Trifluoroacetic acid → HCID 178432922, compound

Participants

Reaction Steps

tert-Butyl-4-(4-(6-bromo-7-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate (0.022 g, 0.033 mmol) was suspended in DCM (2.0 mL) and the mixture cooled in an ice bath. TFA (0.5 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 (5 g), washed with methanol and then eluted with ammonia (0.2M) in methanol. The filtrate was collected and the solvent removed in vacuo to give the title compound as a off-white solid (0.017 g, 91%); 1H-NMR (500 Mz, DMSO-d6): δ 2.26-2.36 (m, 4H), 2.61-2.75 (m, 11H), 3.50 (s, 2H, NCH2), 3.61-3.70 (m, 6H), 7.32 (s, 1H, thiazole 5-H), 7.45 (d, J=8.5 Hz, 2H, ArH, C6H4), 8.13 (d, J=8.05 Hz, 2H, ArH, C6H4), 8.23 (s, 1H, imidazo[4,5-b]pyridine 5-H); LC (Method B)-MS (ESI, m/z) 2.19 min—567/569 [(M+H)+, Br isotopic pattern]; ESI-HRMS: Found: 567.1634, calculated for C26H32N8SBr (M+H)+: 567.1654.

Provenance & Evidence