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

関与物質

反応手順

(1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (1.30 mg, 0.386 mmol), 4-(dimethylamino)benzaldehyde (63.3 mg, 0.424 mmol) and ammonium acetate (59.4 mg, 0.771 mmol) were heated in ethanol (5 mL) at 70° C. for 18 hours. The desired product precipitated from the reaction mixture. The mixture was diluted with ethyl ether (5 mL) and filtered. The remaining solid was dried under high vacuum to afford 85 mg (47%) of the title compound. mp: 264-265° C., 1H NMR (300 MHz, DMSO-d6): 12.73 (s, 1H), 7.96 (d, J=8 Hz, 2H), 7.84 (d, J=4 Hz, 1H), 7.65 (s, 1H), 7.15 (s, 1H), 6.81 (d, J=8 Hz, 2H), 6.70 (d, J=8 Hz, 1H), 6.37 (d, J=8 Hz, 1H), 6.32 (s, 2H), 3.89 (br s, 1H), 2.99 (s, 6H), 2.87 (s, 1H), 2.75 (s, 1H), 2.60 (d, J=7 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 1.42 (d, J=8 Hz, 1H). MS: 467, 469 (M+H), HPLC: 2.43 min (G method).

情報源と証拠