1-Adamantanecarbonyl chloride → Adamantane-1-carboxylic acid [2-(4-adamantanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

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Reaction Steps

To a solution of amine 14 (0.200 g, 0.50 mmol) in dry THF-Pyridine (10 ml/0.400 ml), adamantane carbonyl chloride (0.150 g, 0.75 mmol) was added and stirred at room temperature under argon overnight. The reaction was quenched with water and stirred at room temperature for 30 min. The yellow solid was filtered and passed through SiO2 gel using CH2Cl2: MeOH (95:5) as a eluent that yielded the desired product 15 (0.150 g, 50%). M.p. 265° C.; 1HNMR (DMSO-d6, 500 MHz): δ 13.02 (1H, brs, NH), 9.48 (1H, brs, NH), 9.37 (1H, brs, NH), 8.64 (1H, s), 8.24 (1H, s), 8.08 (2H, d, J=5.0 Hz), 7.88 (2H, d, J=5.0 Hz), 2.03-1.60 (30H, m). EIMS m/z: 449.6 (M+1); Anal (C34H39N5O2×0.85 H2O) C, H, N.

Provenance & Evidence