反应详情

To a solution of 3-(7-amino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester (0.180 g, 0.602 mmol) and pyridine (0.052 g, 0.662 mmol) in dichloromethane (2 mL) is added acetyl chloride (0.052 g, 0.662 mmol) at 0° C. and the reaction is stirred for 2.5 hours. The solution is then washed with 10% aqueous HCl and water and the combined aqueous phases are extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered, and concentrated to give a residue, which is purified by silica gel chromatography (dichloromethane-methanol mixtures) to give 3-(7-acetylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 342.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.39 (d, J=6.3 Hz, 3 H), 1.40 (d, J=6.3 Hz, 3 H), 1.78-1.92 (m, 2 H), 2.08 (s, 3 H), 2.16-2.31 (m, 2 H), 2.81-2.89 (m, 1 H), 2.98 (dt, J=16.9, 6.1 Hz, 1 H), 5.25 (sept, J=6.3 Hz, 1 H), 6.32 (t, J=5.4 Hz, 1 H), 7.17 (br. s, 1 H), 7.22 (d, J=8.3 Hz, 1 H), 7.43 (s, 1 H), 7.50 (dd, J=8.3, 2.1 Hz, 1 H), 7.74 (d, J=1.0 Hz, 1 H).

1. washThe solution is then washed with 10% aqueous HCl and water
2. extractionthe combined aqueous phases are extracted with ethyl acetate
3. dry with materialThe combined organic phases are dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a residue, which
7. customis purified by silica gel chromatography (dichloromethane-methanol mixtures)