4-Morpholinobenzaldehyde → (1S,2S,3R,4R)-3-[6-Chloro-2-(4-morpholin-4-yl-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-morpholin-4-yl-benzaldehyde were reacted to produce the title compound (20%). 1H NMR (d-chloroform): 15.43 (br s, 1H), 8.06 (d, J=9 Hz, 1H), 8.00 (d, J=9 Hz, 2H), 7.77 (s, 1H), 7.02 (d, J=9 Hz, 2H), 6.50 (m, 1H), 6.42 (m, 1H), 5.91 (br s, 1H), 5.53 (br s, 1H), 5.40 (t, J=8 Hz, 1H), 3.90 (t, J=5 Hz, 4H), 3.30 (t, J=5 Hz, 4H), 3.17 (s, 1H), 3.04 (s, 1H), 2.68 (d, J=8 Hz, 1H), 2.38 (d, J=9 Hz, 1H), 1.67 (d, J=9 Hz, 1H). MS: 466.07 (M+H). HPLC retention time: 2.42 minutes (G Method).

Provenance & Evidence