Pyridine → HCID 59199363, compound

Participants

Reaction Steps

To a solution of 3-(7-amino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester, which can be prepared as described as in Example 45, (0.408 g, 1.36 mmol) and pyridine (0.162 g, 2.04 mmol) in dichloromethane (4 mL) at 0° C. is added methanesulfonyl chloride (0.168 g, 1.47 mmol) 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-methanesulfonylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 378.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.38 (d, J=6.3 Hz, 3 H), 1.40 (d, J=6.3 Hz, 3 H), 1.84-1.93 (m, 2 H), 2.19-2.33 (m, 2 H), 2.87 (dt, J=16.9, 6.6 Hz, 1 H), 2.88 (s, 3 H), 3.01 (dt, J=16.9, 6.3 Hz, 1 H), 5.24 (sept, J=6.3 Hz, 1 H), 6.32 (t, J=6.1 Hz, 1 H), 6.81 (d, J=2.0 Hz, 1 H), 7.21 (dd, J=8.3, 2.0 Hz, 1 H), 7.26 (d, J=8.3 Hz, 1 H), 7.51 (s, 1 H), 7.75 (d, J=1.0 Hz, 1 H).

Provenance & Evidence