Trifluoroacetic acid → HCID 44160138, compound

Participants

Reaction Steps

Trifluoroacetic acid (3 ml) was added to a stirred solution of tert-butyl-4-[4-[6-amino-5-(1,3-benzothiazol-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (0.300 g) in dichloromethane (4 ml). The mixture was stirred for 1 hour, then concentrated under reduced pressure. The residue was dissolved in DCM (60 ml) and the solution was washed with a 0.5M solution of aqueous sodium hydroxide (30 ml). The organic phases were washed with water (15 ml) and brine (15 ml). The aqueous phase was extracted with DCM (3×30 ml), and then the organic layers were combined and concentrated under reduced pressure. The residue was stirred in acetonitrile (10 ml) for 18 hours. The solid was filtered and dried under vacuum. There was thus obtained 3-(1,3-benzothiazol-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (0.109 g); Mass Spectrum: M+H+ 377; NMR Spectrum: (DMSOd6 and CF3CO2D) 8.73 (d, 1H), 8.56 (d, 1H), 8.53 (s, 1H), 8.26 (d, 1H), 8.21 (d, 1H), 8.16 (s, 1H), 7.66 (dd, 1H), 7.59 (dd, 1H), 4.52-4.62 (m, 1H), 3.41-3.52 (m, 2H), 3.09-3.21 (m, 2H), 2.24-2.33 (m, 2H), 2.10-2.23 (m, 2H).

Provenance & Evidence