Anthranilamide → 9-Bromo-5-(o-carbamoylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Participants

Reaction Steps

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (170 mg, 0.5 mmol) and o-carbamoylaniline (75 mg, 0.55 mmol) to give 180 mg of the title compound (79%): mp 186° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.04 (bs, 1H), 11.64 (s, 1H), 8.38 (d, 1H, J=8.1 Hz), 7.77 (d, 2H, J=8.1 Hz), 7.50 (t, 1H, J=8.1 Hz), 7.21 (s, 1H), 7.14 (s, 1H), 7.12 (t, 1H, J=8.1 Hz), 5.15~5.24 (m, 1H), 3.04 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.67 (dd, 1H, J=14.5, 5.0 Hz), 2.61 (dd, 1H, J=14.5, 9.0 Hz), 2.17 (dm, 1H, J=13.5 Hz), 1.81~1.96 (m, 1H).

Provenance & Evidence