Oxalyl chloride → 3-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamide

Participants

Reaction Steps

Reaction of acid (117) prepared as described in example 230 with oxalyl chloride followed by histamine using the procedure described in example 207 gave the amide (128) (81%) as a yellow powder, mp 144–149° C. (dec). 1H NMR δ [(CD3)2SO] 11.12 (br, 1H), 8.52 (d, J=2.6 Hz, 1H), 7.91 (t, J=5.5 Hz, 1H), 7.76 (s, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.58 (m, 1H), 7.52–7.42 (m, 4H), 7.32 (dd, J=9.0, 2.6 Hz, 1H), 6.56 (s, 1H), 4.69 (t, J=6.4 Hz, 2H), 3.90 (s, 3H), 3.12 (m, 2H), 2.58 (t, J=6.4 Hz, 2H), 2.39 (t, J=7.4 Hz, 2H). Found: C, 60.73; H, 4.49; N, 11.49. C29H24ClN5O4. 1/2CH2Cl2 requires C, 60.62; H, 4.31; N, 11.98.

Provenance & Evidence