Trifluoroacetic acid → HCID 178509625, compound

Participants

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-(6-bromo-7-(4-phenoxypiperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzylcarbamate (17 mg, 0.029 mmol), TFA (0.25 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (13 mg, 93%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.84-1.90 (m, 2H, 2× piperidine CHAHB), 2.17-2.19 (m, 2H, 2× piperidine CHAHB), 3.61 (ddd, J=12.4, 9.7, 1.8 Hz, 2× piperidine NCHAHA), 3.80 (s, 3H, OCH3), 3.86-3.91 (m, 2H, 2× piperidine NCHAHA), 4.70 (septet, J=4.0 Hz, 1H, piperidine CH), 6.94 (t, J=7.3 Hz, 1H, phenyl H-4), 7.04 (d, J=7.8 Hz, 2H, phenyl H-2 & H-6), 7.30 (dd, J=8.6, 7.4 Hz, 2H, phenyl H-3 & H-5), 7.50 (d, J=8.6 Hz, 2H, phenyl H-3′ & H-5′), 8.11 (d, J=8.4 Hz, 2H, phenyl H-2′ & H-6′), 8.23 (s, 1H, imidazo[4,5-b]pyridine H-5);

Provenance & Evidence