4-(Dimethylamino)Benzaldehyde → HCID 178482691, compound

Participants

Reaction Steps

(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (77 mg, 0.26 mmol) and 4-(dimethylamino)benzaldehyde (54 mg, 0.36 mmol) were combined and heated in 8 mL nitrobenzene at 140° C. for six hours. The reaction was concentrated and purified by reverse phase chromatography on a Gilson chromatograph to afford 16 mg (14%) of the title compound. 1H NMR (d-chloroform): 13.55 (br s, 1H), 7.99 (m, 3H), 6.84 (m, 2H), 6.62 (br s, 1H), 6.36 (m, 2H), 5.45 (d, J=9 Hz, 1H), 5.37 (s, 1H), 5.21 (t, J=9 Hz, 1H), 3.19 (s, 1H), 3.11 (s, 6H), 2.92 (m, 2H), 2.35 (d, J=9 Hz, 1H), 1.76 (d, J=9 Hz, 1H). MS: 424.05 (M+H). HPLC retention time: 2.39 minutes (G Method).

Provenance & Evidence