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

Participants

Reaction Steps

To a stirring solution of 10 (0.080 g, 0.24 mmol) in dry THF/Pyridine (10 ml/0.300 ml) cyclohexane carbonyl chloride (0.060 ml, 0.38 mmol) was added and stirred at room temperature for 4 h. The reaction mixture was quenched with water and stirred for 30 min. The yellow solid was filtered, dried, and purified through a bed of SiO2 gel. Elution with ethyl acetate afforded the desired product 11 as light yellow solid 0.055 g (51%). Mp. 235° C.; 1HNMR (DMSO-d; 500 MHz): δ 12.99 (1H, brs, NH), 10.27 (1H, brs, NH), 10.07 (1H, brs, NH), 8.61 (1H, brs), 8.27 (1H, brs), 8.07 (2H, d, J=8.0 Hz), 7.79 (2H, d, J=9.0 Hz); 2.52 (1H, m), 2.36 (1H, m), 1.83-1.17 (20H, m); EIMS m/z: 446.5 (M+1) 444.6 (M−1); Anal. (C26H31N5O2.0.91H2O) C, H, N

Provenance & Evidence