Trifluoroacetic acid → 6-Chloro-2-(4-(piperazin-1-ylmethyl)phenyl)-7-(4-(pyrimidin-5-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridine

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Reaction Steps

This was prepared using the same procedure as for (4-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)methanamine, but here using tert-butyl 4-(4-(6-chloro-7-(4-(pyrimidin-5-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate (15 mg, 0.025 mmol), TFA (0.2 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (7 mg, 56%) as a pale yellow solid; δH (500 MHz, DMSO-d6) 2.32 (s, br, 4H, piperazine N(CH2)2), 2.64 (s, br, 4H, piperazine N(CH2)2), 2.72 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 3.50 (s, 2H, NCH2), 3.64 (s, 2H, NCH2), 3.70 (t, J=4.5 Hz, 4H, piperazine N(CH2)2), 7.45 (d, J=8.2 Hz, 2H, phenyl H-3 & H-5), 8.11 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.12 (d, J=8.3 Hz, 2H, phenyl H-2 & H-6), 8.80 (s, 2H, pyrimidine H-4 & H-6), 9.12 (s, 1H, pyrimidine H-2);

Provenance & Evidence