Potassium Carbonate → Pyridine-2-carboxylic acid [2-(4-adamantanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amide

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Reaction Steps

A solution of 22 (0.065 g, 0.197 mmol), adamantane carbonyl chloride (0.060 g, 0.30 mmol) in dry Pyridine (5 ml) was stirred at 80° C. for 2 h. After usual work-up the solid was treated with 10% K2CO3 for 1 h. The solid was filtered and passed through SiO2 gel, eluting with EtOAc affording diamide 24 (0.039 g, 40%). M.p. 305° C.; 1H NMR (DMSO-d6, 500 MHz): δ 13.19 (1H, brs, NH), 10.47 (1H, brs, NH), 9.39 (1H, brs), 8.765 (1H, d, J=4.5 Hz), 8.73 (1H, brs), 8.45 (1H, brs), 8.24 (1H, d, J=8.0 Hz), 8.14-8.09 (2H, m), 7.89 (2H, d, J=8.5 Hz), 7.72 (1H, dt, J=5.0 and 7.5 Hz), 2.0 (3H, brs), 1.92 (6H, brs), 1.72 (6H, brs); EIMS m/z: 493.5 (M+1); Anal (C29H28N6O2×1.23 H2O) C, H, N.

Provenance & Evidence