.5 Hz), 7.51 (1H, d, J=2.0 Hz), 8.29 (1H, br s), 8.45 (2H, s). MS (ES+) (475, M+1).

Provenance & Evidence