Cyclohexanecarbonyl chloride → Cyclohexanecarboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

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Reaction Steps

To a stirring solution of 8 (0.116 g, 0.45 mmol) in dry THF and Pyridine (10 ml/0.300 ml), cyclohexanecarbonyl chloride (0.100 ml, 0.68 mmol) was added and stirred at room temperature for 4 h. The reaction was quenched by the addition of water and the yellow solid was filtered, air-dried and dissolved in EtOAc and passed through a bed of SiO2 gel. Elution with EtOAc afforded the desired product 9 (0.095 g, 58%). 1H NMR (DMSO-d6, 500 MHz): δ 13.49 (1H, s), 10.38 (1H, s, NH), 8.76 (1H, s), 8.41 (4H, dd, J=15 and 5 Hz); 8.34 (1H, s), 2.53 (1H, m), 1.80-1.20 (10, m); MS m/z: 366 (M+1), 364 (M−1). The product was used for the next step.

Provenance & Evidence