HCID 18761417, compound → HCID 11282958, compound

Participants

Reaction Steps

A solution of 2-[4-(N-benzyloxycarbonylamino)-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate (0.1 g, 0.16 mmol) in THF (10 mL) was added to a suspension of 10% Pd/C (0.1 g) in chilled THF (10 mL) and the suspension was hydrogenated under H2 atmosphere at room temperature for 3 days. The suspension was filtered over Celite and the filtrate was concentrated in reduced pressure. The residue was crystallized with diisopropylether to yield 2-[4-amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate (0.064 g, 84%) as a white solid: mp 182-186° C. (decomp.); 1H NMR (CDCl3, 500 MHz) δ 9.40 (s, 1H), 8.65 (s, 1H), 7.94 (d, 8.5, 1H), 7.86 (d, 8.5, 1H), 7.57 (s, 1H), 7.55 (t, 8.0, 1H), 7.46 (t, 8.0, 1H), 7.19 (brs, 1H), 6.88 (s, 1H), 4.39 (t, 7.0, 2H), 4.23 (brs, 2H), 4.10 (s, 3H), 3.96 (s, 3H), 3.93 (s, 3H), 3.41 (t, 7.0, 2H), 2.10 (s, 1.5, 3H); FABMS (NBA) m/z 478 (M+H+), IR (neat) νmax 3341, 1727, 1639, 1591, 1536, 1505, 1466, 1410, 1304, 1243, 1106, 1046, 758 cm−1.

Provenance & Evidence