3-(Morpholinomethyl)benzaldehyde → (1S,2S,3R,4R)-3-[6-Bromo-2-(3-morpholin-4-ylmethyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Participants

Reaction Steps

In a similar fashion to Compound LXXVI, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (40.0 mg, 0.118 mmol) and 3-morpholin-4-ylmethyl-benzaldehyde (26.7 mg, 0.130 mmol) were reacted to produce 35 mg (57%) of the title compound. mp: 184-185° C., 1H NMR (300 MHz, CDCl3): 8.13 (s, 1H), 8.04 (s, 1H), 7.98 (s, 1H), 7.47 (s, 2H), 6.40 (d, J=8 Hz, 2H), 6.24 (s, 1H), 6.14 (br s, 1H), 6.10 (d, J=8 Hz, 1H), 5.28 (t, J=8 Hz, 1H), 3.74 (br s, 4H), 3.64 (s, 2H), 3.17 (s, 1H), 3.07 (s, 6H), 2.94 (s, 1H), 2.80 (d, J=8 Hz, 1H), 2.54 (s, 3H), 2.35 (d, J=8 Hz, 1H), 2.13 (s, 1H), 1.70 (d, J=8 Hz, 1H). MS: 523, 525 (M+H), HPLC: 1.84 min (G method).

Provenance & Evidence