1,1'-Carbonyldiimidazole → N-[(1S,2R)-2-aminocyclohexyl]-4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxamide

Participants

Reaction Steps

To a solution of 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylic acid (10.0 mg, 0.029 mmol) in N,N-dimethylformamide (1 ml) was added 1,1′-carbonyldiimidazole (7.0 mg, 0.043 mmol). After 20 minutes cis-1,2-cyclohexanediamine (0.034 ml, 0.29 mmol) was added. After 10 minutes the reaction mixture was purified directly by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give N-[(1S,2R)-2-aminocyclohexyl]-4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxamide. 1H NMR (600 MHz, DMSO-d6) δ 8.13 (s, 1H); 7.85 (d, 2H); 7.74 (d, 1H); 7.59 (s, 1H); 7.54 (d, 1H); 7.47-7.49 (m, 2H); 7.38-7.41 (m, 1H); 6.66 (d, 1H); 3.99 (s, 3H); 1.50-1.72 (m, 7H); 1.29-1.36 (m, 3H). LRMS (ESI) calculated for C25H27N4O2S [M+H]+, 447.2 found 447.1.

Provenance & Evidence