4-Methoxybenzaldehyde → (1S,2S,3R,4R)-3-[6-Chloro-2-(4-methoxy-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Participants

Reaction Steps

In the same fashion as for Compound III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 4-methoxybenzaldehyde were reacted to produce the title compound (16%). 1H NMR (d-chloroform): 15.54 (br s, 1H) 8.23 (d, J=9 Hz, 1H), 8.06 (d, J=9 Hz, 2H), 7.79 (s, 1H), 7.06 (d, J=9 Hz, 2H), 6.51 (m, 1H), 6.42 (m, 1H), 5.86 (br s, 1H), 5.46 (br s, 1H), 5.39 (t, J=8 Hz, 1H), 3.91 (s, 3H), 3.17 (s, 1H), 3.05 (s, 1H), 2.68 (d, J=9 Hz, 1H), 2.33 (d, J=9 Hz, 1H), 1.68 (d, J=10 Hz, 1H). MS: 466.07 (M+H). HPLC retention time: 2.42 minutes (G Method).

Provenance & Evidence