Trifluoroacetic acid → HCID 178432930, compound

Participants

Reaction Steps

tert-Butyl 4-(4-(6-chloro-7-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate (0.009 g, 0.036 mmol) was suspended in DCM (1.0 mL) and the mixture cooled in an ice bath. TFA (0.3 mL) was added and the resulting solution was allowed to warm up to room temperature and stirred for 2 h. The mixture was passed through an SCX column (2 g), washed with methanol and further eluted with ammonia (35% solution in water, 0.2M). The filtrate was collected and the solvent removed in vacuo to give the title compound as a solid (0.004 g, 21%); 1H-NMR (500 Mz, DMSO-d6): δ 2.41-2.49 (m, 4H), 2.62-2.70 (m, 7H), 2.87-2.94 (m, 4H), 3.56 (s, 2H, NCH2), 3.64 (s, 2H, NCH2), 3.67-3.74 (m, 4H), 7.32 (s, 1H, thiazole 5-H), 7.47 (d, J=8.0 Hz, 2H, ArH, C6H4), 8.11 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.13 (d, J=8.0 Hz, 2H, ArH, C6H4); LC (Method B)-MS (ESI, m/z) 2.09 min—523/525 [(M+H)+, Cl isotopic pattern]. ESI-HRMS: Found: 523.2155, calculated for C26H32ClN8S (M+H)+: 523.2159;

Provenance & Evidence