4-(Dimethylamino)Benzaldehyde → (4-{6-Chloro-7-[4-(2-phenoxy-ethyl)-piperazin-1-yl]-3H-imidazo[4,5-b]pyridin-2-yl}-phenyl)-dimethyl-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-3-nitro-4-[4-(2-phenoxy-ethyl)-piperazin-1-yl]-pyridin-2-ylamine (0.037 g, 0.10 mmol), ethanol (3 ml), and 4-dimethylamino-benzaldehyde (0.021 g, 0.14 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.4 ml, 0.4 mmol). The reaction mixture was heated at 70° C. for 5.5 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column, which was eluted with 1 to 2.5% gradient of methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was isolated as a pale yellow solid after trituration with diethyl ether (0.011 g, 23%); %); 1H-NMR (500 Mz, DMSO-d6) 2.72 (br s, 4H, piperazine N(CH2)2), 2.79 (t, J=5.46 Hz, 2H, NCH2CH2O), 3.68 (br s, 4H, piperazine N(CH2)2), 4.15 (t, J=5.70 Hz, 2H, NCH2CH2O), 6.82 (d, J=10.17 Hz, 2H) and 8.00 (d, J=8.93 Hz, 2H) (3,5-C6H4—NMe2 and 3,5-C6H4—NMe2) 6.93 (t, J=6.7 Hz, 1H, p-ArH), 6.99 (d, J=8.92 Hz, 2H, o-ArH), 7.30 (t, J=8.16 Hz, 2H, m-ArH), 8.03 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.10 (s, 1H, imidazo[4,5-b]pyridine N—H); LC-MS (ESI, m/z) 5.57 min—477, 479 [(M+H)+, Cl isotopic pattern]; ESI-HRMS: Found: 477.2162, calculated for C26H30N6OCl (M+H)+: 477.2170.

Provenance & Evidence